Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Hike Type: Mostly Lollipop Loop

Distance: 4.54 miles

Elevation: 640 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hour, 35 minutes

Parking: Room for 20-30 cars at Chickatawbut Overlook.
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Blue Hills Grid

The Hike 

I made my way back to the Blue Hills after school, suffering through another afternoon of "unusually heavy traffic." The inspiration for this hike was the Blue Hills Grid that I've been "working" on for years now, plus my second Trail Trace map. I had field day today, so I had been outside for a lot of the afternoon, but I was excited to keep the momentum going! It was 78 degrees out and overall pretty pleasant!

I made my way into the woods and up to the tower before following the yellow blazes counter-clockwise. I stopped for a quick potty break and managed to pee on my hip belt strap... Ugh. I worked my way up Thayer Path, which was grassy up around the summit fence (I had tick anxiety). I went down Carve Path, which had it's trademark giant rock piles that I've always been wildly curious about. 

I then made my way down onto the Bouncing Brook Path, which I'd be following for a while. It was darker and more humid down there, and I was following horse prints for most of the walk. I passed some lovely purple flowers, which were lesser periwinkle, not violets. I passed a really nice stone wall I hadn't noticed before just before the junction with Lee Path, and then a lady slipper just before the junction with Sassaman! Just kidding! At the junction with Curve Path! I missed a turn! That's fine, my hike was going to be a bit longer.

Everytime I'm hiking these interior Chickatawbut trails I'm reminded of how long they feel - it must be because there's a thinner density of trails in this area, or something. The bugs were present but not much of a bother as long as I kept on moving. I worked up Wampatuck Path and then the Pocapawmet Path to join the Skyline Trail!

I don't think I have traveled this direction on the Skyline Trail since a hike with Gen and Wylie in the winter of 2021 or 2022 - it's been a minute! I passed a super cute eastern towhee on my way up Broken Hill #4 and then maneuvered the rockiness that surrounds #3 - there were baby blueberries! A deer magically lept across the trail as I was climbing up #2 and there were some young rock harlequin flowers at the top. 

The climb up #1.5 was also rockier than I had realized traveling in the other direction, and I found myself wondering how different the forest would be on #1 in 10, 20, 50 years since the last fire. It looked like most of the pines were dead/dying and the undergrowth was growing in strong! I passed more pink lady slippers and rock harlqeuins as I descended #1, and then I started my climb up Nahanton.

The climb up the Chickatawbut Ridge was actually more gradual than I was emotionally ready for. I climbed on up Nahanton, past some more baby blubes, and found myself wondering yet again about the old foundation-like things. I admired the stone steps up Kitchamakin and suffered through the brush to reach the true top of Fenno Hill before making my way up to Chickatawut Hill. I descended via Stowe Path and made it back to the car - this was officially a zero-person hike! I dusted the pollen off of myself (literally) and heard a barrel owl calling somewhere on the other side of the road.

Step-by-Step

- Park at Chickatawbut Overlook.

- Start hike on Tower Path (yellow).

- At 3075, turn left onto Sassaman Notch Path (yellow).

- At second jct., turn right onto Thayer Path.

- At fence, turn left.

- At second jct., continue right onto Skyline Trail (blue).

- At 3065, turn left onto Carve Path.

- At 3051, turn left onto Bouncing Brook Path (red). 

- At 3152, turn left onto Wampatuck Path.

- At 3171, turn around and turn right onto Pocapawmet Path (unmapped).

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

- At Chickatawbut Hill, turn right onto Thayer Path, then turn right again onto Stowe Path.

- At jct., turn left to stay on Stowe Path.

- At terminus, turn left onto Sassaman Notch Path (yellow).

- At 3075, turn right onto Tower Path (yellow).

- Follow Tower Path back to car.

Blue Hills Reservation Map

Photo Album