We can't find the internet
Attempting to reconnect
Something went wrong!
Hang in there while we get back on track
Middlesex Fells Skyline Trail
Rugged reservation traverse with frequent rocky viewpoints.
Make a Day Trip
Estimated total time: Varies
Middlesex Fells Rock Circuit Trail
Rugged loop through rocky fells terrain and frequent overlooks.
Stony Brook Reservation Skyline Trail
Longer urban-forest traverse with rolling terrain and outlooks.
Breakheart Reservation Trail
Rolling woodland reservation route with pond views.
About This Trail
An 8-mile loop traversing 2,200 acres of rugged hills just 10 miles north of Boston, passing Wright’s Tower, Panther Cave, and rocky outcrops with skyline views. Pine Hill’s lookout reveals the Boston skyline with Medford, Somerville, and Charlestown spread below.
Getting There
Nearby Trails
Middlesex Fells Rock Circuit Trail
Rugged loop through rocky fells terrain and frequent overlooks.
Stony Brook Reservation Skyline Trail
Longer urban-forest traverse with rolling terrain and outlooks.
Breakheart Reservation Trail
Rolling woodland reservation route with pond views.
Lynn Woods Stone Tower Trail
Urban forest trail to historic stone tower overlooks.
Lynn Woods Dungeon Rock Trail
Forest loop to a historic cave feature in Lynn Woods reservation.
Been to Middlesex?
Share your experience and help fellow hikers discover this trail.
Write a Trail Report Report Conditions Upload Photo