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Massachusetts

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1,478 mi 2,378 km of trail 26 Featured Hikes

Easy Trails 517 Trails Intermediate Trails 350 Trails Hard Trails 43 Trails
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Featured Hikes in Massachusetts - 26

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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 • Loop • 2,252 ft Ascent 686.53 m Ascent

(10) Adams, MA
Favorite View from the Great Blue Hill
Intermediate/Difficult

Blue Hills Loop

4.1 mi 6.5 km • Loop • 1,171 ft Ascent 356.87 m Ascent

(16) Dedham, MA
Favorite This is from the top of the dam.
Intermediate

Tully Lake Loop

4.7 mi 7.6 km • Loop • 335 ft Ascent 102.2 m Ascent

(7) Royalston, MA
Favorite Thoreau's Cabin.
Easy

Walden Pond

1.8 mi 2.9 km • Loop • 44 ft Ascent 13.43 m Ascent

(7) Concord, MA
Favorite Experiencing the Old King's Highway seems to bring you back in time.
Intermediate/Difficult

Pamet Loop

5.4 mi 8.7 km • Loop • 239 ft Ascent 72.87 m Ascent

(2) Truro, MA
Favorite View from one of the many knobs along the RFT.
Intermediate/Difficult

Robert Frost Trail

40.2 mi 64.7 km • Point to Point • 5,360 ft Ascent 1633.58 m Ascent

(1) Wendell, MA
Favorite Start of the Pine Trail
Easy/Intermediate

Pine Tree Trail

3.7 mi 6.0 km • Loop • 216 ft Ascent 65.94 m Ascent

(1) Pocasset, MA
Favorite Muddy, rocky, and technical, this section will test your foot placement!
Intermediate

Outer Loop

2.9 mi 4.6 km • Loop • 104 ft Ascent 31.64 m Ascent

(1) Swansea, MA

Trails in Massachusetts - 884

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7.5 mi 12.1 km #1Skyline Trail
Intermediate
Winchester, MA
Intermediate
7.5 mi 12.1 km Winchester, MA 27 
89.7 mi 144.3 km #2AT: AMC - Berkshire Chapter (MA)
Intermediate
Sheffield, MA
Intermediate
89.7 mi 144.3 km Sheffield, MA
1.1 mi 1.7 km #3Skyline Trail South
Difficult
Milton, MA
Difficult
1.1 mi 1.7 km Milton, MA
0.5 mi 0.9 km #4Tannery Falls Trail
Intermediate
Adams, MA
Intermediate
0.5 mi 0.9 km Adams, MA
2.2 mi 3.6 km #5Peabody Loop
Intermediate
Dover, MA
Intermediate
2.2 mi 3.6 km Dover, MA
0.8 mi 1.2 km #6Ice Glen Trail
Intermediate
Stockbridge, MA
Intermediate
0.8 mi 1.2 km Stockbridge, MA
0.3 mi 0.5 km #7Fern Trail
Easy
Northampton, MA
Easy
0.3 mi 0.5 km Northampton, MA
1.8 mi 3.0 km #8Thunderbolt Trail
Difficult
Adams, MA
Difficult
1.8 mi 3.0 km Adams, MA
0.5 mi 0.8 km #9Needham Reservoir Trail
Easy
Needham, MA
Easy
0.5 mi 0.8 km Needham, MA
8.2 mi 13.3 km #10Bear Swamp Hiking Trail
Difficult
Charlemont, MA
Difficult
8.2 mi 13.3 km Charlemont, MA
2.7 mi 4.4 km #11Shaker Mountain Loop Trail
Intermediate/Difficult
Pittsfield, MA
Intermediate/Difficult
2.7 mi 4.4 km Pittsfield, MA
2.7 mi 4.3 km #12Hoosac Range Trail
Intermediate
North Adams, MA
Intermediate
2.7 mi 4.3 km North Adams, MA
1.1 mi 1.8 km #13Morses Pond Trail
Easy/Intermediate
Wellesley, MA
Easy/Intermediate
1.1 mi 1.8 km Wellesley, MA
2.7 mi 4.3 km #14Dome Trail
Intermediate/Difficult
Williamstown, MA
Intermediate/Difficult
2.7 mi 4.3 km Williamstown, MA
1.1 mi 1.7 km #15Cascade Trail
Intermediate
North Adams, MA
Intermediate
1.1 mi 1.7 km North Adams, MA
3.9 mi 6.4 km #16Pocumtuck Ridge Trail
Intermediate
South Deerfield, MA
Intermediate
3.9 mi 6.4 km South Deerfield, MA
0.4 mi 0.7 km #17Awesome-Sauce Trail
Extremely Difficult
Saugus, MA
Extremely Difficult
0.4 mi 0.7 km Saugus, MA
0.3 mi 0.5 km #18Ragged Mountain South Peak Trail
Intermediate/Difficult
Adams, MA
Intermediate/Difficult
0.3 mi 0.5 km Adams, MA
12.4 mi 20.0 km #19Ashuwillticook Rail Trail
Easy
Dalton, MA
Easy
12.4 mi 20.0 km Dalton, MA
1.4 mi 2.2 km #20Fire Tower Trail
Difficult
Shelburne Falls, MA
Difficult
1.4 mi 2.2 km Shelburne Falls, MA

Photos of Massachusetts - 328

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Fall fog - no druids required
May 22, 2018 near Hopkinton, 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
Red-tailed hawk at Wachusett Meadow Wildlife Sanctuary.
Nov 18, 2016 near Princeton, MA
Views from Lenox Mountain summit.
Nov 18, 2016 near Lenox, MA
The view from the ridgeline.
Jul 28, 2015 near Hadley, MA

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