Trails by State · All 50

Hike your home state

The standout trail in every US state — with mileage, elevation gain, difficulty, season notes, and a live trail map. Pick a state and start planning the next weekend out.

Top trails in Massachusetts (5)

Mt Greylock SR
Hard
Mt Greylock via Hopper Trail

Massachusetts's high point on the Appalachian Trail. 3 mi with about 2,650 ft of elevation gain. This is a challenging hike with real elevation and exposure in places; start early, pack layers, and check current trail conditions before you go.

Distance:
10.3 mi
Gain:
2,650 ft
Type:
Loop
Great Barrington
Moderate
Monument Mountain Loop

Quartzite cliffs Hawthorne and Melville climbed together in 1850. 0 mi with about 720 ft of elevation gain. Expect a steady workout with some sustained climbing — solid footwear and a couple of liters of water are recommended.

Distance:
3.0 mi
Gain:
720 ft
Type:
Loop
Blue Hills Reservation
Hard
Skyline Trail

Boston's backyard ridge walk. 0 mi with about 1,300 ft of elevation gain. This is a challenging hike with real elevation and exposure in places; start early, pack layers, and check current trail conditions before you go.

Distance:
9.0 mi
Gain:
1,300 ft
Type:
Loop
Sutton
Moderate
Purgatory Chasm Loop

Short scramble through a granite chasm. 0 mi with about 150 ft of elevation gain. Expect a steady workout with some sustained climbing — solid footwear and a couple of liters of water are recommended.

Distance:
1.0 mi
Gain:
150 ft
Type:
Loop
Walden Pond SR
Easy
Pond Path

Thoreau's pond, with a replica cabin at the trailhead. 9 mi with about 30 ft of elevation gain. It is a beginner-friendly route that families and casual day hikers can comfortably complete, even in shoulder seasons.

Distance:
1.9 mi
Gain:
30 ft
Type:
Loop