Charlemont, Massachusetts
Looking for the best hiking in Charlemont? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Charlemont. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Charlemont
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Great Barrington, Massachusetts
Hike Monument Mountain
4.52 mi / 720 ft gainAt 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...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 -
Glen Road, Vermont
Hike the Lye Brook Falls Trail
4.04.7 mi / 938 ft gainThe Lye Brook Falls Trail is a 4.7 mile hike through scenic trails just outside of Manchester Center, Vermont. The trail is open year-round, but the best time to go is during spring blooms or to see the fall colors. This hike is family friendly and fun for all ages. Dogs are allowed on this trail...Read more -
Sandisfield, Massachusetts
Buck River Swimming Hole
4.00.3 mi / 250 ft gainThis swimming hole is 7-feet deep. At the top of the swimming hole is a 12-foot waterfall with slide down. Parking: The swimming hole is located between Sandisfield Town Office and the post office. There is one dirt pull-off space near the swimming hole. The easiest parking is at the Town Offic...Read more -
Jaffrey, New Hampshire
Hike MT Monadnock via White Arrow Trail
4.3 mi / 1485 ft gainArriving at the Old Toll Road/Halfway House Trail head you will have $5 entrance fee. Starting on the Old Toll road you'll find yourself walking on a gradual incline into the beautiful New Hampshire wilderness. Everything you see and smell is fresh and vibrant. Following the road for 1.1 miles yo...Read more -
Jaffrey, New Hampshire
Summit Mt. Monadnock via Marlboro Trail
5.04 mi / 2300 ft gainStart at the Marlboro Trailhead (you can enter this in Google maps) off Shaker Road. There's parking and porta-potty bathrooms. The trail is well-marked with white dashes/M marks all the way up. Once on trail, the initial 800 ft climb is through forested terrain with a few brooks and streams alon...Read more -
Jaffrey, New Hampshire
Mount Monadnock via White Dot Trail
4.53.46 mi / 1699 ft gainMonadnock State Park is located in and around the 3,165-ft. Mount Monadnock. Mount Monadnock is crisscrossed by many miles of well-maintained hiking trails. The popular White Dot Trail (2.2 miles) is the shortest but steepest ascent to the summit, accessible from the Monadnock State Park headquar...Read more -
Jaffrey, New Hampshire
Mount Monadnock via White Dot & White Cross Loop
4.53.7 mi / 1686 ft gainThe White Dot Trail is the shortest, steepest ascent to the summit, while White Cross has a slightly easier grade down with very little difference in distance. Therefore, per the park's rangers, the best way to conquer this loop is White Dot up, White Cross down.The White Dot Trail begins at Mon...Read more -
Norfolk, Connecticut
Campbell Falls
4.00.99 mi / 161 ft gainCampbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....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 -
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 -
Granby, Connecticut
Enders Falls
4.00.5 mi / 118 ft gainEnders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut. Enders has a good sized parking lot directly on Route 219. From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...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 -
Dorset, Vermont
Hike 'The Merck'
4.02.5 miOf the 10 trails at The Merck, The Wildlife Trail is a great hike through the forest that offers you the best way to see wildlife, streams and tracks. You can do the whole hike as a loop in about 2-2 1/2 hours or shorten it up with some shortcuts if you just want a quick hike. Great for family ...Read more -
Mount Washington, Massachusetts
Bash Bish Falls
4.30.75 mi / 295 ft gainBash Bish Falls is a spectacular 60-foot waterfall located on the Massachusetts-New York border in the southern Berkshires. This popular destination offers easy hiking access and stunning natural beauty, making it perfect for families and casual hikers. Parking Options Massachusetts Side: 0...Read more -
Copake, New York
Bash Bish Falls from Taconic State Park
1.53 mi / 167 ft gainBash Bish Falls from Taconic State Park is an out-and-back trail that takes you by a waterfall located near Copake, New York. Swimming is not permitted at Bash Bish Falls.Read more