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Boston, MA: Blue Hills Skyline Trail LoopBackpacker Magazine

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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Author: Backpacker Magazine
Activity: Hiking
State: Massachusetts (MA)
Distance: 6.03 mi 
Difficulty: 4 / 10
Rating: Unrated  
Rate this trip

-Photos by Michael Blair

TO TRAILHEAD: I-93 S to exit 5B (MA 28 N/Milton). Take MA 28 N for .5 mi. and park in small dirt clearing on L.

DIRECTIONS + WAYPOINTS: helping you find your way

Position Format: Datum:
Tracks

BSL01

Distance: 6.03 mi Points: 522
Total Time: none Speed: 0.0 mph Pace: 0:00 / mi
Active Time: none Speed: 0.0 mph Pace: 0:00 / mi
Skyline Trail Loop

Points of Interest

Summit Tower

Location: 42.213485, -71.112700
© Michael Blair

BSL001

Location: 42.214565, -71.069885
Hop on blue-blazed Skyline Trail to Blue Hills Reservation

BSL002

Location: 42.212349, -71.092514
Swing R @ 2054 marker onto gravel road, then cross Hillside St.

BSL003

Location: 42.214352, -71.094101
Look for blue-blazed North Skyline Trail to L of park HQ building

BSL004

Location: 42.216999, -71.102669
Five Corners; bear R, staying on Skyline toward Great Blue Hill

BSL005

Location: 42.216148, -71.105515
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

BSL006

Location: 42.213585, -71.112663
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

BSL007

Location: 42.212582, -71.112648
R onto blue-blazed S. Skyline Trail for rocky descent, then uphill through pines and past glacial remains

BSL008

Location: 42.212818, -71.096817
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

BSL009

Location: 42.211018, -71.089905
L onto orange-blazed Massachuseuck Trail (where road widens); at next T-junction, go L onto Doe Hollow Path

BSL010

Location: 42.213081, -71.078980
Bear R, leaving Doe Hollow Path; continue on orange-blazed trail; gradual climb on loose rock and packed-dirt trail

BSL011

Location: 42.214684, -71.071587
R to rejoin Skyline Trail (blue and orange trails overlap) to trailhead



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