Boston: Skyline Trail to Cross Fells Loop

This 12.1-mile loop skirts five reservoirs, cuts through forests of oak, hemlock, and birch, and gains 2,600 feet of elevation in 2,060-acre Middlesex Fells Reservation.
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This 12.1-mile loop skirts five reservoirs, cuts through forests of oak, hemlock, and birch, and gains 2,600 feet of elevation in 2,060-acre Middlesex Fells Reservation.

Trail Facts

  • Distance: 18.8

Waypoints

CFL001

Location: 42.438233, -71.119523

Start near park map; L in a few yards on white-blazed Skyline Trail

CFL002

Location: 42.463959, -71.11972

Hard L behind firehouse; continue on Skyline Trail

CFL003

Location: 42.463745, -71.108322

Hard L; follow blue blazes to Bear Hill Tower, views of Boston, ocean, and North Reservoir; retrace blue trail back to Skyline and turn L

CFL004

Location: 42.461929, -71.107712

Bear R (hard-to-spot blaze on tree)

CFL005

Location: 42.459949, -71.107658

Picnic on rock ledge overlooking North Reservoir

CFL006

Location: 42.45269, -71.106102

Follow blazes through parking lot to continue on Skyline

CFL007

Location: 42.447617, -71.107376

Hard L onto Brooks Rd.; follow blue-blazed Cross Fells Trail

CFL008

Location: 42.448101, -71.10556

Hard R under bridge (I-93); quick L to continue on Cross Fells Trail

CFL009

Location: 42.444992, -71.091835

L onto Rock Circuit Trail (white blazed)

CFL010

Location: 42.439877, -71.078026

Bear R (or go straight for short, steep scramble to Pinnacle Rock for cliff-top views)

CFL011

Location: 42.444775, -71.091873

L to rejoin blue-blazed Cross Fells

CFL012

Location: 42.447643, -71.106888

Turn L onto white-blazed Skyline Trail

CFL013

Location: 42.433109, -71.104874

Wright?s Tower, views of Boston skyline; R down road 150 ft; L into woods on Skyline Trail; follow white blazes 1.2 miles back to trailhead