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

Round Hill via School Mountain Road (Fahnestock State Park)

Round Hill via School Mountain Road (Fahnestock State Park)

Hike Type: Lollipop Loop

Distance: 4.61 miles

Elevation: 712 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hours, 39 minutes

Parking: Plenty roadside parking at School Mountain Trail trailhead.
Hiking Challenges: 52 Hike Challenge 2026, Downstate 28er

The Hike 

I was in New Jersey/PA for the weekend to celebrate my cousin's wedding and I wanted to find a stopping point on the way home to break up the drive. I could have done a Catskill High Peak, but I didn't want to go that far out of the way on a Sunday, and then I remembered the Downstate 28er list (which appears to be by the same folks who made the Taconic 12er!). I looked at the hikes that were furthest from Mom's house and landed on two in Fahnestock State Park. The plan was do to hike Round Hill and Candlewood Hill before launching myself back to Boston. I had a nice drive, a little over an hour long from our breakfast spot in Towaco to the School Mountain Road trailhead, which was a long dirt road with plenty of pull-offs and a parking lot (with a porta potty!) a bit further down. It was a humid, sunny 82 degrees when I arrived. I put on my new hiking clothes from Target (underwear that I feared was too short for my thighs, new 7" inseam shorts that I feared would be too soft and absorbent, and a new "active" shirt that I feared would be too heavy and absorbent. Starting off strong!

I started my hike on School Mountain Road, which was an old gated gravel road that was delightfully flat. I was planning to avoid bug spray for as long as possible, if that would be possible. I was excited to see that the trail markers were the Taconic Region ones, for no reason besides a little teehee. 

A minute or so into the hike, there was a kiosk with a map for the Hubbard Perkins Trail, which partly coincides with this and other trails in the park. There was a wonderful floral smell in this area. I soon caught up to a man and his off-leash dog at a sign that specifically detailed why it is important to leash your dogs... I passed him, gave a "how's it going," and got zero response. Yikes!

The School Mountain Road trail crossed over a couple lovely bridges and then I crossed paths with another duo. They were both friendly, and the one ahead shouted "oh shit John! Hurry! You can see a bass!" which made me giggle. The trail continued into the woods with a very easy gain, passing old stone walls and eventually crossing a larger bridge. Just after the bridge was the turn I would take for the blue-blazed Fahnestock Trail up to Round Hill!

Right around here, specifically at the 0.4 mile mark, 9 minutes into my hike, my camera battery died! I was incredibly displeased with this. I hate doing phone-photo hikes. I also just don't like being on my phone more than I need to on hikes, besides taking notes. And I only like taking notes becuase it helps me relive my hikes with more detail when I journal them, like this! Either way, I continued onto the Fahnestock Trail, turning sharply to follow the stream back toward the meadow and the bridges from before. There were a large number of dragonflies that had a teal/metallic thin body and black wings (a very specific google search looks like they were ebony jewelwings, also known as black winged damselflies).

The bugs started to increase, but I just kept my pace up, really avoiding the Deet. The trail stayed flat for a bit, eventually turning away from the water at another old stone wall. After the turn, the trail began to easily rise around the base of Round Hill.

As the vegetation increased, I eventually gave up and coated myself in bug spray, and it was a good thing I did! The trail became pretty overgrown and generally unpleasant to hike through. After rounding the corner, the trail began to start a moderate climb up the spine of the hill, switchbacking here and there with an overwhelming floral smell (which would have been lovely any other day, but not in the humid huff-and-puff). 

I hiked over what I'm pretty sure was a wild cockroach (?) as I was actively dripping pollen-soaked sweat. The baby blubes were taking shape, at least! There was a slightly overgrown view towards Bear Mountain, which was nice to see! I also passed a neat orchid-looking flower (a Goat's Rue, thank's Seek!). As the grassy climb continued, I found myself feeling less excited about getting in the car to get another hike in, so maybe I'll just extend this one? We'll see.

After rounding the shoulder of the hill, the trail worked through a pretty open-ish area that was ridiculously grassly (a la Harriman State Park's Long Path). I had to bug spray my upper thighs becuase the grass was so high. There were some tree views to the left as the trail crossed another old stone wall, and then I had to fight my way through a few thickets of raspberries (or blackberries, or wineberries... either way, thorns!). The grass got so thick at points that I couldn't even see my feet. I was not emotionally prepped for this hike.

I was quickly losing steam to extend the hike along the ridge, especially if this grass kept up. Naturally, after I had that thought, I crossed another stone wall and the grass became waist high. The trail slightly descended before the final climb up. I wrote: "I rarely actively hate a hike but this is really trying for it."

There was a short steep climb before hitting some more grass. Thankfully, the trail flattened at some blueberry bushes before turning for the final push. There were some obstructed views before a wonderful view, where I encountered my first person in a while, going in the opposite direction. 

The Fahnestock Trail rounded the height of land. I took a spur/herd path to the true summit, which was marked by a fire ring and a makeshift cairn. Back on the main trail, I noticed a view out to a nearby hill with a massive observation tower-looking thing. There was a WONDERFUL breeze here as I entered more and more grasslands. There were at least nice pink flowers (carolina roses, thank you, Seek!). 

The trail descended into a low point and then rose just a few feet to the junction with the green-blazed Round Hill Bypass, which I HAPPILY took. At this point, I was pretty sure I was just going to do this hike as-planned and call it a day. I was NOT in the mood and I was already overheated - I'm not ready for full summer. 

This trail was MUCH more enjoyable. It easily descended with rocky footing into a fern-filled wonderland, and I could see my feet the whole time! Further down, I crossed a stream with an adorable frog swimming about and then hiked over another stone wall.

The trail then entered a really pretty open forest with stone walls in every which direction and a vast carpet of green undergrowth (only a few inches tall, which was so much nicer than the multi-foot tall grasses from before. I could tell this used to be farmland clearly, but curious how long ago? The park was opened about 100 years ago. I was missing my camera - it was so pretty!

The trail then turned and rose above a mossy stream that would be absolutely stunning after a rainfall. There was a parent and child playing in the water. The Round Mountain Bypass trail terminated just a couple minutes later at another nice bridge!

The bridge was designed by the West Point Cadets Civil Engineering Class of 2021. I thought about adding a loop over East Mountain, but the trail looked similarly horribly grassy - no thanks! I was back on School Mountain Road and happily hiking back to the car.

I crossed another bridge, this time designed by the West Point Cadets Civil Engineering Class of 2020. I spooked a snake that I thankfully did not see and continued my romp along the beautiful road. I unfortunately was in a slightly negative headspace, so I was not able to fully enjoy the back end of this hike, but it really was lovely. There were seemingly endless stone walls throughout. 

The next bridge was a longer one with wooden steps to reach it, and it was also designed by the West Point Cadets Civil Engineering, this time the Class of 2019. I passed another sightless snake and enjoyed the tall trees lining this trail. After a bit of walking, I officially closed the lollipop and hiked over the final three bridges (I forgot to check if the design pattern continued, but the styles of the bridges sure did match!).

I soon made it back to my car and started to wipe the sweat (and pollen) off and change my clothes. Comically, I realized my backpack had been open the whole time! I did not have the energy in me to squeeze another possibly unpleasant hike in, so it was now time for a long drive back to Boston, naturally with a stop at Stewarts on the way!

Step-by-Step

- Start hike on School Mountain Road (white).

- At jct., turn sharply right onto Fahnestock Trail (blue).

- At jct., turn left onto Round Hill Bypass (green).

- At terminus, turn left onto School Mountain Road (white).

- Return to car.

Fahnestock State Park 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