With so many trails in the area, it's easy to shorten or lengthen this loop hike for any ability or time. As a complete tour, though, this hits many of the best hills around Houghton Pond for a great workout or day hike adventure. In total, this loop hits five of the main hills starting with Breeze Hill, Burnt Hill, Buck Hill, Boyce Hill, and Tucker Hill.
The view from Buck Hill is an amazing reward and a neat way to see the Boston skyline. A great reminder of how close you can still be to the city while feeling like you're in the wild.
This lollipop-style loop starts from one of the main parking areas at the Houghton Pond Visitor's Center. Here you'll find more information, a concession stand, and restroom. Follow the Green Dot - Breeze Hill
trail east toward marker 2053 and then take a left (north) to begin the first climb up Breeze Hill. Look for the first right onto Bugbee Path
marked by green dots and white triangles.
From here, continue east toward Burnt Hill leaving the green dots at marker 2096, but staying with the white triangles toward marker 2111 and then 2129. Here, turn right for an extra little loop to link up with Beech Hollow Path
(you can also continue straight to marker 2135 and bypass this little loop).
As you near Randolph Avenue on the Oblique Path
and Forest Path Connector
, you'll begin heading to the left (north) to start the climb up toward the Skyline Trail
and then the highlight of the loop: Buck Hill. This half-mile section is the longest climb but the summit of Buck Hill is worth the effort.
From there, continue back west, heading downhill toward Boyce Hill on the Forest Path
. Use the Dark Hollow to Deer Hollow Connector
to get over to Tucker Hill for the last major climb of the loop on the Skyline Trail
. From here, continue heading south back toward Breeze Hill and Houghton Pond to complete the loop.
The Civilian Conservation Corps did extensive work in Blue Hills Reservation between 1933 and 1937, adding trails, masonry, and the camp east of Randolph Avenue.