Massachusetts

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2,112 mi 3,400 km of trail — 59 Recommended Routes

1 Gem

495 Trails Intermediate Trails

580 Trails Hard Trails

193 Trails

Areas Within Massachusetts

Cape Cod and the Islands

23 Trails

Central Massachusetts

Western Massachusetts

219 Trails

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Gems in Massachusetts - 1

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Bash Bish Falls

(1) Sheffield, MA

Recommended Routes in Massachusetts - 59

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Skyline Trail

7.5 mi 12.1 km • 846' Up 257.71 m Up • 863' Down 262.89 m Down

Winchester, MA

Beautiful section of the AT just as the snow/ice was beginning to melt on the ridge

Mount Greylock Summit Loop

6.6 mi 10.6 km • 2,252' Up 686.53 m Up • 2,250' Down 685.67 m Down

Adams, MA

A beautiful look at the fall leaves that are just beginning to turn color.

Ponkapoag Pond Loop

4.4 mi 7.0 km • 229' Up 69.67 m Up • 228' Down 69.44 m Down

Milton, MA

Running through 30 minutes before sunset.

Leyden Blueberry Fields

7.5 mi 12.1 km • 1,167' Up 355.66 m Up • 1,188' Down 362.11 m Down

Bernard…, MA

Blue Hills Loop

4.1 mi 6.5 km • 1,171' Up 356.87 m Up • 1,165' Down 355.22 m Down

Dedham, MA

Tully Lake Loop

4.7 mi 7.6 km • 335' Up 102.2 m Up • 331' Down 100.98 m Down

Royalston, MA

Walden Pond

1.8 mi 2.9 km • 44' Up 13.43 m Up • 43' Down 13.18 m Down

Concord, MA

Trail is unmarked but follows the edge of large field.

Robert Frost Trail

40.2 mi 64.7 km • 5,360' Up 1633.58 m Up • 5,892' Down 1795.84 m Down

Wendell, MA

Trails in Massachusetts - 1209

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89.7 mi 144.4 km #1AT: AMC - Berkshire Chapter (MA) Intermediate/Difficult Sheffield, MA	Intermediate/Difficult	Sheffield, MA	2
0.8 mi 1.2 km #2Ice Glen Trail Intermediate Stockbridge, MA	Intermediate	Stockbridge, MA	2
3.9 mi 6.4 km #3Pocumtuck Ridge Trail Intermediate South Deerfield, MA	Intermediate	South Deerfield, MA	1
1.8 mi 3.0 km #4Thunderbolt Trail Difficult Adams, MA	Difficult	Adams, MA	1
0.3 mi 0.5 km #5Fern Trail Easy Northampton, MA	Easy	Northampton, MA	2
0.5 mi 0.8 km #6Needham Reservoir Trail Easy Needham, MA	Easy	Needham, MA	1
8.2 mi 13.3 km #7Bear Swamp Hiking Trail Difficult Charlemont, MA	Difficult	Charlemont, MA	1
0.9 mi 1.4 km #8Hermit's Castle Trail Intermediate Erving, MA	Intermediate	Erving, MA	1
1.4 mi 2.2 km #9Fire Tower Trail Difficult Shelburne Falls, MA	Difficult	Shelburne Falls, MA	1
1.1 mi 1.8 km #10Morses Pond Trail Intermediate Wellesley, MA	Intermediate	Wellesley, MA	1
10.9 mi 17.6 km #11Mahican - Mohawk Trail Section 4: Charlemont - Cold River Difficult Charlemont, MA	Difficult	Charlemont, MA	1
2.7 mi 4.3 km #12Hoosac Range Trail Intermediate North Adams, MA	Intermediate	North Adams, MA	1
0.4 mi 0.7 km #13Pine Hill Trail Intermediate Princeton, MA	Intermediate	Princeton, MA	1
2.7 mi 4.3 km #14Dome Trail Difficult Williamstown, MA	Difficult	Williamstown, MA	1
1.5 mi 2.5 km #15Healthy Heart Trail Easy Melrose, MA	Easy	Melrose, MA	1
1.1 mi 1.7 km #16Cascade Trail Intermediate North Adams, MA	Intermediate	North Adams, MA	1
2.1 mi 3.4 km #17Wickett Pond Trail Intermediate Wendell, MA	Intermediate	Wendell, MA	1
0.4 mi 0.7 km #18Awesome-Sauce Trail Very Difficult Saugus, MA	Very Difficult	Saugus, MA	1
0.3 mi 0.5 km #19Ragged Mountain South Peak Trail Difficult Adams, MA	Difficult	Adams, MA	1
12.4 mi 20.0 km #20Ashuwillticook Rail Trail Easy Dalton, MA	Easy	Dalton, MA	1