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: 4.54 miles

Elevation: 1,121 feet

Time: 1 hour, 40 minutes
Hiking Challenges: Great Blue Hill Summits; 52 Hike Challenge 2026

The Hike 

I was, to no surprise, not doing well. I had a couple of nice days with Christien as I processed/avoided thinking. I decided I'd to a Skyline Loop in preperation for a trip to the Whites tomorrow before heading to New Jersey to fly to Florida... It was a low-humidity 73 degrees out, though, which was wonderful. I noticed a little speck of mold on Nalgene, which is my #1 ick, but I persevered. 

I hiked up Eliot Path, hit the top, and continued around to start the loop. I passed a group on Eliot Circle and overheard one say "we're going to have some GOOD naps today." I stomed up and over Wolcott, Hemenway, and on my way up Hancock I passed a duo of teenage girls that said "I think deodorant is the LEAST of my problems." It's a good day for quotes!

Coming down Hancock Hill, I was ASTONISHED to run into a stoat/American ermine/short-tailed weasel (apparently all three are the same animal?). I watched it for a good five minutes - it was so cute and I was shocked to see it so close to Boston, in such a popular park, on such a popular trail! Let us be reminded that I was in a BAD headspace, so this stoat did in fact make me cry, and that is okay.

I was later Humbled by Houghton™, per usual, but not nearly as horribly as my last hike. The first stream crossing was somehow even drier than last time, and I passed the nap crew again.

I was similarly humbled going up to Shadow Cliff, but I did NOT cry - improvement! Back on Eliot Circle, I saw they were installing granite stairs at the former beach area. I made it to the top and descended to the ski area, which had a super clear view to Wachusett. There were plenty of flowers on Patriots, and I enjoyed the beautiful visibility the whole way down Sonya. I am so glad this hike was such a positive one, I needed it!

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