The Skyline Trail traverses the Blue Hills east to west crossing many of its summits. The portion of the trail that is near Great Blue Hill makes a loop that is a great 3-mile hike. The loop ascends 5 of the 22 hills that make up the reservation (Hancock, Hemenway, Wolcott, Great Blue, and Houghton) and offers tremendous views of the Boston area. Also noteworthy are the portions of trail that are in beautiful hardwood forest that is fabulously colorful in the fall. Wildlife is abundant including songbirds, raptors, wild turkeys, squirrels, chipmunks, and deer. The Great Blue Hill Summit Tower and Blue Hill Meteorological Observatory (home to the oldest continuous weather record in North America) are highlights along this route.
Great Blue Hill at 635' is the highest peak on the Atlantic Coast south of Maine.
From I-93 take exit 3 and head north about one block. Turn right on Hillside Street and go past Houghtons Pond. Soon you'll be at the Blue Hills Reservation Headquarters which is roughly in the center of the preserve near the State Police office. Park on the east side of the road in one of two small parking lots and cross over to the west side and up to the Headquarters office then follow the signs up the dirt road. The trail takes off to the right and goes up some steep steps on its way up Hancock Hill. Overall the trail is relatively easy to follow as it is marked with blue blazes. But there are lots of intersecting trails so I recommend buying the $2 trail map at the reserve headquarters or print off the online map
The Skyline Loop Trail is about 3 miles in length. Total elevation gain/loss is about 1,100' - not all at once but rather up and down and up and down again as the loop ascends and descends 5 hills (Hancock, Hemenway, Wolcott, Great Blue, and Houghton). The ups/downs are quite steep and in some places approach Class 2.
Hiking poles are helpful on the steep downhills
Water and snacks
Sun protection, wind protection, insect repellent
($2 at the reserve headquarters)
Leash for your dog if you bring him/her along
Blue Hills Reserve
Online Trail Map
Blue Hill Meteorological Observatory
NWS Forecast for Boston, MA