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