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