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Massachusetts

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2,118 mi 3,409 km of trail 60 Recommended Routes

Gems 1 Gem Easy Trails 493 Trails Intermediate Trails 587 Trails Hard Trails 190 Trails
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Gems in Massachusetts - 1

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gem Favorite Big Bish Falls from above.

Bash Bish Falls

(1) Sheffield, MA

Recommended Routes in Massachusetts - 60

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Favorite Middlesex Fells, Medford, United States
Intermediate/Difficult

Skyline Trail

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

Winchester, MA
Favorite Beautiful section of the AT just as the snow/ice was beginning to melt on the ridge
Intermediate/Difficult

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

Ponkapoag Pond Loop

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

Milton, MA
Favorite Long exposure of Doane's Falls.
Intermediate

Tully Lake Loop

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

Royalston, MA
Favorite The Great Blue Hill Observation Tower
Difficult

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
Favorite Running through 30 minutes before sunset.
Intermediate

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
Favorite Thoreau's Cabin.
Easy

Walden Pond

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

Concord, MA
Favorite Lake by the parking area
Intermediate/Difficult

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 - 1210

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89.7 mi 144.4 km #1AT: AMC - Berkshire Chapter (MA)
Intermediate/Difficult
Sheffield, MA
Intermediate/Difficult
Sheffield, MA
1.8 mi 3.0 km #2Thunderbolt Trail
Difficult
Adams, MA
Difficult
Adams, MA
0.8 mi 1.2 km #3Ice Glen Trail
Intermediate
Stockbridge, MA
Intermediate
Stockbridge, MA
3.9 mi 6.4 km #4Pocumtuck Ridge Trail
Intermediate
South Deerfield, MA
Intermediate
South Deerfield, MA
0.5 mi 0.8 km #5Needham Reservoir Trail
Easy
Needham, MA
Easy
Needham, MA
0.3 mi 0.5 km #6Fern Trail
Easy
Northampton, MA
Easy
Northampton, MA
8.2 mi 13.3 km #7Bear Swamp Hiking Trail
Difficult
Charlemont, MA
Difficult
Charlemont, MA
0.4 mi 0.7 km #8Pine Hill Trail
Intermediate
Princeton, MA
Intermediate
Princeton, MA
0.9 mi 1.4 km #9Hermit's Castle Trail
Intermediate
Erving, MA
Intermediate
Erving, MA
2.7 mi 4.3 km #10Hoosac Range Trail
Intermediate
North Adams, MA
Intermediate
North Adams, MA
1.4 mi 2.2 km #11Fire Tower Trail
Difficult
Shelburne Falls, MA
Difficult
Shelburne Falls, MA
1.1 mi 1.8 km #12Morses Pond Trail
Intermediate
Wellesley, MA
Intermediate
Wellesley, MA
10.9 mi 17.6 km #13Mahican - Mohawk Trail Section 4: Charlemont - Cold River
Difficult
Charlemont, MA
Difficult
Charlemont, MA
2.7 mi 4.3 km #14Dome Trail
Difficult
Williamstown, MA
Difficult
Williamstown, MA
1.5 mi 2.5 km #15Healthy Heart Trail
Easy
Melrose, MA
Easy
Melrose, MA
1.1 mi 1.7 km #16Cascade Trail
Intermediate
North Adams, MA
Intermediate
North Adams, MA
2.1 mi 3.4 km #17Wickett Pond Trail
Intermediate
Wendell, MA
Intermediate
Wendell, MA
2.4 mi 3.8 km #18Yokun Ridge Trail
Intermediate
Lenox, MA
Intermediate
Lenox, MA
0.3 mi 0.5 km #19Ragged Mountain South Peak Trail
Difficult
Adams, MA
Difficult
Adams, MA
12.4 mi 20.0 km #20Ashuwillticook Rail Trail
Easy
Dalton, MA
Easy
Dalton, MA

Photos of Massachusetts - 619

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Misty river at sunrise.
Jan 22, 2020 near Chester…, MA
Fall fog - no druids required
May 22, 2018 near Hopkinton, MA
The trail requires crossing the river multiple times.
Mar 28, 2020 near Sheffield, MA
walk through pine trees forest at beginning of trail.
Mar 28, 2020 near Sheffield, MA
Foliage in fall
May 22, 2018 near Upton, MA
Looking west from one of the many outlooks on this beautiful ridgeline.
Nov 18, 2016 near South A…, MA
We love big trees!
Aug 26, 2016 near Chester…, MA
Experiencing the Old King's Highway seems to bring you back in time.
Jul 5, 2017 near Truro, MA