Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Hike Type: o-O Loop

Distance: 4.97 miles

Elevation: 1,220 feet

My Time: 1 hour, 46 minutes

Book Time: 3 hours, 5 minutes

Parking: Ample room at Trailside Museum
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Great Blue Hill Summits

The Hike 

Happy Pride Month! It was time to officially begin my second Trail Trace the Blue Hills Map! I had a dreadfully sleep drive with "heavier than usual traffic," landing at the Trailside Museum at 3:35. There were very few cars, which brought me joy! I was planning on just doing a fitness hike with a possible detour to get the full red-circle route for my new map, we'll see! It was sunny, 62 degrees, and there was a light breeze. It was lovely!

Somebody unfortuantely got started right before me, but I had to pull off to pee anyway. I eventually caught up and passed him and continued my way up. There were a bunch of leaves on the ground after Saturday's storm. My legs were in a weird mood, feeling a bit like a baby deer learning to walk. I couldn't really get a rhythm together on my climb. Thankfully, I could hear a bunch of eastern towhees, which made it feel better!

I passed a bunch of white daisies after summiting the first time. The work on the summit area has been continuing, with another widening of the Eliot Circle for trucks (I assume). I made my way onto the Skyline Trail North, admiring how shaded it is this time of year. Naturally, I was gassy on this hike, and at one point I made three stomps, farting on each stomp, and the pitches of each fart were different and accurately mimiced the final three notes of the University of Massachusetts Minuteman Marching Band's rendition of Frank Sinatra's My Way - it was remarkable.

I worked my way up and over Wolcott, Hemenway, and then Hancock. My body was just feeling tired and heavy, maybe because I had wine before bed last night? I passed some beautiful blue jays coming down Hancock Hill and I was simply not emotionally ready for the climb up Houghton. Thankfully, the climb did not humble me as badly as I thought it would. I did gas me out, but I was not passing away.

The leaves made the Skyline Trail super dark at the first stream crossing, and to my absolute delight I found some lady slippers between 1123 and the Five Corners Path!! This is where I usually find them this time of year, so I was just elated.

The second stream crossing was fully dried up and I noticed a path straight ahead before the crossing to what looks like a cave? I had never noticed it before... interesting! I made a note of it, being too lazy to investigate. I zig-zagged up to the final headwall, suffered on up, and then continued up along the shoulder for the final push, which always feels longer than I am ready for!

I listened to the northern house wrens at the summit (thank you, Merlin!) and decided to follow the other half of the red loop for my trip down, which was lovely. The swamp along the trail was mostly dry, and it looked like DCR is working on formally closing a few of the abandoned trails in that area. My final stretch of trail was cheered on by a friendly Robin, which was just lovely.

Step-by-Step

- Park at Trailside Museum.

- Start hike on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle.

- At summit road, turn left.

- At jct., turn right.

- At summit, hike around observatory clockwise, following gravel path.

- At terminus of gravel path, turn left onto Skyline Trail (blue).

- At 1063, turn right onto Skyline Trail North.

- At Hillside St., turn right onto Hillside Street.

- At jct.,. turn right onto Skyline Trail South.

- At 1066, turn left onto Eliot Circle/Skyline Trail.

- At gravel path, turn right onto Gravel Path.

- At summit, continue straight and hike spur towards ski trail.

- At jct., turn right onto Eliot Cirlce.

- After 1055, turn left onto Raccoon Hollow Path (red).

- At 1082, turn left onto Cliff Trail (red).

- Cross Summit Road, continue onto Trailside Path (red).

- Follow red dots back to car.

Blue Hills Reservation Map

Photo Album