Massachusetts
Looking for the best hiking in Massachusetts? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Massachusetts. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Massachusetts
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Sheffield, Massachusetts
Race Brook Falls
4.02.47 mi / 1145 ft gainHiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...Read more -
Harwich, Massachusetts
West Reservoir
4.52.48 mi / 62 ft gainThe West Reservoir Trail in Harwich, Massachusetts is a scenic destination perfect for hiking and enthusiasts and nature lovers out for a walk. This versatile trail offers a peaceful escape with beautiful surroundings and ample opportunities for outdoor activities. Trail Highlights: • Length...Read more -
Stockbridge, Massachusetts
Laura's Tower and Ice Glen
5.02.4 mi / 676 ft gainYou will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods. You will reach a split in the trail, a left will take you...Read more -
Norwell, Massachusetts
Hike the Norris Reservation Loop
2.4 mi / 60 ft gainChoose from multiple trails in Norris that offer beautiful views of the the North river and marshland. Great spot to do some trail running through the woods and see the river too. There is also a pond a short distance from the parking lot that offers a great fishing spot with a picnic table nearb...Read more -
Hampden, Massachusetts
Goat Rock Trail
2.67 mi / 659 ft gainGoat Rock Trail is an out-and-back trail where you may see beautiful wildflowers located near Hampden, Massachusetts.Read more -
Great Barrington, Massachusetts
Mt. Wilcox and Beartown Mountain Trail Loop
5.09.29 mi / 981 ft gainMt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.Read more -
Deerfield, Massachusetts
South Sugarloaf Trail
1.48 mi / 404 ft gainSouth Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.Read more -
Erving, Massachusetts
Rattlesnake Loop to Red Trail
1.97 mi / 676 ft gainRattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.Read more -
Mount Washington, Massachusetts
Mount Frissell and Brace Mountain Loop Trail
5.08 mi / 807 ft gainMount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.Read more -
Milton, Massachusetts
Houghton's Pond Recreation Area
1.2 mi / 79 ft gainHoughton's Pond Recreation Area is a loop trail that takes you by the lake located near Milton, Massachusetts.Read more -
Mount Washington, Massachusetts
Guilder Pond and Mount Washington Lookout Trail
3.92 mi / 909 ft gainGuilder Pond and Mount Washington Lookout Trail is a loop trail that takes you by the lake located near Copake Falls, New York.Read more -
Edgartown, Massachusetts
Hike Huckleberry Barrens Trail
0.5 miThe Huckleberry Barrens property is a 17 acre expanse of land in Katama, MA managed by the Sheriff's Meadow Foundation. Though the property is quite vast, the trail loop is only approximately 0.5 miles. Quite conveniently, If you're looking to extend your walk, run or bike, there is an opening ha...Read more -
Cambridge, Massachusetts
Fresh Pond Reservation Loop Trail
4.02.5 mi / 59 ft gainFresh Pond Reservation Loop Trail is a loop trail that takes you by the lake located near Cambridge, Massachusetts.Read more -
Boston, Massachusetts
Public Garden Monument Walking Tour
5.01.18 mi / 43 ft gainPublic Garden Monument Walking Tour is a loop trail that takes you by the lake located near Boston, Massachusetts.Read more -
Andover, Massachusetts
Deer Jump Reservation Loop
5.02.09 mi / 171 ft gainDeer Jump Reservation Loop is a loop trail that takes you by a river located near Andover, Massachusetts.Read more -
North Adams, Massachusetts
The Cascades Trail
4.31.97 mi / 315 ft gainThe Cascades Trail is an out-and-back trail that takes you by a waterfall located near North Adams, Massachusetts.Read more