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

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

Skyline Traverse Eastbound (Blue Hills Reservation)

Skyline Traverse Eastbound (Blue Hills Reservation)

Hike Type: Traverse

Distance: 8.51 miles

Elevation: 1,841 feet

Time: 4 hours, 14 minutes (3 hours, 53 minutes moving)
Parking: Drop Car #1 at Shea Memorial Rink in Quincy. Drive Car #2 and park at cul-de-sac at the end of Royall Street in Canton on side of road.

Hiking Challenges: Trail Trace the Blue Hills; Great Blue Hill Summits

The Hike 

Reunited with Sarah for a Skyline Traverse! I hadn't gotten a new patch in a while, nor have I done a traverse of the Skyline Trail in years, so it was time! We agreed to meet in Quincy at 7:30am and get started with our hike at 8:00am. It was nice and exciting to be getting a bigger hike in so close to home. I had plans around 1:00pm, so I was hoping to be back in time for that, we'll see!

[7:56am - Start of Hike]

We started on the access path toward the actual start of the Skyline Trail at 7:56am. It was a nice morning with blue skies, warm sun, a cooler temperatures in the high 40s/low 50s. At the terminus of the access path, we turned left onto the Skyline Trail, pretending that we weren't actually on the trail yet. I never understand why they have the trail start in such an awkward-to-get-to place. We hopped along the murky streams and litter-covered rocks, eventually OFFICIALLY starting our traverse!

[8:01am - Skyline Trail]

We hit the abandoned highway interchange, officially beginning our traverse! We retraced our steps and continued onward, missing the spur to Royall Street that I needed (oh well), crossing Green Street, climbing up and down Little Blue Hill, crossing paths with an... interesting fellow, and carefully crossing MA-138.

[8:26am - Skyline Trail/MA-138]

Thankfully the crossing wasn't too horrible. The steep climb up Great Blue Hill had both of us huffing and puffing, but thankfully the sunny views helped push us along higher up! We could clearly make out Mt. Wachusett from the view, which was a fun little treat, and we loved seeing the early springtime buds on the trees. 

We did take a side-path to the true summit to "boop" the plaque, and then we continued to the Eliot Tower, which gave us a wonderful view of Boston.

Our hike continued down Great Blue Hill, up and over Wolcott Hill, and then up and to the viewpoint on Hemenway Hill, which was just beautiful. It was nice to be on super-familiar trail, but more fun to be continuing on afterwards! We descended Hemenway and went up and over Hancock before making our way to Hillside Street.

[9:34am - Skyline Trail/Hillside Street]

The Hillside Street crossing was nice and easy and the walk up the Bugbee merge was lovely. We dipped off back fully into the woods and started our surprisingly heart-pounding climb up Tucker Hill (I always forget how rugged this side is, too). We scrambled down Tucker Hill, talking about what big hike we want to do next (maybe Lafayette tomorrow??), and then went up and over North Boyce before a final push up Buck Hill for a sit and snack. It was SO NICE out, but still a little chilly with a breeze. 

[10:32am - Skyline Trail/MA-28]

We got lucky with the timing of our MA-28 crossing and continued on into the woods, spotting an old orange blaze (which I love finding). We both took potty breaks in the flat stretch between the Pipe Line and Chickatawbut Hill - we were so joyful to be relatively alone in the woods - the perks of hiking on a Monday!

We steeply scrambled up Chickatawbut Hill, enjoying the view back towards Buck Hill, and then continued past Fenno, Kitchamakin, and enjoying the beautiful views of Boston and the ocean from Nahanton and the nicely laid stone steps all around.

We continued over the four and a half broken hills, admiring the beautiful forests in this area, alongside MANY Eastern Towhee birds and the old fenceposts. We were joined by a few hikers on the final broken hill, and easily descended to cross Chickatawbut Road.

[11:34am - Skyline Trail/Chickatawbut Road]

(EDIT: Writing this with time stamps, I'm really enjoying that we spent almost exactly an hour in each section of the park). Almost in the home stretch! We had a steep-but-short climb up Wampatuck Hill and enjoyed the partial views. We were both in-and-out of void time at this point of our hike, which wasn't a bad thing at all. We enjoyed the views into the little swampy pond after Wampatuck, and then had a STEEP, scrambly climb up to The Crags, which has one of my favorite unique views in the park.

We descended the Crags and went up and over the shoulder of Rattlesnake Hill, past Sullivan's Quarry, crossed Wampatuck Road, and had our final push across the St. Moritz Ponds and to Sarah's car! Yay! I was NOT making it to my 1:00pm plans, but we weren't TOO far off!

[12:10pm - End of Hike]

We got my car, got nice and changed, and locked in our plans to hike Mt. Lafayette tomorrow! We'd have a 4:00am departure time, meeting at the Burlington Mall to drop a car at 4:30 for the drive up. The weather was looking not-freezing, virtually wind-less, and CLOUD-FREE! Should be a great day!

Once home, I got showered, packed, and headed to Chrsitien's to see RAYE at the MGM Music Hall that night!

Step-by-Step

- Park at end of Royall Street and enter woods.

- At terminus of path, turn left onto Skyline Trail.

- At terminus/pavement, turn around.

- Follow Skyline Trail to eastern terminus at Shea Memorial Rink in Quincy.

Blue Hills Reservation Map

Photo Album

Sunrise Skyline Loop via Trailside Museum (Blue Hills Reservation)

Sunrise Skyline Loop via Trailside Museum (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.83 miles

Elevation: 1,214 feet

Time: 2 hours, 10 minutes (1 hour, 55 minutes moving)
Hiking Challenges: 52 Hike Challenge 2026; Great Blue Hill Summits

The Hike 

The original this weekend was to go up to Jay Peak where my roommate would take his first two ski lessons on his Indy: Learn to Turn pass, but due to a comically cold forecast (-40 windchills up at Jay), we opted to postpone, freeing up my weekend (we made the right call, as the mountain actually closed for the cold). I checked the forecast for the Boston area and it was going to be less riculously cold (low single digits) and clear skies, so I ended up decided to get a sunrise Skyline Loop in before the snow storm tomorrow. It was 5 degrees out without wind and I started hiking at 6:45am with only ski area workers in the parking lot.

My spikes were on and my puffy came off once at the Summit Road, where I could hear the groomers at the ski area. There was just enough snow and ice to warrant the spikes. I made it to the tower just as the sun broke over the clouds and horizon, which was truly perfect timing, as I couldn't stay for long due to the cold. I made my way over to the summit once the intense orange faded to a bright yellow, passed two people who were running(?!) the road and realized I forgot my Nalgene... bummer! There was naturally more snow up high than down low, but nothing too intense.

I made my way down Great Blue Hill, put my puffy back on, took it off after climbing Wolcott, and took my hat off after climbing Hemenway. It was breezier and colder on Hancock and my poor spikes took quite a beating on it, and I almost slide right down Hancock!

I crawled up Houghton trying not to sweat and I realized it might just be time to retire my spikes... It was breezier, colder, and shadier between Houghton and Great Blue Hill, the streams were still running, and the trees were making some scary sounds in the wind. I worked my way carefully up the headwall and back to the summit, arriving at the same time as another runner who said "son of a b****" once he landed which made me giggle. 

I made my way back over to the Eliot Path for my descent, and the breeze was now head-on, making for a COLD descent. Thankfully, this was the coldest I'd been for the whole hike, so I would be warm soon. This was overall a great hike, and the only real issue I had was that my cold-weather exercise-enduced asthma started to act up, but thankfully I found my inhaler!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, climb tower for sunrise, and then turn right onto Eliot Circle. 

- At trail jct. after crossing the Summit Road, turn left to summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, retrace steps to Eliot Path and to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (Blue Hills Reservation)

Skyline Loop via Trailside Museum (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.56 miles

Elevation: 1,191 feet

Time: 1 hour, 41 minutes
Hiking Challenges: 52 Hike Challenge 2026; Great Blue Hill Summits

The Hike 

Oof. I had a great start to my Tuesday morning followed by a very heavy and stressful phone call from my mother that more or less sent me into an emotional spiral that resulted in me leaving school early - not too great! The positive, I guess, is that it was actually a really beautiful January day - sunny in the low/mid 40s, so I took it upon myself to head back to the Blue Hills in an attempt to get my body regulated. 

Thankfully, the second I stepped outside, I knew I had made the right call. I started climbing up the Eliot Path, dodging little bits of residual ice. After the road, I skirted around the usual ice flows and enjoyed smelling the crisp, fresh air. I truly could have worn shorts it was so nice out - I had the Walmart sweatpants that I always wear with an REI wool shirt on top (the one that ALWAYS has my itching and chafing... I need to replace it with something new) and I was a bit sweaty.

I hit the summit and the connector trail was still closed, so I followed the gravel path down toward the Skyline Trail and followed it over to the Tower, which had a nice, slightly hazy view to the hills, the ocean, and Boston. A very pretty Blue Jay followed me for a bit, too.

I hiked past patches of needle ice and I descended Great Blue Hill and climbed Wolcott. There was no owl (I will forever be looking in that one spot) and eventually I passed a guy who was walking like 0.1 mph slower than I was. There were many blowdowns in a formerly burned area. I hiked through Downtown Crossing and climbed up Hemenway Hill and then down and back up again to Hancock.

The descent off Hancock was very wet, but manageable. I passed a well-behaved, leashed dog that looked like it was dragged out of hell (MASSIVE dog, German Sheperd-ish build, but had eyes dark as night - spookyt!) and made my way onto Hancock Street, where the horses were out! It's crazy to me how massive horses are, and it really does surprise my every time.

I had a shockingly strong climb up Houghton (I was NOT humbled) - I think partly because I was hiking slower than I had been and my pack wasn't weighed down, but I'll still take it! Both streams were running pleasantly, and I made it back up Great Blue Hill without much issue either (and dodged the ice flows at the headwall). I hit the summit again and then made my way down Eliot Path back to the car. I REALLY needed this hike.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, retrace steps to Eliot Path and to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: o-o Loop

Distance: 4.62 miles

Elevation: 1,191 feet

Time: 1 hour, 37 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

First hike in a minute! I hadn't been hiking much partially because this just happens in the fall with my schedule, but also because any time that I would hike during the week I've been going on dates - which I guess is a net positive, but I'm tired! This day was also Rosh Hashanah - I was supposed to hike Mt. Monadnock with a coworker, but she bailed (I wasn't surprised). Plus, it was raining up in New Hampshire. I ended up sleeping in and going for the Skyline lap. Sarah also texted me about doing a single day Pemi Loop? Is she crazy? (yes, she is, and now I can't stop thinking about it). It was a breezy 65 degrees! I had to pee at the parking lot already but there was a big group forming, so I blasted off. 

The smell of the woods brought me back to life right away - I missed it. I climbed up Eliot Path and crossed the road - I noticed some new graffiti in the little hollow before the road. It felt like a summer morning as I continued up to the summit of Great Blue Hills. There were trucks at the gravel path getting ready to do something with one of the communication towers. I continued up and over Wolcott Hill, where there was a wonderful breeze in Downtown Crossing. More wonderful breezes were to be felt on Hancock, and then I saw three horses at the stables on Hillside Street! They were in seperate enclosures as folks worked on the stables.

I was again humbled by Houghton, but also less humbled than usual. It was a little buggy between the two streams, and I passed the large group of parking lot people at the sharp turn just before the headwall push. I was fighting for air, but not totally gassed at that last climb, and had to lengthen my hike slightly due to the gravel path being closed for the communication tower work. I hit the top and descended via the ski trails - I am so excited for ski season.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to parking lot.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: o-o Loop

Distance: 4.45 miles

Elevation: 1,198 feet

Time: 1 hour, 31 minutes
Hiking Challenges: 52 Hike Challenge 2025; Great Blue Hill Summits

The Hike 

First after school hike of the year! I had a wonderfully easy drive, but I did smash my hand on my car door (to be clear, ON my car door, not in my car door), and it hurt... wildly bad? Hmm. It was a super nice day out - overcast at 72 degrees. The air felt dry in the parking lot, but got super humid halfway up - I'm guessing from the recent rain and the flatter area just holds water better. There were some early fall colors on the Eliot Path, but I'm pretty sure they were still just from the drought. I passed one guy who was moving slowly and he said "you'r elike a jet and I'm a single prop," which was very funny. I was also VERY sweaty. 

There were locked porta potties up top, which excited then disappointed me - I've always throught the top just needs porta potties and a water fountain! They're redoing the spur path to Skyline, so it is now closed. I had to descend via the gravel path closer to where the Skyline dips to MA-138. Along Eliot Circle, I noticed some sticks in the ground that read "edge trail" - which I assume meant that the sticks were marking where the eventual edge of the trail would be once work is done. 

On my way down Skyline North, the pines were smelling wonderfully. An older gentleman passed me while running in a polo and jeans as I noticed the blue blazes had been recently touched-up. I took a quick potty break on Hemenway and soon enough I was on Hillside Street - with my whole "trying to date again" thing going on, I have a LOT to think about!

I had my most successful Houghton Hill climb in a while (still flirted with death, but I was feeling stronger than usual). I think I felt so good because I hadn't hiked in a little bit and the horrible warm humidity of summer had finally subsided. Further down the trail, the streams were basically dry and there were a comical amount of mushrooms in that seasonally wet spot between the two streams. 

I also felt pretty strong going up the headwall back to Great Blue Hill, and I enjoyed the smell of wet dirt on my final push - it smelled like fall. I hit the summit and descended via Sonya, which had shockingly clear views from Wachusett, along the entire Wapack Range, and of course, Mt. Monadnock. 

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to parking lot.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: o-o Loop

Distance: 4.52 miles

Elevation: 1,201 feet

Time: 1 hour, 43 minutes
Hiking Challenges: 52 Hike Challenge 2025; Great Blue Hill Summits

The Hike 

I really wanted to drive up to the Whites to hike Mt. Wolf, but a late night compounded with another day of high anxiety, I opted to sleep in a bit and revisit the Blue Hills, which I was not mad about! I was only mad that I was still feeling anxious, but alas... I made it to the Trailside Museum parking area around 8:00am, which was a little busier than yesterday, but by no means full. The weather was yet again wonderful at 67 degrees with relatively dry air and a nice intermittent breeze. My body was feeling tired after yesterday's hike so I was planning to take things slower.

That plan did not last - once I got moving I truly sailed up the Eliot Path - my legs were feeling good! I made it up to the summit and looped around toward Eliot Tower, where I noticed a stone on the ground that read "BMB Take this with you. Do not leave it behind!" - I am incredibly curious what that could be about!

Descending along the Skyline Trail, I got stuck behind a bunch of guys in golf attire, but eventually got to pass them and made my way into Wildcat Notch, which smelled wonderfully floral. My watch had been misbehaving again, showing low heart rates when it should have read 160+, but it fixed itself once I was climbing up Hemenway Hill.

There was a slight traffic jam at the headwall at the Breakneck Ledge junction, but I scrambled up the side no problem. At the top of the scramble, I ran into a woman with three dogs who I saw yesterday - she recognized me! I got stuck behind another duo that wouldn't let me pass on Hancock, but soon I got past them and made it down. At the bottom, I took a swig of water and saw a family of three deer staring at me! They moved before I could get a good photo, but when I was getting water at the water fountain, there was a hummingbird at the headquarter's hummingbird feeder! That made up for the deer.

I was much sweatier than yesterday at this point, and I drank too much water before my Houghton climb, because I was feeling ROUGH. I also saw god, again. My heart rate got up to 187, which is high for me. I did survive, though, and then I got to zone out for the next bit of time. There were some bugs near the stream crossing between Houghton and Great Blue Hills, but nothing too bad.

Up next was the final push up Shadow Cliff back to the summit of Great Blue Hill. I think I did almost pass away, but I stopped right after the scramble to question my life choices and catch my breath. I opted to not take a victory lap today as I was nearing death, and instead to just enjoy my second summit and a nice walk down Sonya. I passed a guy peeing into the bushes on my descent, and when I got to my car, realized I, yet again, did not lock it. Oh well!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to parking lot.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya + Victory Lap) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya + Victory Lap) (Blue Hills Reservation)

Hike Type: Lollipop Loop-Loop

Distance: 5.79 miles

Elevation: 1,539 feet

Time: 2 hours, 10 minutes
Hiking Challenges: 52 Hike Challenge 2025; Great Blue Hill Summits

The Hike 

I am officially back in New England! I am sad to say goodbye to my Jersey Summer, but it is nice to be back and beginning to put my life back together. My body woke me up at 6:45am on my first morning back, so I decided to go to the Blue Hills. It was BEAUTIFUL out. 56 degrees (!!), blue skies, and not many people. I was going to breaking in a new pair of Merrel Moab 3s (the hiking shoes) and a new pair of Darn Tough socks. I put band-aids on my nipples after the pain from the past two hikes, I put my weighted water bottles back in my pack (just two out of the three), and off I went!

The new shoes were delightfully grippy on the usually slippery rocks along Eliot Path, and soon enough I was back on my favorite local hill! It was nice to be hiking on a trail-trail again, instead of the Tourne's gravel path. There was some new construction around the observatory which in turned closed the spur path to the Eliot Circle/Skyline Trail, so I had to follow the gravel path past the buildings to catch Eliot Circle further down, which I was not upset about.

The construction looks like they're redoing the sandy area at the base of the tallest communication tower and possibly doing some erosion control along the Eliot Circle. Closer to the tower, the Eliot Circle has been widened to a dirt road, I'm guessing for construction vehicles (and maybe to match the path on the other side of the circle). 

The view from the tower was delightful and I only shared it with a few others before descending along the Skyline Trail North. There were a suprising amount of rattling red squirrels in the trees as I crossed paths with a surprising amount of people. I also tightened my shoes, as they had gotten loose (the beauty of breaking in new ones!). 

This hike is definitely harder than the Tourne, but I am also grateful to have had the Tourne while in Jersey. I made it up and over Wolcott, Hemenway, and Hancock Hills and down to HQ, where I topped off my water bottle. I played some Pokemon while walking along Hillside Street and then shoved my way past a bunch of people standing and chatting on the Skyline South Entrance(??). I got Humbled By Houghton yet again (I came close to death, I fear), and began to cross paths with many folks I had already seen.

Somewhere in the sag between Big Blue and Houghton I realized that I, yet again, left my keys in my car! Why do I do this! Thankfully it was still just beautiful out. I also was lamenting that the nice weather was not here to stay - next week is Band Camp and highs are mid-90s all week. It will NOT be nice.

I eventually made it to the final climb up Great Blue Hill, and I think I truly saw god I came so close to death. I summited again and descended along Patriots and Sonya - both of which seem to have been patrially mowed in the past month. There were a suprising amount of people out on the ski slopes, which was kind of nice to see. I did have one dog charge at me, which was annoying, but it recalled once it started sprinting.

At the bottom, I was feeling strong and brave and decided to take a victory lap! There were a lot of people on Eliot Path now, but I wanted to get a third summit in, so I was a big boy and turned around at the parking lot. I was much more tired this time, but still moving strong (doing this also helped cool the anxiety I've been dealing with recently). I made it to the top and then descended along the ski trails again, where I was surprised to see a dad had set up a tent with his two toddlers and his dog? He was taking them on a nature scavenger hunt, which was actually really cool. I think the kids might have been a little young for any of it to have any impact, but good effort!

Soon enough I was back at the car and doing a stressful grocery shop before continuing to unpack my life from 6ish weeks in New Jersey!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to parking lot.

- Repeat Eliot Path - Eliot Circle - Patriots - Sonya loop for extra credit.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya; CCW)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.23 miles

Elevation: 1,181 feet

Time: 1 hours, 45 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

Same thing, different direction! I was feeling CRAZY and decided to hike my usual loop in the opposite direction! I had a sleepy drive and it was another hot, hazy, humid day at 85 degrees. To really make things exciting, I knocked my Nalgene off the top of my car and it EXPLODED. I swear, I am truly the only person capable of shattering Nalgenes. I decided I'd still go for the hike and bail if I got too hot/dehydrated, knowing that there is a water fountain at the halfway point.

I made it one minute into my hike before I was pouring sweat. I crossed paths with a trail runner who I had seen dozens of times before and soon enough I was up top at the summit. There was a guy working on the big antenna, which was fun to see. Descending Skyline South, I saw another one of those large spiders I saw yesterday! I could just make out the top of Buck Hill from a standing view before the steepest descent. It was kind of fun to be going in reverse - it felt like a whole new route!

The intermittent breeze truly saved my life throughout this hike. The water crossing near the cool rocks was basically dry and the other one was down to a trickle. Climbing up Houghton Hill, I noticed a really pretty red hue on many of the trees that isn't as noticeable from the other direction. There was an unfortunate amount of dog poo bags on Houghton, but also a pile of what I believe to be coyote poop, so that was exciting?

While descending Houghton, one of those big spiders LANDED on my arm, I smacked it, and it POPPED. Made a complete mess. It was horrible. I made my way down to Hillside Street and awkwardly walked past the line cars, ready to fully camel up at the water fountain. I also got to enjoy watching a groundhog investigate the stables!

I climbed up Hancock Hill, up and over Hemenway, and found myself missing the owl on Wolcott. The final climb up Big Blue was buggy and slow, but overall much easier than climbing up the other side. I think overall this was a much easier loop on the muscles, heart, and lungs, but the steeper descents killed my knees!

An EXCELLENT gust of wind hit me on Eliot Circle as I worked my way back to the top, again wishing they had a water fountain up top! My descent was wonderfully windy and I decided this would be my last Sonya until the fall when the grass begins to die - it has officially gotten too long for my liking (and for my phobia of ticks).

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.21 miles

Elevation: 1,171 feet

Time: 1 hours, 42 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

After a few days of getting caught up on sleep after my Californian bender, I was finally feeling back to normal. I made it to the Trailside Museum parking area after work in 82 degree, humid-but-breezy weather. The drive was slow, but I was excited to get some hiking in! I cruised up the Eliot Path, passing a couple sharing a joint on the way (I would see them later near the tower and one of them was NOT having fun). 

I continued from Great Blue Hill over to Hancock Hill on tired-feeling legs. I'm unsure if my legs have been feeling more tired becuase I have just been more tired, if the humidity is just taking its toll, or the third water bottle I added to my pack is just enough extra weight that I really feel it... Who knows!

I descended Hancock and climbed Houghton in one tank of gas, but it did NOT feel good! I also noticed an absurd amount of LARGE spiders on this hike (quarter-sized), and they were all the same type of spider but like a mile away from each other, hmmm. I noticed some dried out lady slippers as I hiked from Houghton to Great Blue Hill, where I also noticed the baby blueberries beginning to transition to blue! There was a wind after Shadow Cliff that I think saved my life since I was SOAKED. 

I noticed some daisies near the summit as I descended down to the ski area, which was surprisingly hazy. I played some pokemon as I descended and saw a red-tailed hawk fly away from a tree and let out its trademark "CAAAAAAWHHHHHHHH," which was pretty sweet.

Near the end of my descent, I noticed some foam-like substance on some of the grass at my feet. According to Seek, it was caused by a type of spittlebug. According to Wikipedia:

"The larvae are well known for the self-generated foam nests which can be observed during spring in meadows (especially on cuckoo flowers, Cardamine pratensis, and broom, Genista, species). The larvae in the foam nests are largely protected from predators and also get the necessary moisture for the appropriate development and temperature, so their mortaility remains low even in bad weather. The larval stage lasts about 50 days. The adults leave the foam nest only when it is completely dried. This takes about ten days. The females mate soon after.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.24 miles

Elevation: 1,175 feet

Time: 1 hours, 45 minutes
Hiking Challenges: 52 Hike Challenge, Great Blue Hill Summits

The Hike 

As is unfortunately a theme this spring, I had yet another angry, sleepy drive after school and simply needed to blow off some steam in the woods. It was a warm 83 degrees out with wildfire smoke in the air. The sky was white and the sun was orange, which was hauntingly pretty. There were an annoying amount of cars in the parking lot and I was already sweating while putting my shoes on - oof!

The climb up Eliot Path was buggy but visually beautiful due to the faux golden hour. The shade felt significantly cooler than the sun, which was helpful. There were unique, hazy views from Eliot Tower and I trailed a group of four women loudly talking about toenail health in front of me before finally letting me pass near Wildcat Notch. My legs felt wobbly as I climbed up Wolcott Hill and I finally caved and put on bug spray, which unfortunately did help.

I didn't see the famous owl, but I did hear some bullfrogs in the first col, and I soon made it up and over Hemenway and Hancock, too. My hips were still chafing slightly from my trip to Hibbard, Square Ledge, and Passaconaway, and I did stop to relieve my bladder on Hancocok.

At the reservation headquarters, I made use of the water fountain, which provided me with some wonderful, chilly water - thank goodness! I watched bugs drown in my sweat as I was getting humbled by Houghton Hill, and as per usual I zoned out from Houghton to the final climb up Big Blue. My legs were TIRED going up Shadow Cliff, and I found myself wishing for a water fountain up top after this climb. I ran into a bunch of bikers at the summit, which was also annoying (a theme today), but I had a wonderful descent down Patriots & Sonya. I also got to watch the ski area management setting up their new ice cream stand! I was not in the best headspace for this hike, but I am glad to have done it nonetheless.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Eliot Circle & Sonya)

Skyline Loop via Trailside Museum (w/ Eliot Circle & Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.83 miles

Elevation: 1,194 feet

Time: 2 hours, 24 minutes (2 hours, 13 minutes moving)
Hiking Challenges: Great Blue Hill Summits

The Hike 

AAAANNNNDNDDDD we're back! I had another brutal drive down, but any time in woods is better than no time in woods! It was 76 and a little hazy with a few clouds in the sky. Sarah and I planned to meet, but she was running 20ish minutes behind me and I had to PEE, so I decided I would get started before her, take care of my business, and then meet her at the top. I had to hike with no straps buckled on my pack my bladder was so full. I took care of business partyway up the Eliot Path and then continued to struggle my way up - I did my first "leg day" in about 6 weeks this morning, so my legs were FEELING it. 

I passed someone hiking down while smoking a cigarette, which was... interesting. Once on Eliot Circle, I took a "victory lap" around the loop to kill time before Sarah made it up. On the Eliot Circle, after the ski area spur trail, the black oaks were growing in quickly, making the trail a bit of a gentle car wash. Once I rounded the corner near the Skyline Trail I was gifted with a wonderous breeze. I then crossed paths with a guy in a full sweatsuit that was fully soaked, and then I climbed the tower and interruped a... happy couple?

I made my way around and to the summit, where I played some Pokemon Go while I waited for Sarah. Once she arrived, we were off! I told her I was going to be slow, and boy, was I correct!

We took turns ranting about our bosses from Big Blue to Hancock - made the time go super fast! We admired the pink lady slippers on the route, and then the harlequin flowers and blue toadflax on Hancock. We continued on Hillside Street and struggled up Houghton Hill (I think she was just pretending to be tired, she's so nice), and made our way back up Gerat Blue Hill. Mile 3 took 38 minutes, which might be a new slow record!

From the top, we descended along Patriots and Sonya to wrap up a slow, but rewarding hike.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- Hike full Eliot Circle loop.

- At jct. with Eliot Path, continue on Eliot Circle.

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.23 miles

Elevation: 1,178 feet

Time: 1 hours, 36 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

Back to school after Memorial Day Weekend and I had a HORRIBLE drive down to the Blue Hills (took over an hour and 10 minutes, which is ridiculous). There were many cars at the trailhead, but I was determined to persevere! It was a hot, but not opressive 83 degrees out with some bugs flying about, but I got right to work!

I was moving slower than usual but still at a good pace up Eliot Path. It was hazy overhead with some clouds, and I was blessed with catching a shiny Zigzagoon on Pokemon Go once at Eliot Circle! I summited Great Blue Hill and began my descent, where I passed a vibrant, massive Blue Jay. I wiggled through an unnaturally large amount of people in Wildcat Notch and climbed up Wolcott, which had a pretty juxtaposition of burned understory and new growth at the summit.

In the col, I sadly did not see the owl from a couple weeks ago, but I did see some harlequin flowers up on Hancock Hill! The blueberry bushes are starting to bloom, too. I descended to the sounds of many tweets and chirps and noticed a chunk of rock broke off at the bottom slab of the Hancock descent - I wonder if weather or human casued?

Hillside Street was wonderfully breezy but dreadfully stinky - a weird combination of swamp, horse, and cars. The flowers of the lesser periwinkle at the base of Skyline South were all gone, and the lower stretch of this climb was surprisingly muddy. I had added another water bottle to my pack just for some extra weight and my legs definitely were feeling it on the Houghton Climb, but I was greeted with another wonderful breeze once at the top.

I zoned out for a while until I was back on the summit of Great Blue Hill, where I descended the much narrower ski area spur path. The Summit-to-Circle stretch was pretty grown in but the Circle-to-Ski was still in good condition. I passed a brown bird with a red head and a pointed beak at the Patriots headwall (might have been a male Yellow-shafted Northern Flicker, but I'm not 100%). 

I was blessed with one more wonderful breeze once on Sonya, which had taller grass than last time, but was still manageable without getting any ticks. Overall, a nice afternoon! Now off to Costco for my weekly chicken!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album