Eliot Path, Skyline to Hancock, Jeffries, Dalton, Raccoon Hollow (Blue Hills Reservation)

Eliot Path, Skyline to Hancock, Jeffries, Dalton, Raccoon Hollow (Blue Hills Reservation)

Hike Type: Criss-crossing Loop

Distance: 5.79 miles

Elevation: 1,145 feet

My Time: 2 hours

Book Time: 3 hours, 28 minutes

Parking: Ample parking at Trailside Museum
Hiking Challenges: Great Blue Hill Summits, Trail Trace the Blue Hills 2

The Hike 

I was feeling absolutely desperate for a redemption after yesterday's unpleasant hike. I decided to head down to the Blue Hills after my second to last Monday of the school year to hopefully get what I needed! The drive, naturally, had "heavier than usual traffic," and I was at the trailhead just before 3:40pm. I wasn't feeling like doing a Skyline Loop, so I figured I'd start on the Eliot Path and see where the wind took me. It was 81 and partly cloudy with an intermittent breeze, but the humidity was low and it was NICE. I guess summer can be okay?

The rocks on Eliot Path had a solid dusting of pollen on them, which made them slippery. I made my way up, visiting the ski spur before crossing the Summit Road. The ski trails were grown-in, so I cut through the woods to get both forks of the spur, hiking over many, MANY deer prints all around! I crossed the road and heard the first cicada of summer!

Just before Eliot Circle, I passed a woman in floral skinny jeans with a vastly different floral blouse on. She was actually super friendly, and told me about a family of deer she saw up here a few days ago, implying this floral-on-floral hiking fit was 100% on purpose - spectaular!

I played a little bit of Pokemon Go on Eliot Circle, and followed it all the way to the gravel path to the summit (counter clockwise). The area closest to the ski area was growing in, but by no means overgrown (yet). I worked my way up to the summit, potentially seeing a new gray bird (Update Pending)?

From the summit, I crossed the road and noticed a little path to a parking area, and then another path with a "no bike" plackard by DCR, so I decided to follow it! It was actually a wide, well-beaten path to the backside of the Eliot Tower pavillion - fun! I decided I'd hike the Skyline North to Hancock Hill, hit the Circle Trail, and then see what would happen after that. It was a beautiful day, and I was feeling good!

I made my way down to Wildcat Notch and found a DCR officer in an ATV looking lost or stuck on Puddle Path? She was on the phone with someone holding a map, and then slowly backed out... I wonder where she was heading? I crossed paths with a a family on Wolcott Hill that looked dressed for Houghton's Pond. 

The berries of all sorts were starting to grow in on Wolcott and there was more of that wonderful breeze. I was sweaty for sure, but I did NOT want to die, which was huge! As I descended into Downtown Crossing, I heard the ATV driving away again...

I worked my way up Hemenway, passing a cool snake shed on some of the rocks. I continued along, climbing up after Breakneck Ledge Path and then snaking my way through another family that was coming down towards Circle Trail. 

Up on Hancock's ridge, I noticed some of the blueberriers were starting to turn purple, and some even blue!! I hit the circle of the Circle Trail, which was a little grown-in, but I had my first handful of ripe blueberries of the season! Maybe summer isn't as awful after all...

I continued back into the woods on Circle Trail, enjoying more of a breeze as I made my way down towrads JeffriesTrail. I noticed some horse poop, which must have been a mistake becuase Circle Trail is a horse dead-end. The stream to Jeffries was absolutely bone dry, and higher up, the blueberries were still green. Good to know - Hancock's will be ripe by next week, but Jeffries' are probbaly another week behind. 

I made my way back up Hemenway Hill, and then I descended again on Hemenway Hill Path before hiking on the absolutely delightful Five Corners Path back to Downtown Crossing. I think I traditionally hike this stretch in spring during the melting season, so I've only ever been miserable on this stretch, so this was a win!

I hiked on the Skyline Trail back up Wolcott, trying to pick up the pace because the family was right behind me, and then I went down Dalton Path to get some more new trails. There are some bore holes on rocks near a swamp on Dalton, I wonder what that's all about? I guess either science or an old settlement, but this just feels like a strange place for it.

I hiked up Raccon Hollow, swatting away the only relentless bugs of the day, and then hiked the rest of Eliot Circle to finish out my second summit! I followed the road for a bit to play a little more pokemon, and then made my final descend on Eliot Path back to the car. This was the hike I absolutely needed!

Step-by-Step

- Park at Trailside Museum.

- Start hike on Eliot Path.

- Before road, turn right to ski area spurs.

- Return to Eliot Path at 1051.

- At 1055, turn right onto Eliot Circle.

- After 1030, turn left onto gravel path to summit.

- From summit, continue onto Summit Road.

- At path, turn right.

- Walk across parking lot, continuing onto unmapped path in woods (marked by a no-bike DCR plackard).

- At terminus, walk through Eliot Tower towards 1063.

- At 1063, turn left onto Skyline Trail North.

- After summiting Hancock Hill, hike the circle of Circle Trail clockwise, then continue on Cirlce Trail towards 1180.

- At 1180, continue onto Breakneck Ledge Path.

- At 1185, turn left onto Base Path.

- At 1182, turn left onto Jeffries trail.

- At 1150, turn around.

- At 1154, turn left onto Hemenway Hill Path.

- At 1140, turn left onto Five Corners Path (green).

- At 1141, turn right onot Skyline Trail.

- At 1117, turn right onto Dalton Path.

- At terminus, turn left onto Wildcat Notch Path.

- At 1092, turn right onto Raccoon Hollow Path.

- At terminus, turn left onto Eliot Circle.

- Before 1030, turn right onto gravel path to summit.

- From summit, continue onto Summit Road.

- Follow Summit Road.

- At 1051, turn left onto Eliot Path.

- Return to car.

Blue Hills Reservation Map

Photo Album

Skyline Trail Loop via Wright's Hill Trail (Middlesex Fells Reservation)

Skyline Trail Loop via Wright's Hill Trail (Middlesex Fells Reservation)

Hike Type: Lollipop Loop

Distance: 8.18 miles

Elevation: 1,089 feet

My Time: 2 hours, 48 minutes

Book Time: 4 hours, 38 minutes

Parking: Parking for ~15 cars at Bellevue Pond.
Hiking Challenges: 52 Hike Challenge 2026, Middlesex Fells Skyline Trail, Operation Alaska Benchmark Challenge

The Hike 

The end of the school year has been mentally beating the life out of me, so I decided it was time to physically beat myself up too and revist the Middlesex Fells Skyline Trail. I hiked the loop once before, but I did missed the final segment coming down from Wright's Tower, so I guess I had never officially hiked it all. Plus, I found a patch for it on Ebay! It seems to be an older Boy Scout patch, but it still counts! It was warm out in the low 80s.

Bellevue Pond had become mostly a grassy meadow now with just a very small pool of water in the back. I hiked in and decided to take the Wright's Tower Trail first to access the Skyline Trail for views and a little bonus elevation. This was also the pollen-iest day of the year - I was already coated in the yellow toxins. The sunny part of the trail was HOT. The shade was okay. I made my way up and ran into a bunch of teens, so I took my picture at the view and blasted off! I liked seeing the view of Boston in it's new green foliage.

Now officially on my loop, I admired how shaded the woods were. As I climbed up and over the first little knob after D6-2, I passed some baby blueberries. I had to really pay attention to blazes since there are so many criss-crossing paths in the Fells, many of which are not even on thge map. I passed a very stinky duo, which was crazy, because usually I'm the stinky one!

I worked my way up and over the Panther Caves and then passed a bone-dry swamp just after. I took a swig of my warm Nalgene and hit the junction with the Cross-Fells Trail right at the first mile marker. It was fun to hike in this area, it felt a bit like Memory Lane! There was a little swamp before C5-1 and the first of many confusing junctions - which is always my beef with the Middlesex Fells - blazing is either aggressively abundant or severely lacking, and there is simply no in-between.

The Skyline Trail paralleled the Mountain Bike Loop in a swampy area and then joined on a gravel path, then passing a concrete water tank(?) and a stone block in the ground that might mark the town line btween Winchester and Medford, even though it didn't exactly match the map. I descended to West Dam Road, which had a small wetland with a very shy turtle. There were a few annoying bugs buzzing about, but not enough to warrant bug spray.

The trifecta of the Skyline Trail, Reservoir Trail, and Mountain Bike Loop coincided and rose steadily on a gravel path after crossing West Dam Road, and later Skyline and Reservoir veered left away from a metal water tower, splitting from each other a minute or so later. I could feel the pollen granules in my eyes and a large amount of spider webs on my skin. 

I was enjoying this western portion of the loop becuase I had hiked most of it previously in winter, so I really wasn't recognizing most of it! I was also atonished how in the right lighting I could see how thick the pollen was in the air. I climbed up and down another knob to cross Molly Spring Road, and I could hear an owl when I was working my way up and over Nanepashimet Hill, which was SUPER sunny.

There was an old metal beam and rock harlqeuin flowers on the knob after B3-12, and then I had to maneuver a few blowdowns before B3-6. I passed a big cloud of what smelled to be the Devil's Lettuce, but the source was unknown. I could start to see the reservoir though the trees, which was exciting!

I've always been confused about the roads around the reservoir. It seems the roads circling the North Reservoir are open, and were signed as such, even though they're resitricted on the map. I crossed paths with a wild amount of shirtless trail runners in running vests in this stretch, which had really pretty flat pine-y woods.

As I hiked along Hillcrest Parkway, I admired some of the massive hydrangeas in peoples' yards. There is also a good amount of roadside parking here, which was good to know. I hiked past the North Reservoir's dam, which is closed to the public, and I eavesdropped on a duo's gossip session about a friend who inherited a bunch of money recently, it was a very fun 10 seconds!

The Skyline Trail goes back into the woods and zig-zags down to the reservoir's outflow stream, which was just a trickle. I crossed the creek on a NEMBA bridge, enjoyed a nice breeze, and began to make my way towards the Bear Hill Area, which was still pretty foreign to me. 

I almost got lost at C1-4 due to an unsigned and unblazed turn, but thankfully my brain thought "this feels wrong." The trail hit a low point just after with some rotting bog bridges just before rising to the Dike Road.

I climbed up the side of Bear Hill, passing an older hiker and his well-behaved and possibly overheating golden retriever and after the height-of-land, the trail became full of a wonderful, floral scent with no flowers to be seen!

As I approached the Sheepfold area, the Skyline Trail became more of an open trail, crossing knob after knob, many of which were open, and they were HOT. Winthrop Hill had a sunny bench overlooking some grasses at the top, and I almost got lost again at D3-1.

I maneuvered around an impressive blowdown just after C2-8 and then skimmed the outside perimeter of the Sheepfold area next to a swamp. There seemed to be a good amount of folks out at the main Sheepfold area, but the Skyline Trail was still full of spiderwebs! I was happy to be in the shade, though.

The Skyline Trail briefly followed a paved path as I-93 roared in the distance. The trail cut through a parking area, crossing a couple of paved single-land roads, and then turned left onto a nice boardwalk. I noticed a bit of a hot spot on both of my big toes and right heel, but naturally decided to avoid it. I felt myself finally starting to tire out around the six-mile park, but I kept on moving!

I joined the Cross-Fells Trail again and almost got lost... again soon after. The Cross-Fells left soon after joining and I officially finished all my water (only 1L, oops) on Silver Mine Hill. It was hotter than I was ready for! I joined the Cross-Fells yet again at C5-18 and crossed paths with a trail running trio I saw over by the North Reservoir - only this time they were power hiking. The two guys were leading and the woman was suffering behind, I felt kind of bad for her.

I finally made it to my final push up to Pine Hill and I was tired! Eight miles after school in the heat took more out of me than I was ready for! I decided to look for all three discs again: I found the northernmost one, an arrow, and it was pointing to a summit disc. But... I don't think I'd seen this one before? On a higher rock to the east was another arrow, which I think I had seen before. Wait this is three? I already knew about the magnetic station, so there's four up here? I worked my way over, and found ANOTHER arrow?! Five discs?! This was beyond exhillerating to me and fully brought me back to life. 

Riding the high of discovery, I continued onto the tower and was SHOCKED to see how insane the pollen haze had become - it was so thick I couldn't even see the Blue Hills! 

From here, I descended back along the yellow trail and made it back to the car, dusting myself off before driving back home. Another patch "earned"!

Step-by-Step

- Start hike on Quarry Road.

- At jct., turn right onto Wright's Tower Trail (yellow).

- At tower, turn left onto Skyline Trail (white).

- Follow Skyline Trail clockwise around, back to tower.

- At tower, descent via Wright's Tower Trail (yellow).

- At terminus, turn left onto Quarry Road and return to car.

Middlesex Fells Reservation Map

Photo Album

Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Hike Type: Mostly Lollipop Loop

Distance: 4.54 miles

Elevation: 640 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hour, 35 minutes

Parking: Room for 20-30 cars at Chickatawbut Overlook.
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Blue Hills Grid

The Hike 

I made my way back to the Blue Hills after school, suffering through another afternoon of "unusually heavy traffic." The inspiration for this hike was the Blue Hills Grid that I've been "working" on for years now, plus my second Trail Trace map. I had field day today, so I had been outside for a lot of the afternoon, but I was excited to keep the momentum going! It was 78 degrees out and overall pretty pleasant!

I made my way into the woods and up to the tower before following the yellow blazes counter-clockwise. I stopped for a quick potty break and managed to pee on my hip belt strap... Ugh. I worked my way up Thayer Path, which was grassy up around the summit fence (I had tick anxiety). I went down Carve Path, which had it's trademark giant rock piles that I've always been wildly curious about. 

I then made my way down onto the Bouncing Brook Path, which I'd be following for a while. It was darker and more humid down there, and I was following horse prints for most of the walk. I passed some lovely purple flowers, which were lesser periwinkle, not violets. I passed a really nice stone wall I hadn't noticed before just before the junction with Lee Path, and then a lady slipper just before the junction with Sassaman! Just kidding! At the junction with Curve Path! I missed a turn! That's fine, my hike was going to be a bit longer.

Everytime I'm hiking these interior Chickatawbut trails I'm reminded of how long they feel - it must be because there's a thinner density of trails in this area, or something. The bugs were present but not much of a bother as long as I kept on moving. I worked up Wampatuck Path and then the Pocapawmet Path to join the Skyline Trail!

I don't think I have traveled this direction on the Skyline Trail since a hike with Gen and Wylie in the winter of 2021 or 2022 - it's been a minute! I passed a super cute eastern towhee on my way up Broken Hill #4 and then maneuvered the rockiness that surrounds #3 - there were baby blueberries! A deer magically lept across the trail as I was climbing up #2 and there were some young rock harlequin flowers at the top. 

The climb up #1.5 was also rockier than I had realized traveling in the other direction, and I found myself wondering how different the forest would be on #1 in 10, 20, 50 years since the last fire. It looked like most of the pines were dead/dying and the undergrowth was growing in strong! I passed more pink lady slippers and rock harlqeuins as I descended #1, and then I started my climb up Nahanton.

The climb up the Chickatawbut Ridge was actually more gradual than I was emotionally ready for. I climbed on up Nahanton, past some more baby blubes, and found myself wondering yet again about the old foundation-like things. I admired the stone steps up Kitchamakin and suffered through the brush to reach the true top of Fenno Hill before making my way up to Chickatawut Hill. I descended via Stowe Path and made it back to the car - this was officially a zero-person hike! I dusted the pollen off of myself (literally) and heard a barrel owl calling somewhere on the other side of the road.

Step-by-Step

- Park at Chickatawbut Overlook.

- Start hike on Tower Path (yellow).

- At 3075, turn left onto Sassaman Notch Path (yellow).

- At second jct., turn right onto Thayer Path.

- At fence, turn left.

- At second jct., continue right onto Skyline Trail (blue).

- At 3065, turn left onto Carve Path.

- At 3051, turn left onto Bouncing Brook Path (red). 

- At 3152, turn left onto Wampatuck Path.

- At 3171, turn around and turn right onto Pocapawmet Path (unmapped).

- At terminus, turn left onto Skyline Trail (blue).

- At Chickatawbut Hill, turn right onto Thayer Path, then turn right again onto Stowe Path.

- At jct., turn left to stay on Stowe Path.

- At terminus, turn left onto Sassaman Notch Path (yellow).

- At 3075, turn right onto Tower Path (yellow).

- Follow Tower Path back to car.

Blue Hills Reservation Map

Photo Album

Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Hike Type: o-O Loop

Distance: 4.97 miles

Elevation: 1,220 feet

My Time: 1 hour, 46 minutes

Book Time: 3 hours, 5 minutes

Parking: Ample room at Trailside Museum
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Great Blue Hill Summits

The Hike 

Happy Pride Month! It was time to officially begin my second Trail Trace the Blue Hills Map! I had a dreadfully sleep drive with "heavier than usual traffic," landing at the Trailside Museum at 3:35. There were very few cars, which brought me joy! I was planning on just doing a fitness hike with a possible detour to get the full red-circle route for my new map, we'll see! It was sunny, 62 degrees, and there was a light breeze. It was lovely!

Somebody unfortuantely got started right before me, but I had to pull off to pee anyway. I eventually caught up and passed him and continued my way up. There were a bunch of leaves on the ground after Saturday's storm. My legs were in a weird mood, feeling a bit like a baby deer learning to walk. I couldn't really get a rhythm together on my climb. Thankfully, I could hear a bunch of eastern towhees, which made it feel better!

I passed a bunch of white daisies after summiting the first time. The work on the summit area has been continuing, with another widening of the Eliot Circle for trucks (I assume). I made my way onto the Skyline Trail North, admiring how shaded it is this time of year. Naturally, I was gassy on this hike, and at one point I made three stomps, farting on each stomp, and the pitches of each fart were different and accurately mimiced the final three notes of the University of Massachusetts Minuteman Marching Band's rendition of Frank Sinatra's My Way - it was remarkable.

I worked my way up and over Wolcott, Hemenway, and then Hancock. My body was just feeling tired and heavy, maybe because I had wine before bed last night? I passed some beautiful blue jays coming down Hancock Hill and I was simply not emotionally ready for the climb up Houghton. Thankfully, the climb did not humble me as badly as I thought it would. I did gas me out, but I was not passing away.

The leaves made the Skyline Trail super dark at the first stream crossing, and to my absolute delight I found some lady slippers between 1123 and the Five Corners Path!! This is where I usually find them this time of year, so I was just elated.

The second stream crossing was fully dried up and I noticed a path straight ahead before the crossing to what looks like a cave? I had never noticed it before... interesting! I made a note of it, being too lazy to investigate. I zig-zagged up to the final headwall, suffered on up, and then continued up along the shoulder for the final push, which always feels longer than I am ready for!

I listened to the northern house wrens at the summit (thank you, Merlin!) and decided to follow the other half of the red loop for my trip down, which was lovely. The swamp along the trail was mostly dry, and it looked like DCR is working on formally closing a few of the abandoned trails in that area. My final stretch of trail was cheered on by a friendly Robin, which was just lovely.

Step-by-Step

- Park at Trailside Museum.

- Start hike on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle.

- At summit road, turn left.

- At jct., turn right.

- At summit, hike around observatory clockwise, following gravel path.

- At terminus of gravel path, turn left onto Skyline Trail (blue).

- At 1063, turn right onto Skyline Trail North.

- At Hillside St., turn right onto Hillside Street.

- At jct.,. turn right onto Skyline Trail South.

- At 1066, turn left onto Eliot Circle/Skyline Trail.

- At gravel path, turn right onto Gravel Path.

- At summit, continue straight and hike spur towards ski trail.

- At jct., turn right onto Eliot Cirlce.

- After 1055, turn left onto Raccoon Hollow Path (red).

- At 1082, turn left onto Cliff Trail (red).

- Cross Summit Road, continue onto Trailside Path (red).

- Follow red dots back to car.

Blue Hills Reservation Map

Photo Album

Braintree Triangle (Blue Hills Reservation)

Braintree Triangle (Blue Hills Reservation)

Hike Type: Lollipop Loop w/ Loop

Distance: 1.62  miles

Elevation: 46 feet

My Time: 29 minutes

Book Time: 49 minutes

Parking: Room for 4-5 cars at trailhead.
Hiking Challenges: Trail Trace the Blue Hills

The Hike 

Now it's 5:40pm the day after Memorial Day. I just had a very successful hike of the quarries, and I'm officially on my final hike of my Trail Trace the Blue Hills Patch! I hiked the bit of Old 128 to the right of the parking area, and then worked my way onto the Hemlock Path, where the robins were cheering me on. I was feeling slightly miserable from the wet cotton as I collected more and more spiderwebs, but there was a nice breeze keeping an ounce of life in me. 

On the return from Hemlock, I noticed that my watch was frozen? I had to do a soft reset (for the first time) to get it to unfreeze. When it was back on, I restarted my activity, but it wasn't tracking distnace or elevation... Naturally the final hike of my map wouldn't have a Garmin map... Literally fine, just annoying!

I made my way onto the Braintree Pass Path and enjoyed seeing across the highway to the other side - I always love imaginging what it was like pre-93. I finished the little loop and had a nice walk back along Old Route 128. I noticed 5614 was still marked in-person for the Laurel Path, but it is not on the most recent DCR map. Just when I was getting mopey about still walking, I remembered that I officially completed my map! This marks the fourth time I've hiked all the trails (twice for the Friends of Blue Hills patches and once for a Winter Trace). I'll definitely be taking a sick day tomorrow to celebrate...!

Step-by-Step

- Park at 5620.

- Start hike turning right on Old Route 128.

- At West Street, turn around.

- At 5620, turn right onto Hemlock Path.

- At terminus, turn around.

- At 5620, turn right onto Old Route 128.

- At 5611, turn right onto Braintree Pass Path.

- At 5610, turn left onto Winnemoiset Path.

- At 5600, turn left onto Old Route 128.

- Follow Old Route 128 to car: Trail Trace complete!

Blue Hills Reservation Map

Photo Album

Quarries Foot Path & Quincy Quarries (Blue Hills Reservation)

Quarries Foot Path & Quincy Quarries (Blue Hills Reservation)

Hike Type: Spaghetti Loop

Distance: 4.13 miles

Elevation: 449 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hours, 17 minutes

Parking: Room for one car at pull-off at 4223.
Hiking Challenges: Trail Trace the Blue Hills

The Hike 

'Twas the Tuesday after Memorial Day and I only had a few trails left of the Blue Hills to hike for my patch, so I took a deep breath and had a dreadfully sleepy drive to the Quarries after school. I was simply not excited about this hike, but this and Braintree Triangle were all I had left! It was a warm day in the low 80s, I forgot to bring a wicking t-shrit so I was stuck in an awful cotton shirt, I applied my bug spray, and got to work!

Things actually got off to a wonderful start when I saw blazes! I remembered reading that the Friends of the Blue Hills got approval to blaze the trail - I was hoping for paint blazes, but instead they blazed the trail with laminated papers with a geometric "Q" stapled to trees.

One minute in and I was already fully covered in spiderwebs. I hiked past some yellow star grass (thank you, Seek!) and made my way into the woods, up and over a longtime annoying blowdown, and soon approached the famous confusing slabby part. There was some nice stone work leading up to the scramble. The blazes had been clear up until this point, but it was again unclear of how to get up. I went up the way that I always have, and it seems that I had been doing it the right way?

There was a lull in the blazing for a minute with only a few traces of flagging tape (which is why I think paint blazes would have been a better move). This whole area is so cool. If they could clean it up, maintain the trail, and somehow change the culture around partying in this area, it would be a really wonderful area.

I learned that the way to stay on-route is to just follow the high ridge until a viewpoint, and then veer left to descend (there was a blaze on a tree here). I successfully got the spur to Adams Path and then the spur that looped back upon the Quarries Foot Path. I was actually feeling good!

I was feeling very good except for the hellscape that was the soaking wet cardboard-esc cotton on my skin. I made my way over to that awfully grown-in meadow, and was rewarded with a deer! There were also a comical amount of orange moths simply... making love. I made my way back to the Quarries Foot Path and then the final loopty loop nearest 4238, which was mostly marked with flagging tape (thankfully). I finished out the Quarries Foot Path, which appeared to now cross Riccuiti Drive, which had a sign! The sign on the opposite side of Riccuiti Drive read: "The Quarry Trail winds through an area previously dotted with granite quarries. Between 1815 and 1956, numerous quarry pits operated in this area. The Quincy granite industry led to innovations in quarrying techniques. Famous for its quality, Quincy granite was shipped throughout the United States and the world. Laborers came to Quincy from northern New England and from Europe to work in the quarries, transforming Quincy from an agricultural community to a major industrial center. From 1997 to 2001, the largest quarries were filled with dirt from the Big Dig project in Boston."

I hit the bits of trail on the western edge of this side and then worked my along toward the spur path that led to the main Quincy Quarries parking area, passing some interesting looking folks on the way. The main quarry area was super cool per usual - the graffiti has transformed from "crime" to real art, and the view from the top is really cool! There was a guy at the tippy top, so I left him alone. I had to be careful, though, because the paint-covered granite was slippery. 

Now I was going to work my way around this area clockwise, starting by following the path around the flooded quarry near the road, which had a spray-painted metal sign with the geometric "Q" on it! There were a few mallards on the algae-filled pool. I worked my way up the trail, passing another metal "Q" and a small green sign high up on a tree - it's clear they've put some work into this area. 

The trails in the northeast corner were almost painfully overgrown, but I got them done! I followed the trail around the flooded tall quarry in the northeast corner of the park, enjoying the views on the way! The trail turned left off of the high wall just before a slight uphill to the highest point.

In the back section, I am always interested in the trails that are not on the map, but I was not ready to be exploring! I made my way down to the Incline Railway and read the following message:

"Quarry Museum Open June

The Quincy Quarry and granite Workers Museum will be open on Saturday, June 6th and Sunday, June 7th from 11 to 4 for a self-guided walking tour at the Lyons Turning Mill and museum located on 20 Quarry Hills Drive, West Quincy. Historic pictures of the granite industry and interpretive information can be viewed at each stop around the mill. The museum will be open to view pictures and artifacts from Quincy's granite industry. Come visit our indoor, outdoor and geology museums. Museum members will be on hand to answer questions and Quarry Museum T-Shirts will be on sale to help support the museum. The quarry museum, Lyons Turning Mill and geology building is open the first full weekend and 3rd Saturday each month through November. Come visit an learn Quincy's granite history Free admission"

I wrapped up this upper portion of the quarries, crossed Riccuiti Drive again, and continued my journey, circling around another quarry and hitting the unfortunately overgrown loop near Douglas Street. For the last couple of minutes in this loop, I also had the distinct pleasure of following a turkey that simply would not get off of the trail. It gobbled at me initially, but wouldn't do it again for the camera. It eventually ducked out right at the close of the loop to join it's turkey friends, and then I made my way onto the Adams Path and then Bunker Hill Lane! This was the most successful trip to the quarries ever! I decided I'd reluctantly drive to the Braintree Triangle to finish out my map. It was a nice day, and I think I'm calling out sick tomorrow...

Step-by-Step

- Park at 4223.

- Start hike on Quarries Foot Path (blazed with Q).

- Round the wide corner by the "t" on the map, and hike the. mini loop.

- After, hike the trail that connects to Adams Path.

- At Adams Path, turn around.

- Continue on Quarries Foot Path, hiking next mini loop and spur to 4236.

- At 4236, turn left.

- At terminus, turn around.

- Return to Quarries Foot Path.

- At second junction (before 4238), turn right.

- Follow flagging and AllTrails to hike path.

- At terminus, turn right onto Quarries Foot Path.

- At 4238, hike triangle and turn right.

- At terminus, turn left.

- At terminus, turn around.

- At Ricciuti Drive, turn around.

- At jct., turn left.

- At 4238, turn left onto Quarries Foot Path.

- At Ricciuti Drive, turn around.

- At 4238, turn left.

- At jct., turn left and cross Riccuiti Drive.

- First, hike to top of Bunker Hill Quarry (easternmost).

- Then, go back to pavement and hike Quarry Trail around pond.

- Hike trails on west side, then hike to 4229.

- At 4229, turn left.

- At terminus at Granite Railway Museum, turn around.

- Return to Riccuiti Drive and cross at same spot.

- At terminus, turn left.

- At jct., turn left onto Adams Path.

- At road, turn around and then turn left.

- Hike mini loop near Douglas St.

- At end of loop, turn left onto Adams Path.

- Follow Adams Path to 4235.

- Continue onto Bunker Hill Lane.

- Turn right onto Furnace Brook Parkway to end hike.

Blue Hills Reservation Map

Photo Album

Cross Path, Whip Hill, Crystal Spring Path/Road (Middlesex Fells Reservation)

Cross Path, Whip Hill, Crystal Spring Path/Road (Middlesex Fells Reservation)

Hike Type: Spaghetti Loop

Distance: 3.71 miles

Elevation: 427 feet

Time: 1 hour, 15 minutes

Parking: Ample parking at Greenwood Park in Stoneham.
Hiking Challenges: Middlesex Fells Reservation

The Hike 

I take back every complaint I've made about heat in 2026 (that's a lie), because it was officially HOT. I was getting an after-school hike in at the Fells on a STEAMY 94-degree day. Ouch. To make things worse, the porta potty at Greenwood Park was gone! My goal was to connect the final dots in this area of the Fells, but acknowledged that it was miserable out and wasn't going to push myself too hard. I got suited up and off I went!

I was sweating 50 feet away from my car, and then passed a massive group of hikers (looked like a guided hike) before turning onto Whip Hill Road, which donned a bunch of wonderful flowers! The humidity cranked up whenever the trails paralleled wetlands, which felt... unpleasant.

I continued onto Cross Path, hiked the triangle at F2-8, and then worked my way onto the other Whip Hill trails that don't go over the top. I heard a barred owl through the trees, but sadly didn't see it. There was an interesting man (or alien)-made fence made of fallen limbs going up Whip Hill, and once I was over the other side I had a sip of hot Nuun, which is never pleasant. I meandered around, eventually landing back on the giant split rock at F2-15 before hitting some more new trails.

Whip Hill Park was FULL of blooming mountain laurel, which was just a delight to see. There were also a couple turkeys on the trail that descends to Gate 47 - one was gobbling up a storm and was HUGE. The trail passed a few back yards before hitting the gate, where I turned around to continue my wander.

I passed some robins baithing in a little drainage stream and worked my way on the littles uphill on the Crystal Spring Path, where my nose started to bleed! Yikes. I did a little loop, went uphill again, and then descended to Crystal Spring Road, which was mostly paved and lined with flowers - kind of lovely!

After bouncing around at the parking area off the Lynn Fells Parkway, I landed at Gate 41 and walked along Pond Street to hit my final stretch of trail, which was blazed for the Crystal Spring Trail, which didn't match the map (annoying). I also noticed a wooden rectangular post that said Saddleback Path on it at the road - I wonder if there's more of these throughout the park like at the Blue Hills?

I hiked uphill to the green blazes and to my delight was just about done! I was COOKED. I'm so not ready for summer summer (I AM ready for summer vacation, though). I made it to Christien's and immedaitely took my first cold shower of the season!

Step-by-Step

- Park at Greenwood Park

- Start hike on red-blazed Crystal Springs Trail northbound.

- At E2-1, turn right onto Whip Hill Road (green).

- At F2-3, continue onto Cross Path.

- At F2-8, hike triangle, and then turn left onto Crystal Spring Path.

- At F2-9, turn left onto path.

- At F2-10, hike triangle and then turn right (green).

- At F2-14, turn left.

- At F2-13, turn left.

- At F2-1, continue straight.

- At E2-9, turn left onto Whip Hill Path (green).

- At F2-2, turn left.

- At F2-10, turn left (green).

- At F2-14, turn left.

- At F2-15, turn right (green).

- At F2-16, turn left.

- At F2-17, stay straight (do not enter Whip Hill Path, follow path along homes).

- At Gate 47, turn around.

- At jct., turn left onto Crystal Spring Path.

- Hike spur between F2-20 and F2-19, then continue on Crystal Spring Path.

- At F2-18, turn right.

- At F2-17, turn right.

- At jct., veer right.

- At F2-19, turn right onto Crystal Spring Path.

- At F2-6, turn left onto Crystal Spring Road.

- At Lynn Fells Parkway, turn around.

- At Gate 41, turn right onto Pond Street.

- At jct., turn right onto Saddleback Path.

- At E2-6, turn left (green).

- Follow green blazes back to car.

Middlesex Fells Reservation Map

Photo Album

Nahanton Hill, Reservoir, Sassaman Notch Path (Blue Hills Reservation)

Nahanton Hill, Reservoir, Sassaman Notch Path (Blue Hills Reservation)

Hike Type: Lollipop Loop w/ Lollipop Spur

Distance: 4.17 miles

Elevation: 522 feet

My Time: 1 hour, 30 minutes

Book Time: 2 hours, 20 minutes moving

Parking: At Chickatawbut Overlook.
Hiking Challenges: Trail Trace the Blue Hills

The Hike 

"Heavier than usual traffic on your route" - Google Maps, again.

I was going back and forth on getting a hike in on this Wednesday afternoon. Traffic was abhorrent and I was already getting out late, but I rallied. It was going to be the last nice day until the weekend and I knew I'd feel better if I sucked it up. I made it to the Chickatawbut Overlook trailhead at 4:20pm (horrible). Thankfully, it was a nice partly sunny day at 67 degrees with a breeze - could be worse. The main objective for the day was the Blue Hills Reservoir, one of my three last sections - anything else would be a bonus - off I go!

As a gace of god, my mood was turned around 2 minutes into my hike when I heard the beautiful song of a Baltimore Oriole (thank you, Merlin)! I hiked the Tower Path over to the rock stairs on the back side of Nahanton Hill - I was determined to see a view! The blueberry and other bushes were starting to bloom, which made for a very scenic mini climb. My legs were feeling a bit tired from my first leg day in like six-ish weeks (and it was a weak leg day at that), so I was moving slow and steady.

The view from Nahanton showed hazy clouds north of Boston with mostly blue skies south - fun to see! I made it down and up the first Broken Hill, which is always a favorite of mine. The tent catepillars were also loving the first Broken Hill. The swamp between #1 and #1.5 was fully dried up, and just after I turned left onto the Squamaug Notch Path, which had even more tent catepillars and some red columbine flowers that I had never seen before (thank you, Seek!). I turned onto the Ridge Path and then started my loop around the Reservoir.

The path around the Reservoir that follows Chickatawbut Road was actually in great shape - I feel like my legs usually get tickled the entire time, but I had no tickling to speak of! There were a couple of fishermen on the wooded side along with what I believe to be a Great Egret. It was windy on this loop, but all nice.

The egret flew away as I got closer, naturally. I walked along the dandelion-lined path parallel to the woods, hiked the penninsula (the reeds that usually block the way were flattened - maybe from this year's snow?), and passed the two fishermen, who seem to have become friends! I then worked my way back to Squamaug Notch and the Skyline Trail to finish out the Broken Hills.

I hiked the Pocapawmet and Wampatuck Paths, landing on the Curve Path. The swamp that the Curve Path follows had some wildlife commotion going on, but I was not planning on finding out what it was! I decided to make my return via the Sassaman Notch Path, which is a really pretty old road. It makes it fun to imagine what life was like when it was an actual road proper. The path was a bit of a slog after a while, but eventually I was back in the notch, passing the tower, and back to my car!

Upon plugging this hike into my spreadsheets, I found that this was my 200th hike in the Blue Hills! How fun!

Step-by-Step

- Park at Chickatawbut Overlook.

- Start hike on Tower Path (yellow dots).

- At tower, turn left on Tower Path (yellow dots).

- At terminus, continue onto unnamed path up Nahanton Hill.

- At split, turn left.

- At 3103, continue onto Skyline Trail eastbound (blue rectangles).

- At 3144, turn left onto Squamaug Notch Path.

- At 3131, turn right onto Ridge Path.

- At Chickatawbut Road, turn right.

- Continue on path along road, hike around reservoir clockwise.

- Return to Ridge Path.

- Turnleft onto Ridge Path.

- At 3131, turn left onto Squamaug Notch Path.

- At 3144, turn left onto Skyline Trail (blue rectangles). 

- Before Chickatawbut Road, turn right onto unmapped Pocapawmet Path.

- At terminus, turn right onto Wampatuck Path.

- At 3153, turn right onto Curve Path.

- At 3135, turn right onto Sassaman Notch Path (red dots).

- Follow Sassaman Notch Path past the turn of red dots, turn left onto Tower Path (yellow dots).

- Return to car.

Blue Hills Reservation Map

Photo Album

Green Hill Path, Field Path, Orchard Trail (Blue Hills Reservation)

Green Hill Path, Field Path, Orchard Trail (Blue Hills Reservation)

Hike Type: Spaghetti-ish Lollipop Loop

Distance: 2.47 miles

Elevation: 118 feet

My Time: 51 minutes

Book Time: 1 hour ,17 minutes

Parking: At end of Royall Street.
Hiking Challenges: Trail Trace the Blue Hills

The Hike 

Monday afternoon! I had a brutally slow and sleepy drive after work (I don't know why Google insists on saying "slower than usual traffic" when the traffic is always slow), fully fueled by leftover cheerios. Skies were grey, temps in the low-60s, and I was very low on energy. Thankfully, I had a small hanging chad that I needed to get done, no matter how much I didn't want to do it. I parked at the end of Royall Street and hiked right into the woods to meet up with the western end of the Skyline Trail, which was full of spiderwebs. 

On a plus, the Skyline Trail follows a wonderful stone wall before crossing a highway drain outflow surrounded by garbage... Anyway, I continued onto the abandoned interchange, past the... flooring(?) that has been decomposing for years, and made my way back into the woods at the start of Green Hill Path. To mix things up, I decided to hike Field Path counter-clockwise, yay?

Field Path has notoriously been one of, if not the most overgrown trail in the reservation. To my delight, some of the blowdowns have met a saw in the past couple of years! It actually used to be much worse. There was a good amount of unavoidable vegetation, but thankfully i made it out without ticks. The footing transitioned from leafy/stick-y to grassy, which was unpleasant in a different way. The only fun part of this trail is the little blowdown tunnel you get to hike through. The field that the trail might be named after appeared to be covered in pricker bushes now... bummer.

There were a few easy step-over blowdowns at the end, and I was free! The return on Green Hill Path was very leafy, but fine otherwise. Onto Orchard Trail, there was a LOUD flying insect near the beginning, and delightfully nothing elsewhere. This was in the best shape out of all three trails back here. I returned again on Green Hill, through the interchange, back onto the Skyline Trail, and at the same junction where I turned onto the trail, I veered right (not turn right, to be clear) onto the final trail I needed in this area - just a spur from Skyline to Royall Street. At the terminus, there was a sign pointing towards the Skyline Trail and Fowl Meadow - fun!

I could have driven over to Brookwood to get another hanging chad, but my energy was dreadfully low and all I wanted was to get my chicken from Costco and go to bed, which is EXACTLY what I did!

Step-by-Step

- Park at the end of Royall Street, enter woods on unmapped path.

- At terminus, turn left onto Skyline Trail.

- Follow pavement to Green Hill Path.

- At 6102, turn left onto Field Path.

- At 6103, turn right onto Green Hill Path.

- At 6102, turn left onto Orchard Trail.

- At 6104, turn left onto Green Hill Path.

- Follow path and pavement back to Skyline Trail.

- At terminus of the spur hiked in the beginning, follow different spur left to Royall Street.

- At terminus, turn right on Royall Street, return to car.

Blue Hills Reservation Map

Photo Album

Ponkapoag East, Hemlock Road, Randolph Path (Blue Hills Reservation)

Ponkapoag East, Hemlock Road, Randolph Path (Blue Hills Reservation)

Hike Type: Spaghetti Loop

Distance: 8.03 miles

Elevation: 420 feet

My Time: 2 hours, 18 minutes

Book Time: 4 hours, 13 minutes

Parking: At Donovan Elementary School (weekends).
Hiking Challenges: 52 Hike Challenge 2026; Trail Trace the Blue Hills

The Hike 

I feel like we keep having rainy weekends! I didn't get out hiking yesterady due to... RAIN, and I had plans today with Christien in the afternoon, so my only window was a morning in the Blue Hills. Thankfully, I still had one more medium-big section left of my map, so off to Randolph I go! It always feels strange going to Randolph, since I used to work there. I parked at the Donovan school, booted up at the car, and was on my hike! It was a cool 54-degree morning full of wet plants and clouds overhead. I threw some bug spray on (the first of the year!) just in case I caught any ticks. I also needed a few hanging chads on the main Ponkapoag side, but wasn't going to get married to that idea - one thing at a time!

My hike started on Meadow Road and then on an unmapped connector and then unnamed trail, both of which had plenty of horse poop. I hiked the unique trails around the Ladybug Trail, Sumner Path, Cranberry Circle, and Coolidge Path (and fought for my life to stay on the correct trail, as there's a bunch of random paths), did NOT spook a deer right off of the trail, and then worked my way over to the old ballfields. There was SO MUCH horse poop.

To no surprise, Pasture Road was muddy. Not super wet-wet, but very muddy. The slippery kind of mud that you don't expect, and suddenly you're mudsliding three feet ahead. I turned onto the first unnamed trail at 5424 and noticed that this area was recently burned! According to Facebook, just a few days ago, which made sense since the smell was pungent. I was sweating from the humidity (and probably from dodging poop), and loopty-looped my way around this area, running into another deer at the footpath end of Pasture Road! There was also some impressive Japanese Knotweed.

Once I survived, I returned to Pasture Road and made my way to the Pequimmit Trail, following muddy deer tracks on the way. Pequimmit Trail was nice and dry and bisected another unmapped trail on the way to the Pipe Line. I passed some young tent catepillars and started a long figure-8 loop, turning left onto the Pipe Line, hiking the triangle at the base of the horse bridge, and then continuing onto the Wannamanhut Path. The sun would poke through occasionally, followed by another patch of darker clouds. The trail came near Route 24, and when it ended, I turned left onto Middle Road, which came to a hole in the fence SUPER close to 24. Spooky! I turned around here, crossed the Pipe Line, and continued onto the main part of Middle Road, which had a few criss-crossing trails not on the map. One day I WILL explore the Nike area, but not today.

I crossed Middle Street and continued onto an unmapped footpath. When it terminated, I turned onto the seldom-used eastern spur of Smith Trail, which gently rose and steeply dropped to some private property at an impressive rock (I almost fell down the steep drop, oops). I turned around, hiked to the Pipe Line, hiked the Pipe Line to I-93, and then turned around and hiked the full Pipe Line all the way to MA-24. Naturally, the last bit after the horse bridge entrance was the worst, but it wasn't unbearable, at least?

After my grassy excursion, I did push onto the main Ponkapoag area, where I only needed a few trails (including another bad stretch of the Pipe Line). I crossed the horse bridge, hiked Vose Path (both branches), and then continued along Hemlock Road. Just before the Pipe Line junction, there was a comically deep... dry? mud pit? Like it wasn't dirt, but it also wasn't sopping wet. Weird. I hit the stretch of Pipe Line towards 24, then the rest of Hemlock Road, across a little stream, to the road, back across the little stream, into the little stream (oops), and then I turned left to finish out the Pipe Line, which was slippery and muddy and wet (and stinky?). In my insanity, I started to conjure up a silly route called the "Pipe Line Traverse," which would either require extensive backtracking to avoid 24/93 or painful road walks.

Thankfully, life got better after the Pipe Line was done. I turned to hike near the AMC Camps and then onto Randolph Path, hitting two spurs I needed, then I returned across the horse bridge and back onto Meadow Road. I watched a little red squirrel chase a massive grey squirrel, which brought joy, almost got run over by a mountain biker, and then was back at my car! 

Now I only have four little and one medium section left: the Field Path area, the Brookwood Farm area, the Blue Hills Reservoir, the Braintree Triangle, and of course, the Quincy Quarries. Almost there!

Step-by-Step

- Park at Donovan Elementary School and start hike by entering woods and turning left onto Meadow Road.

- At Reed St., turn right onto unmapped path.

- At terminus, turn left onto path.

- At Reed St., turn around.

- At jct., turn left onto Ladybug Trail.

- At someone's back yard, turn around.

- At jct., turn left.

- At terminus, continue left onto Meadow Road.

- Hike network of trails with Sumner Path, Coolidge Path, Cranberry Circle, etc., then continue left on Meadow Road.

- At 5414, turn right onto Pasture Road.

- At 5424, turn right.

- At terminus, turn left.

- Follow to Pasture Road, then turn right.

- At turn, continue left onto Pasture Road, now a footpath.

- At 5440, turn around.

- At jct., turn left.

- At jct. at ballfield, turn right.

- At jct., turn right.

- At terminus, turn left onto Pasture Road.

- At 5423, turn right onto Pequimmit Trail.

- At 5421, turn left onto Pipe Line.

- Hike triangle at 5413, then turn onto Wannamanhut Path.

- At 5422, turn left onto Middle Road.

- At break in fence turn around, cross Pipe Line, and continue onto Middle Road.

- Cross Middle Street, continue onto unmapped foot path.

- At terminus, turn left onto Smith Trail.

- At terminus, turn around.

- At 5425, turn right onto Pipe Line.

- At terminus, turn around.

- At 5413, continue straight on Pipe Line.

- At MA-24, turn around.

- At 5413, turn left onto Randolph Path.

- Before 5401, hike large triangle at Vose Path, then continue south on Hemlock Road.

- At 5395, turn left onto Pipe Line.

- At terminus, turn around.

- At 5395, turn left onto Hemlock Road.

- At terminus, turn around.

- At 5395, turn left onto Pipe Line.

- At 5355, turn right onto Swamp Path (green).

- At 5360, turn right onto Randolph Path.

- At jct., hit spur to Ponkapoag Path, then continue.

- At 5401, turn left onto Hemlock Road.

- At 5362, turn around.

- At 5401, turn left onto Randolph Path.

- At 5413, veer right onto Meadow Road.

- Follow Meadow Road to car.

Blue Hills Reservation Map

Photo Album

Crystal Spring Loop, Doleful Pond, Healthy Heart Loop (Middlesex Fells Reservation)

Crystal Spring Loop, Doleful Pond, Healthy Heart Loop (Middlesex Fells Reservation)

Hike Type: Loop w/ spur, Loop, Little Loop

Distance: 5.09 miles

Elevation: 361 feet

Time: 1 hour, 43 minutes

Parking: Ample parking at Greenwood Park in Stoneham.
Hiking Challenges: 52 Hike Challenge 2026; Middlesex Fells Reservation

The Hike 

I foolishly thought yesterday was hot. Today was HOT. 80 degrees! I was killing time while Christien was at work, so I fugred I'd get the trails in the Crystal Spring/Doleful Pond area of the Fells for the first time. Plan was loosely a double loop, first following the red Crystal Spring blazes and second following the green Healthy Heart trail.

The hike started through a really cute loosely zoo-themed playground and then I started to follow the red loop around! The trail passed a meadow restoration area and then followed a small little boardwalk around a swampy area that's drying up. I then broke my plan of following red blazes and hit the spur trail to Doleful Pond, since it was a one-way trail anyway. I was loving how green everything was, but not obsessed with the bugs or being able to feel the pollen. 

At Gate 46, there was a backyard with dozens and dozens of birdhouses. I turned around and hiked to Gate 45, and enjoyed my time along the pond, which was more or less a murky pond that was 50% tall reeds. I did see a great blue heron flying away! There was a viewpoint that had two old stadium seats, which I found interesting. 

Dolefiul Pond Road paralled a stone wall, turned right, and then followed people's back yard fences to the gate. This was a nice side trip! Now, back on task.

There was a nice breeze and I was SWEATY from the hot sun. Back on the Crystal Spring Trail, I climbed up Whip Hill on a more trail-like trail as the treetops were clanking in the breeze. Near the top of the hill, there was a sign discussing rogue trails and what students at Stoneham High School are doing to help, which was cool. I passed a few people, but soon remembered that hikers are NOT nearly as friendly here as they are in the Blue Hills. Thinking about it, I think it's partly because this side of the city runs more metropolitan, and also more people are here for "walking" versus "hiking."

After Whip Hill, the Crystal Spring trail descended slowly all the way to Crystal Spring, which had some cool stone structures and many flowers, including the common blue violet. There was no water flowing, but still cool to see! The trail climbed after this and turns right near the height of land. The forest floor here is dotted with common mayflowers pre-budding, which was really pretty. 

Afterwards, the trail began to gradually climb up Saddleback Hill, which soon had a nice view over the road and to Spot Pond Reservoir. The wind was whipping! Afterwards, there were a couple more partial viewpoints, and then I was back at the playground!

I walked through the playground, which was more full of children this time around, probably because school was out. I started to follow the green blazes for Loop #2, but did hit the extra spur of Whip Hill Road before continuing on. The green blazes brought me around a wetland area and later made a few crossings with the Crystal Spring Trail. It circled an impressive boulder on the far side of the loop, and once near Saddleback Hill I checked the map and managed to get a stick in the eye... ugh...

Anyway, I soon finished that loop, and now it was time to just wander! I turned right at E2-2, hiked in towards some trails I hadn't hiked yet, past a wildly unphased deer, and then got the text that Christien was heading out, so it was time for me to head out, too!

Step-by-Step

Loop #1

- Park at Greenwood Park

- Start hike on red-blazed Crystal Springs Trail, clockwise.

- At E1-2, turn left. 

- At E1-1, turn right onto Doleful Pond Road.

- At Gate 46, turn around.

- At Gate 45, turn around.

- At E1-1, turn right.

- At E1-2, turn left onto Crystal Springs Trail.

- Follow Crystal Springs Trail clockwise, hiking spur to Pond Street, then continuing.

- At E2-3, turn left onto trail.

- At Woodland Road, turn around.

- At E2-3, turn left onto trail.

Loop #2

- Back at Greenwood Park, start hike at same spot, following green Healthy Heart blazes.

- At E2-1, turn left onto Whip Hill Road

- At "NO TRESPASSING," turn around and follow green blazes clockwise. 

- At E2-6, turn left.

- At E2-5, turn around.

- At E2-5, turn left.

Loop #3

- At E2-2, turn right.

- At E2-7, turn right.

- At E2-8, turn left.

- At F2-2, turn around.

- At E2-8, turn right onto Whip Hill Road.

- At E2-1, turn left and return to car.

Middlesex Fells Reservation Map

Photo Album

Hillside Pond, Valley Path, Unquity Path (Blue Hills Reservation)

Hillside Pond, Valley Path, Unquity Path (Blue Hills Reservation)

Hike Type: Loopty Loops w/ Long Spur

Distance: 5.00 miles

Elevation: 413 feet

Time: 1 hour, 42 minutes

Parking: Parking on the side of Hillside Street on Hillside Pond side.
Hiking Challenges: 52 Hike Challenge 2026; Trail Trace the Blue Hills

The Hike 

It's definitely May. I was hiking in chilly mist yesterday, cold rain on Saturday, but today it's a HOT 75 degrees out! Back at the Blue Hills, the plan was to hike the Hillside Pond, Valley Path, and Unquity Path areas today. I started with the loop around Hillside Pond, which really is a lovely little loop. There were unfortunately small bugs out. There were fortunately turtles out, too! The path around the pond is always surprisingly rugged, and I like it. I did get a bug in my ear, though.

I was surprised by how clear the water in the pond was. I was equally surprised by the wild amount of water bugs that were swimming and scattering about. They were also comically clumsy. They acted like cartoon characters when startled: the just swamp into each other, bouncing off one another until they got away from the shore line. I was cooking in the sun, so I was happy that I wasn't doing an overly strenuous hike. 

I took an unmapped STEEP trail to hit the rest of the trails, and to mix things up I did some loopty loops, crossing Chickatawbut Road to avoid having to turn around - I liked it! I also loved the old stone walls in this area. I also did not love the multiple enormous piles of horse poop? The gnats were really out and about, as was the pollen. I did my loopty loops and continue on the Barre Trail past a great broken boulder and then I continued on down to Border Path, which is truly a delightful stretch of trail. It easily descends alongside a small stream, crossing it at the low point. The skunk cabbages were looking luscious as the treetops began to gain color. 

I continued up Valley Path and was delighted to see that I got the longer trail that goes through the Bermuda Triangle. I hit the small connector to Valley Path, the lower of the two had a massive blowdown to navigate. I hiked back down Valley Path, spooked a family of four deer (only three alerted their tails, though!), and then continued along the Border Path.

I passed the private land and fence gate with no connecting fense, and then hiked the border path to Unquity Road before continuing onto the Unquity Path. This stretch of the hike was expected feeling much longer than the rest... because it was. Part of the path was nearly overtaken with Japense Barberries, the swamp area was stinky, and the coniferous areas were beautiful with giant pinecones on the ground. 

Back "above ground," I was gateful that the grass wasn't too long yet, but I was sad the cars on Unquity Road were too loud for my Merlin Bird ID app to work well. I did decide to play Pokemon Go on the return trip, which was my saving grace! The return trip took me exactly 25 minutes of Pokemon Go. Time to head to Costco for chicken!

Step-by-Step

- Park at Hillside Pond.

- Start hike with a counter clockwise loop around Hillside Pond, hiking the second spur to the road.

- At the close of the loop, take the unmarked steep gravelly path east.

- Follow path.

- At terminus, turn right onto Barre Trail.

- At jct., stay right onto path towards Dark Hollow.

- At jct., turn right onto path.

- At terminus, cross Chickatawbut Road.

- Continue onto Headquarters Path.

- At jct., turn sharply left onto Quincy Path.

- At 2112, turn left onto Dark Hollow Path.

- At terminus, cross Chickatawbut Road.

- Continue on path on other side of road.

- At jct., turn right onto Headquarters Path.

- Cross Chickatawbut Road, continue on Headquarters Path.

- At jct., turn right onto Quincy Path.

- At jct., turn right onto Barre Trail.

- Cross Chickatawbut Road, continue on Barre Trail.

- Cross Hillside Street, continue on Border Path.

- At 1224, turn left onto Valley Path.

- At terminus, cross Chickatawbut Road, continue on path.

- At terminus at Hillside Street, turn around.

- Hike left spur, then return to Valley Path.

- At 1224, turn left onto Border Path.

- At Unquity Road, turn around.

- At 1215, turn left ono Unquity Path.

- At terminus, turn around and return to car.

Blue Hills Reservation Map

Photo Album

Round Mountain, Mt. Frissell, Mt. Brace Loop (Mount Washington State Forest; Taconic State Park; Mount Riga State Park)

Round Mountain, Mt. Frissell, Mt. Brace Loop (Mount Washington State Forest; Taconic State Park; Mount Riga State Park)

Hike Type: Loop w/ Spurs

Distance: 5.78 miles

Elevation: 1,102 feet

Time: 2 hours, 10 minutes

Parking: Parking for 6 cars at the end of East St. (3 on each side of road), more parking on CT side.
Hiking Challenges: Taconic 12er, Operation Alaska Benchmark Challenge

The Hike 

...AND we're right back to it! I had a short stop at my car after my Bear Mountain Loop, and now I was planning an out-and-back over Mt. Frissell to Mt. Brace and back. I saw on AllTrails there was maybe a loop option that's not on the official map from the Round-Frissell col back to the trailhead, so I planned to check that out.

[10:16am - Mt. Frissell Trail]

My hike started on the Mt. Frissell Trail, blazed in red. The trailhead sign said 1.0 miles to Mt. Frissell, 1.5 miles to Ashley Hill Trail jct., and 1.8 to the South Taconic Trail. To no surprise, the hike started on a flat old road an a vast sea of, you guessed it, mountain laurel! At least the trail was wide now, I don't think I could have emotionally handled another leg-drenching narrow trail.

I hiked past the loop trail in question that I saw on AllTrails and it was clearly closed and in the process of being taken back over by vegetation - that option was out! The trail turned at this phantom junction and began to easily rise with tree views toward Round Mountain. I could hear people ahead of me, but I did not see them. I came up to a little scrambly section that was steep but fun! I wasn't thrilled that I'd have to come down this, but it was nowhere near as bad as Bear Mountain's scrambles.

There was a brief reprive followed by another steep scramble, which kind of kept steeply climbing until the top. I started to catch up to the voices ahead and could see some nearby peaks from the top of a few of the scrambles. There were some COLD wind gusts that I wasn't ready for!

[10:34am - Mt. Frissell Trail/Round Mountain Summit]

I was almost caught up to the group ahead of me, which was seven-ish people strong, at the top of Round Mountain, which had very nice views to Mt. Frissell on one side and Bear Mountain on the other. This area reminded me a lot of the Wyanokies in New Jersey. There was a brief open plateau walk on Round Mountain before it descended to the col. I caught up to the big group here, and it took me at least 6 "hey mind if I squeeze past you?" to finally get past all of them. At least one guy complimented my hot dog shirt?

Naturally, once I got past all of them I rolled my ankle pretty painfully, but nothing too bad. I saw a little pond off-trail on the right in the Round-Frissell Col and I could hear a grouse thumping while I answered nature's call. The climb up Frissell was similarly steep, but now slabby too, and my watch was being rude about my heart rate (telling me I was at 100bpm when I was closer to 170bpm, ridiculous!). I pushed to the top and hit a very very short spur to the true summit!

[10:49am - Mt. Frissell Trail/Mt. Frissell Summit]

The summit was marked by a busted cairn (I think) and a Summit Reigster. I didn't open it because it was (to no surprise) misting again), but yay! One more peak to go! I was still lamenting about coming down the slabs and scrambles, but we do what we have to do.

The Mt. Frissell Trail descended with rocky footing on sharp rocks, similar to the Kittatinnies in New Jersey, soon opening to what I'm sure would be a wonderful view out into the Hudson Valley and the Catskills, but today it was just more clouds! After a few minutes, I made it to the MA/CT state line!

[10:55am - Mt. Frissell Trail/CT State High Point]

The State Line also doubled as Connecticut's High Point. Writing this now, I do find it fun that I hiked both Connecticut's highest peak (Bear Mountain) and Connecticuts highest point in teh same day. The area was marked by a survey disc with a comically tall pole sticking out of the middle and what looked like another register box (it should also be noted that the Mt. Frissell Trail goes between MA and CT before this point). 

After this point, the trail narrowed and became scratchier and began to descend again over a few tricky wet slabs, bringing me back into the land of mountain laurel. 

[11:03am - Mt. Frissell Trail/Tri-State Monument]

I then came to the Tri-State Monument, which interestingly enough marks the point where MA, NY, and CT meet, but only says MA and NY (the same style monument as at the MA/CT line at the trailhead parking. There was an older piece of broken marble, maybe that used to say CT? A mystery! I ran into the first human in a while just afterwards, and then I was at the other end of the Ashley Hill Trail!

[11:06am - Mt. Frissell Trail/Ashley Hill Trail]

It was fun to see both ends of this trail, it felt like my hike up Alander Mountain was forever ago! The Mt. Frissell Trail continued ahead, the Ashley Hill Trail continued right, and an unblazed herd path to presumably nowhere traveled left, which was labeled "other way ->" in pencil.

Again, the trail narrowed and began to easily rise. I was finding this hike to be mentally a lot longer than it actually was, probably because I was approaching 10 miles in the day, even though this hike was still under two miles. The Mt. Frissell Trail turned a corner, passed a pond on the right, and then came to the South Taconic Trail.

[11:15am - South Taconic Trail (North)]

[11:19am - South Taconic Trail (South)]

There were finally good views! The South Taconic Trail/Mt. Frissell Trail junction had a wonderful view down to the farmland below with a glimpse at a few Catskill slopes beneath the clouds. I was curious about the pond, so I followed the South Taconic Trail northbound to see if I could get a better view. Turns out 1) I was not on the South Taconic Trail, just an old road that parallels it, and 2) there was now view of the pond. I came to the spot where the South Taconic Trail turned off of the road bed and turned around there, now actually following the blazes and enjoying the beautiful views.

[11:24am - South Taconic Trail/Mt. Frissell Trail]

[11:27am - South Taconic Trail/Mt. Brace Trail]

I was mentally gearing up for the climb up Mt. Brace, which looked not-too-far but not-too-close. I could see some flag and structure up top, which felt exciting! My hip belt continued to keep popping off, which was very frustrating, but thankfully the hike up Mt. Brace was pretty gentle. I came to an unmarked junction with the unblazed Mt. Brace Trail. Naturally, my brain started thinking about turning it into a loop hike, but that would add at least a mile and I was nervous not knowing how that trail would be. Later problem!

[11:30am - South Taconic Trail Mt. Brace Summit]

I crossed paths with a duo just before the summit, which appeared before I even knew it! The climb was actually delightfully easy, and the top was neat! The structure was a massive rock cairn with a wind catcher on a flag pole. The summit was motly meadowed with flagging tape all about (curious about that). I loved seeing Bear Mountain, Mt. Frissell, and even Alander Mountain! It was chilly and I was tired, so I of course didn't stay long. I think I might go for the loop?

[11:35am - Mt. Brace Trail]

I descended off the summit, and decided to do it! The grade looked easy the whole way, and time-wise it would probably be the same because I'd have to go slow over the scrambles down Frissell and Round. I also didn't want to see the group of seven again... Here goes nothing!

I did see the humor in that by making this a loop, and turning Bear Mountain into a loop, I effectively added mileage to my day and was essentially doing the originally planned hike, but I didn't care! The air was starting to warm up as the skies CONTINUED to drizzle. The trail was one big long old road with loose rocks and occasional streams. The wet part of the upper trail eventually drained into and crossed a real stream, and was better afterwards with wonderful flat dirt.

I then saw a red eft, took a bunch of photos, and offically killed my phone battery. Tragic! I started hiking even faster, just grateful that I knew where I was going. I also dropped my phone immeaditely after it died, scratching the screen protector.

I caught up to a trio in a very wet, flat spot, as they were admiring frog eggs. The trail continued to descend, getting progressively wetter and wetter, which kind of sucked. It reached a low point, crossed a bridge, and climbed up through more wet trail. Eventually, it flattened out and dried out, which led to the gate onto Mt. Washington Road!

[12:06pm - Mt. Washington Road]

[12:22pm - Mt. Washington Road/Bear Mtn. Road]

There were a bunch of signs for the Mt. Riga Corp. Inc. on Mt. Washington Road, basically saying "stay off of our land." It also made it seem like some people may reside on land owned by the corporation? It's very hard to find info on it online. Thankfully, the road was in great shape and I was able to truly cruise! The walk to the Bear Mtn. Road junction was longer than I thought, but the Bear Mtn. Road junction to the car was significantly and wonderfully shorter than I thought!

[12:28pm - End of Hike]

Naturally, I ended my hike with blue skies and a shining sun. Either way, it was a fun day of exploring this little corner of Massachusetts. It was fun to hit the CT high point, and hike in three states in a day! I've also now finished the Taconic 12er peaks outside of Vermont - yay! I had a nice long drive home, and then off to the Belknaps with Christien tomorrow!

One fun thing that happened on my drive home - a Mercedes SUV from New Jersey was weaving in and out of lanes on I-90 (there were people on the road, but all driving at highway speeds) WITHOUT using a blinker. Five minutes later, I saw that same car pulled over getting a ticket. Karma!

Step-by-Step

- Start hike on Mt. Frissell Trail.

- Near summit, turn right onto summit spur.

- At summit, turn around.

- At jct., turn right onto Mt. Frissell Trail.

- At jct. with Ashley Hill Trail, continue straight on Mt. Frissell Trail.

- At terminus, do a quick loop northbound on the South Taconic Trail, then hike south towards Mt. Brace.

- At summit of Mt. Brace, turn around.

- At jct., turn right onto Mt. Brace Trail.

- At terminus, turn left onto Mt. Washington Road.

- Follow Mt. Washington Road to car.

Map of Mount Washington State Forest

Photo Album

Alander Mountain via Alander Mountain Trail (Mount Washington State Forest)

Alander Mountain via Alander Mountain Trail (Mount Washington State Forest)

Hike Type: Out-and-Back

Distance: 5.95 miles

Elevation: 1,194 feet

Time: 2 hours, 2 minutes

Parking: Parking at Mount Washington State Park Headquarters for many cars.
Hiking Challenges: Taconic 12er, Operation Alaska Benchmark Challenge, 52 Hike Challenge 2026

The Hike 

I had the day all to myself and it was flirting with being kind of nice out with a bit of residual rain first thing in the morning. I had my sights on the four southern Taconic peaks on the Taconic 12er Challenge: Alander Mountain, Mt. Frissell, Mt. Brace, and Bear Mountain. Planning looked like I could do these in two hikes, and the trailheads were just a few minutes apart! I set a comical 3:00am alarm and was out the door at 3:20am. It was naturally pouring on my drive, but I was staying optimistic! The further west I drove the drier the roads became, thankfully. Originally it said 8:00am would be the end of the rain, but as I got closer it got bumped up to 7:00am - yay! I needed gas once I got off the pike and was horrified to see that it was averaging $4.50/gallon in the Berkshires, but I eventually found one for $4.20... ugh. 

I made my way towards Mt. Washington State Forest and East Street was down to a one-lane road in two sections due to road work, but since it was so early there was no one else out. I passed four deer and two turkeys living harmoniously on the side of the road, and eventually made it to the parking area at the State Forest Headquarters - with a porta potty! My stomach had been in a bad mood (I got a half and half pizza from Bertucci's last night and had two slices of Verde and two slices of Nolio for dinner and brought the other four slices for today, but I think the Nolio is now on my "treats my body like ricotta cheese does" list). I had my breakfast pizza, used the porta potty, which was in pretty good condition, and got started on adventure #1!

[6:25am - Alander Mountain Trail]

It was a brisk 41 degrees out with a few residual raindrops, but peeks of blue skies! There were endless birds singing, including a rooster (Merlin said White-throated Sparrows, Northern Flickers, Hairy Woodpeckers, Chipping Sparrows, Black-capped Chickadees, and Common Ravens). I was back with my orange 32-liter pack (versus my blue 40-liter pack) for spring - I did a little hiking pack restock last night for the warmer seasons. The Alander Mountain Trail started right at the parking area and traversed a nice, open meadow and is marked with blue blazes. 

Following the meadow, the trail entered the woods on a wide, well-blazed trail that felt like an old road. The trail turned left at a closed section of trail (but recently mowed) at another meadow and then crossed a stream on a bridge at another unmapped intersection. The trail had been averaging flat with minor easy ups and downs so far. Footing got a little muddier after the bridge, but nothing was too bad so far!

[6:35am - Alander Mountain Trail/Charcoal Pit Trail]

I soon passed the junction with the Charcoal Pit Trail, which did not look appetizing to me. It looked wildly wet, muddy, and grassy. I did have a couple option to extend this into a loop hike, but now I have eliminated one option! The Alander Mountain Trail crossed another stream and then came to the junction with the Ashley Hill Trail, which looked to be another wide road.

[6:38am - Alander Mountain Trail/Ashley Hill Trail]

I would keep this one in mind for my return trip if I was feeling inspired to extend my hike! I took my fleece off here, but kept my Frogg Togg jacket on as the rain had mostly stopped, but the leftovers from treetops were still falling. Off-trail, I saw a little herd path to a nice waterfall that was only a little sketchy to descend to - it was so pretty!

The Alander Mountain Trail descended for a minute to an area where two brooks meet - Lee Pond Brook, which had the waterfall from before, and the Ashley Hill Brook. I crossed over Ashley Hill Brook on a nice, large bridge and enjoyed the beautiful area. The water was so beautifully clear! There were also old stone foundations, maybe an old dam or mill?

The trail began to gently rise from this point, so I officially took my rain jacket off. Higher up, the trail entered the clouds (bummer) and passed a sign indicating the campground was a half mile away. There were a few cars from Connecticut at the trailhead, I wonder if they were camping?

After the sign, the trail flattened out in a really pretty area of open woods and young spring greens dotting the floor. The clouds were really trying to burn off, but without much success. I climbed a little steeper (but not steeply) to the junction with the Campground Trail.

[6:58am - Alander Mountain Trail/Campground Trail]

I pinned the Campground Trail for a possible return loop, as it links up with the Ashley Mountain Trail later on. The birds were back singing as I descended gently after the junction (I kept singing "the birds are back" to the tune "the boys are back" from High School Musical 3) before crossing a flat wet spot that led to a mountain laurel grove.

The climb officially-officially began when the trail momentarily became a literal stream. I kept thinking about how pretty it would be when the mountain laurel is in bloom! A massive bumblebee zoomed past me as the trail began to parallel a stream in a really lovely conifer grove. There was a metal sign with "last water in dry season" "written" via pinholes, and then the trail opened up again on a now rocky and eroded footbed.

The trail entered a very confusing wet, eroded area just after - some bird was trying to tell me which way was correct, but it wasn't overly helpful. Higher up, I re-entered the clouds as the trail steeply climbed up to the ridge. To my surprise, I came to a building!

[7:23am - Alander Mountain Trail/Watchmen's Cabin]

The building was the Alander Fire Watchmen's Cabin, thankfully indicated by a sign. It looked like the door could be opened, but I have a firm policy of not f-ing around to find out what creepy things may be lurking inside. The sign read:

"Historic Structure

Alander Fire Watchmen's Cabin

c. 1920's

Please respect this historic structure!

Alander Mountain Fire Tower, 1928-30 and associated Fire watchmen's Cabin at Mount Washington State Forest. The former site of this tower, located just tenths of a mile within Massachusetts from the state line, was managed by New York State froom 1928-1930. It was then dismantled and stored at Taconic State Park. In 1933 the tower was again erected on Washburn Mountain in Copake Falls, NY. Moved once more in 1963-64 to Beebe Hill, where it stands today.

Although the fire tower is gone form the original site on Alander Mountain, the 4 concrete footings remain. Also, this original Watchman's Cabin is actively used as a campsite for the Mount Washington State Forest.

Please be respectful, carry out all trash, and be diligent about your fires!"

There was a short, steep, ledgy push just after the cabin, which led to the terminus of the Alander Mountain Trail! I turned left onto the South Taconic Trail, which would lead to the summit of Alander Mountain.

[7:25am - South Taconic Trail]

This South Taconic Trail was fully socked in, but a beautiful short walk! It had tall bushes lining much of the stretch and puddles on the trailbed, kind of like Buck Hill in the Blue Hills, but I could tell there would be some nice views if I weren't in a cloud. 

[7:27am - Alander Mountain Summit]

And just like that, I was at the summit of Alander Mountain! The true summit is marked with old fire tower footings, an USGS marker, and a summit sign that was off on a tree slightly in the woods. I didn't stand here for long, in part because the only view was of the cloud I was residing in, but it was also damp and cold up here with a breeze. Plus, I had more hiking to do! I took a swig of Nuun and started my trip back to the Alander Mountain Trail and back to the car, still unsure if I was going to do a loop or not.

[7:33am - Alander Mountain Trail]

I wiggled down to the cabin and started... well, attempted to blast off back to the car! I made it to the top in one hour and one minute, I wondered if I could match it, or be faster on the return... I was also noticing I was two minutes ahead of the schedule I set for myself for the day - yay!

Back in the woods, the clouds were visibly higher up and if I stuck around for maybe 30 more minutes I would have caught a view, but oh well! I had work to do! I had been noticing all day the hip belt on my pack was feeling weird, and I learned why on the way down - the bottom tooth on the main buckle snapped off at some point in the past! That also explained why it unbuckled a few times. Bummer.

My toe got a little wet in the wet, eroded section, and I was moving slower than I wanted because of the water and footing, but overall it was good-going. 

[7:57am - Alander Mountain Trail/Campground Trail]

I decided to not do a loop at the Campground Trail junction since I had another hike to do just after this one. It smelled like a pine candle after the campground junction, and to my delight I saw some of the first red trillium of the season! I noticed first the three leaves, and then the droopy flowers! No pink lady slippers, though... There were also some droopy purple flowers in the area.

I was still impressively gassy throughout most of this hike, and it was really giving me a boost on this descent. I could start to hear the Ashley Hill Brook and soon made it back to the low point of the trail where the two brooks met. I crossed the bridge and started huffing it back uphill, which I was really cranky about, but it was also literally fine. 

[8:14am - Alander Mountain Trail/Ashley Hill Trail]

[8:17am - Alander Mountain Trail/Charcoal Pit Trail]

I hiked past the Ashley Hill and Charcoal Pit Trails through some wonderful rambling pine forests, passed the second meadow, rambled some more, and then finally entered the trailhead meadow. I didn't see a single human on this hike, and even with the wet trails, it was an absolute delight! I'd love to come back sometime to see the view, or even flirt with hiking the South Taconic Trail in it's whole (EDIT: wait of course that's what I want to do, it's only 14 miles).

[8:57am - End of Hike]

Back at the trailhead, I used the porta potty once more for good measure, changed into another set of dry hiking clothes, had my second two slices of pizza, and started my trek down to the MA/CT state line at the Mt. Frissell Trailhead!

Step-by-Step

- Start hike on Alander Mountain Trail.

- At terminus, turn left onto South Taconic Trail.

- At summit, turn around.

- At jct., turn right onto Alander Mountain Trail.

- Return to car.

Map of Mount Washington State Forest

Photo Album