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