Great Blue Hill Skyline Loop Hiking Guide
Great Blue Hill is the high point of the Blue Hills Reservation, a 7,000-acre DCR park that starts only minutes from downtown Boston. The Skyline Loop is the classic way up: it leaves Reservation Headquarters in Milton on the north branch of the Skyline Trail, rolls over a string of ledgy summits to the stone Eliot Tower, and comes back on the south branch. It is short enough for an afternoon and steep enough that you will feel it.
The Loop, Hill by Hill
DCR's trail map describes the Skyline Loop as the link between the north and south branches of the Skyline Trail, running between Reservation Headquarters and Eliot Observation Tower and summiting five hilltops over steep, rocky terrain. Follow the blue blazes from headquarters heading west. AllTrails lists the circuit at 3.3 miles with about 820 feet of gain. The route goes up stone steps onto Hancock Hill, crosses Hemenway and Wolcott Hills, and tops out on Great Blue Hill at 635 feet, the tallest of the 22 hills in the chain. To come back, cross the granite Eliot Memorial Bridge to intersection 1066 and bear left onto the south branch.
Eliot Tower and the Observatory
The fieldstone Eliot Tower was built in 1929 and honors Charles Eliot, the landscape architect behind the reservation. On a clear day the Friends of the Blue Hills say you can pick out Mount Monadnock in New Hampshire, roughly 70 miles off, along with downtown Boston and Massachusetts Bay. At the other end of the flat summit stands the Blue Hill Observatory, keeping weather records since 1885. Its self-guided tour costs $10 per person (members free) and is open Tuesday to Friday from 10 a.m. to 2 p.m.; weekend hours run 10 a.m. to 5 p.m. through the summer season and 10 a.m. to 4 p.m. from mid-October. It is closed Mondays and all of January.
Parking and Getting There Without a Car
The spaces right at Reservation Headquarters are 10-minute parking for picking up maps. Hikers use the designated spaces across Hillside Street from the headquarters building; the Friends of the Blue Hills give the address as 695 Hillside Street, Milton. Houghton's Pond, a short way down Hillside Street, has a free visitor lot if those fill. DCR's map notes that parking across the reservation is limited and weekend use is heavy. Without a car, DCR points to the MBTA 716 bus from Mattapan, which serves the Trailside Museum on the hill's west side, but its schedule is unusual, so check it before relying on it. There is no parking fee at either lot.
Dogs, Snakes and Hunt Season
Dogs are welcome on the trails but must stay leashed; DCR's statewide rule caps leashes at 10 feet and requires proof of rabies vaccination. Pets are not allowed on the Trailside Museum grounds or on the Houghton's Pond beach. The hills are home to small, protected populations of timber rattlesnakes and northern copperheads. DCR says they avoid people and bite only when provoked, which is one more reason to stay on the marked path and keep your dog close. DCR runs a deer management program in the reservation each fall; check the reservation page for dates before a late-season hike.
Footing and Timing
Most of the loop is bare granite and loose stone, and the descents are steeper than they look from the top. Rock that is fine when dry turns greasy after rain and icy in winter, when traction devices earn their place. The reservation is open dawn to dusk. DCR warns that weekend use is heavy; a weekday or an early start gets you the tower without a crowd.
Hiking tips for Great Blue Hill Skyline Loop
- Park across Hillside Street from headquarters; the lot by the building is 10-minute only.
- Look for the four-digit intersection numbers on white posts and match them to the DCR map.
- Bring microspikes in winter; the ledges on the south branch ice over first.
- Climb the tower stairs for the full view; the summit trees block much of it at ground level.
- Keep dogs on a leash of 10 feet or less and away from any snake you spot.
Nearby trails to explore
- Skyline Trail Traverse (Blue Hills)
- Noanet Peak Loop
- World's End Carriage Path Loop
Hike this trail with TrailMates
Five summits and a stone tower, all inside Route 128. Use TrailMates to find Boston hikers heading to Great Blue Hill. Download the TrailMates app to connect.