Boston Trails

Boston: Skyline Trail Loop

On this 6-mile loop in Blue Hills Reservation, you'll see dense hardwoods, meadows, ponds, glacial leftovers, rocky hills, and sweeping views of Boston.

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Trail Facts

  • Distance: 9.7



Location: 42.2145652770996, -71.0698852539062

Hop on blue-blazed Skyline Trail to Blue Hills Reservation


Location: 42.2123489379883, -71.0925140380859

Swing R @ 2054 marker onto gravel road, then cross Hillside St.


Location: 42.2143516540527, -71.0941009521484

Look for blue-blazed North Skyline Trail to L of park HQ building


Location: 42.2169990539551, -71.102668762207

Five Corners; bear R, staying on Skyline toward Great Blue Hill


Location: 42.2161483764648, -71.1055145263672

Quick side trip: Bear R @ Y for beautiful picnic spots near two ponds; return to main trail and turn R for Woolcott Hill. Then it’s a steep, rocky ascent of Great Blue Hill


Location: 42.2135848999023, -71.112663269043

Summit: Stone tower with views of skyline and harbor. Continue W on Skyline Trail .1 mi. to weather observatory (founded 1885) then retrace E on Skyline Trail for .05 mi. and turn R onto S. Skyline Trail


Location: 42.2125816345215, -71.1126480102539

R onto blue-blazed S. Skyline Trail for rocky descent, then uphill through pines and past glacial remains


Location: 42.212818145752, -71.0968170166016

Cross Hillside St.; L then quick R through parking lot, following Skyline Trail; in .1 mi., when Skyline Trail goes L, continue straight on gravel road then bear L on paved Bugbee Path, heading uphill


Location: 42.2110176086426, -71.0899047851562

L onto orange-blazed Massachuseuck Trail (where road widens); at next T-junction, go L onto Doe Hollow Path


Location: 42.2130813598633, -71.0789794921875

Bear R, leaving Doe Hollow Path; continue on orange-blazed trail; gradual climb on loose rock and packed-dirt trail


Location: 42.2146835327148, -71.0715866088867

R to rejoin Skyline Trail (blue and orange trails overlap) to trailhead