Pittsfield, Massachusetts
Looking for the best hiking in Pittsfield? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Pittsfield. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Pittsfield
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Elka Park, New York
Devil's Path to Devil's Tombstone
5.011.9 mi / 4475 ft gainThe Eastern half of Devil's Path has four major summits: Indian Head, Twin, Sugarloaf and Plateau. Each summit is a straight climb up and down, then back up to as much as 3,900 ft. There are some sparse sections of level ground, but most is a steep descent uphill or steep slide downhill. Your ...Read more -
Elka Park, New York
Devil's Path in the Catskills
4.022.04 mi / 7733 ft gainDevil's Path is roughly more than 24 miles long, althought it feels like an eternity of milage. Going thru the summits of Indian head, Twin, Sugarloaf, Plateau, Hunter, and Westkill Mountains. Its brutal. Its painful, Its unique. Be prepared for anything and everything. You will encounter wild l...Read more -
Simsbury, Connecticut
Hike to the Heublein Tower on Talcott Mountain
4.32.54 mi / 404 ft gainThe Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...Read more -
Windham, New York
Escarpment Trail
21.97 mi / 5282 ft gainThe Escarpment Trail runs the length of the Catskill Escarpment. The Escarpment rises steeply from the valley below forming the northeast corner of the Catskill Mountains. It offers great views toward the Adirondack Mountains to the north and the great Hudson River to the east. The trail is moder...Read more -
Kent, Connecticut
Hike the Ridge Loop Trail, Macedonia Brook SP
3.0For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...Read more