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

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

Hike Type: Lollipop Loop

Distance: 5.00 miles

Elevation: 1,289 feet

My Time: 1 hour, 55 minutes

Book Time: 3 hours, 8 minutes
Hiking Challenges: 52 Hike Challenge 2026; Great Blue Hill Summits; Trail Trace the Blue Hills 2

The Hike 

So... this is a werid one. I got home to Boston last night after my hike up Vly and Bearpen and went to bed sometime around 10:00pm. I woke up around 6:00am to the scary text from Mom saying "call me." I called her, and she said there's no good way to say it, but my cousin was murdered last night. I don't think I took a breath for at least a full minute. Without diving too deeply into it, it was a kidnapping-murder-suicide by her ex-boyfriend, and it happened last night. Mom did call me last night, but I was already asleep. After talking to her for a WHILE, I sat down, and simply could not move. I started telling a few of my friends, but I didn't even know how I was feeling due to the shock. After a couple hours of sitting and occasional breathing, I decided to go to the Blue Hills (in hindsight, my body was simply in shock). 

It was a humid 75 degree morning and my mind was... confused. Murdered? I don't even know what to make of that. The parking lot was uncrowded and my body was a little tired from yesterday's hike, but not too badly. I was DRIPPING sweat once I got to Eliot Circle, but thankfully there was a spectacular breeze. 

Up top, there were some new picnic tables and some work being done at that beachy area behind the garage building. I worked my way around to the Skyline Loop, seemingly in-and-out of consciousness. The breeze brought me back again on Wolcott Hill, and there were a few blueberries left on Hemenway.

I decided to follow the Hancock Trail to catch some views and avoid people and try to make sense of what was happening in my brain. I navigated the braiding paths, got spooked by a snake, and enjoyed the view from the descent. The sun was noticeably hot coming down Hancock, and the Hancock Hill Path was quite lovely. At this point, everyone in the family had been notified, including my cousin who just had a baby.

I hiked past some blueberries, waved to the horses on Hillside Street, and had my ass handed to me on Houghton, more than usual. My heart rate got up to 185, which is higher than I like it to be! I was the kind of sweaty that turned my fingers pruney. The first stream crossing was simply a mud pit, and I passed some dogs free running through the woods? I later passed their humans who simply did not see worried. 

I made the climb up to Shadow Cliff, and then my body officially broke out of the shock it had been in and I just started sobbing. Not great. I worked my way up the trail, unclear if the moisure on my face was sweat or tears, and (this is funny I swear) then I crossed paths with a group of 12-15 hikers that were all so happy to be out and active. The kind of group that is 55+ and every single hiker will say hello to you as they pass. It's funny, I swear!

I made it back to the top and had on and off panic attacks on the hike down. Writing about this hike (admittedly much later than I meant to) is really crazy, and the next couple of weeks were going to be ROUGH.

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 Hancock Hill, turn left onto Hancock Trail.

- At jct., turn right onto Hancock Hill Path.

- At 1172, turn left onto Skyline Trail.

- 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, walk down Summit Road.

- At 1051, turn left onto Eliot Path.

- Follow Eliot Path to car.

Blue Hills Reservation Map

Photo Album