Monday, April 20, 2026

Skyline Traverse Eastbound (Blue Hills Reservation)

Skyline Traverse Eastbound (Blue Hills Reservation)

Hike Type: Traverse
Distance: 8.51 miles
Elevation: 1,841 feet
Time: 4 hours, 14 minutes (3 hours, 53 minutes moving)
Parking: Drop Car #1 at Shea Memorial Rink in Quincy. Drive Car #2 and park at cul-de-sac at the end of Royall Street in Canton on side of road.
Hiking Challenges: Trail Trace the Blue Hills; Great Blue Hill Summits


The Hike 
Reunited with Sarah for a Skyline Traverse! I hadn't gotten a new patch in a while, nor have I done a traverse of the Skyline Trail in years, so it was time! We agreed to meet in Quincy at 7:30am and get started with our hike at 8:00am. It was nice and exciting to be getting a bigger hike in so close to home. I had plans around 1:00pm, so I was hoping to be back in time for that, we'll see!

[7:56am - Start of Hike]
We started on the access path toward the actual start of the Skyline Trail at 7:56am. It was a nice morning with blue skies, warm sun, a cooler temperatures in the high 40s/low 50s. At the terminus of the access path, we turned left onto the Skyline Trail, pretending that we weren't actually on the trail yet. I never understand why they have the trail start in such an awkward-to-get-to place. We hopped along the murky streams and litter-covered rocks, eventually OFFICIALLY starting our traverse!

[8:01am - Skyline Trail]
We hit the abandoned highway interchange, officially beginning our traverse! We retraced our steps and continued onward, missing the spur to Royall Street that I needed (oh well), crossing Green Street, climbing up and down Little Blue Hill, crossing paths with an... interesting fellow, and carefully crossing MA-138.

[8:26am - Skyline Trail/MA-138]
Thankfully the crossing wasn't too horrible. The steep climb up Great Blue Hill had both of us huffing and puffing, but thankfully the sunny views helped push us along higher up! We could clearly make out Mt. Wachusett from the view, which was a fun little treat, and we loved seeing the early springtime buds on the trees. 

We did take a side-path to the true summit to "boop" the plaque, and then we continued to the Eliot Tower, which gave us a wonderful view of Boston.

Our hike continued down Great Blue Hill, up and over Wolcott Hill, and then up and to the viewpoint on Hemenway Hill, which was just beautiful. It was nice to be on super-familiar trail, but more fun to be continuing on afterwards! We descended Hemenway and went up and over Hancock before making our way to Hillside Street.

[9:34am - Skyline Trail/Hillside Street]
The Hillside Street crossing was nice and easy and the walk up the Bugbee merge was lovely. We dipped off back fully into the woods and started our surprisingly heart-pounding climb up Tucker Hill (I always forget how rugged this side is, too). We scrambled down Tucker Hill, talking about what big hike we want to do next (maybe Lafayette tomorrow??), and then went up and over North Boyce before a final push up Buck Hill for a sit and snack. It was SO NICE out, but still a little chilly with a breeze. 

[10:32am - Skyline Trail/MA-28]
We got lucky with the timing of our MA-28 crossing and continued on into the woods, spotting an old orange blaze (which I love finding). We both took potty breaks in the flat stretch between the Pipe Line and Chickatawbut Hill - we were so joyful to be relatively alone in the woods - the perks of hiking on a Monday!

We steeply scrambled up Chickatawbut Hill, enjoying the view back towards Buck Hill, and then continued past Fenno, Kitchamakin, and enjoying the beautiful views of Boston and the ocean from Nahanton and the nicely laid stone steps all around.

We continued over the four and a half broken hills, admiring the beautiful forests in this area, alongside MANY Eastern Towhee birds and the old fenceposts. We were joined by a few hikers on the final broken hill, and easily descended to cross Chickatawbut Road.

[11:34am - Skyline Trail/Chickatawbut Road]
(EDIT: Writing this with time stamps, I'm really enjoying that we spent almost exactly an hour in each section of the park). Almost in the home stretch! We had a steep-but-short climb up Wampatuck Hill and enjoyed the partial views. We were both in-and-out of void time at this point of our hike, which wasn't a bad thing at all. We enjoyed the views into the little swampy pond after Wampatuck, and then had a STEEP, scrambly climb up to The Crags, which has one of my favorite unique views in the park.

We descended the Crags and went up and over the shoulder of Rattlesnake Hill, past Sullivan's Quarry, crossed Wampatuck Road, and had our final push across the St. Moritz Ponds and to Sarah's car! Yay! I was NOT making it to my 1:00pm plans, but we weren't TOO far off!

[12:10pm - End of Hike]
We got my car, got nice and changed, and locked in our plans to hike Mt. Lafayette tomorrow! We'd have a 4:00am departure time, meeting at the Burlington Mall to drop a car at 4:30 for the drive up. The weather was looking not-freezing, virtually wind-less, and CLOUD-FREE! Should be a great day!

Once home, I got showered, packed, and headed to Chrsitien's to see RAYE at the MGM Music Hall that night!

Step-by-Step
- Park at end of Royall Street and enter woods.
- At terminus of path, turn left onto Skyline Trail.
- At terminus/pavement, turn around.
- Follow Skyline Trail to eastern terminus at Shea Memorial Rink in Quincy.

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