Sunderland, Massachusetts
Looking for the best hiking in Sunderland? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Sunderland. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Sunderland
-
Holyoke, Massachusetts
Whiting Street Reservoir Loop
3.74 mi / 138 ft gainWhiting Street Reservoir Loop is a loop trail that takes you by a lake located near Holyoke, Massachusetts.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
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 -
Jaffrey, New Hampshire
Mount Monadnock via White Dot Trail
4.43.46 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 -
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 -
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 -
Franklin, Connecticut
Hike Baileys Ravine at Ayer's Gap Preserve
1.6 mi / 314 ft gainIt's steep and rocky in the beginning but it levels out after a while! When standing in the parking lot, the trailhead is hidden! Look to the right. The trail ends on Ayer's Road so you have to walk back a little ways on the road.Read more -
Londonderry, New Hampshire
Kendall Pond Yellow and Blue Trails
1.18 mi / 223 ft gainKendall Pond Yellow and Blue Trails is a loop trail that takes you through a nice forest located near Londonderry, New Hampshire.Read more -
Hanson, Massachusetts
Burrage Pond Indian Trail
5.03.39 mi / 194 ft gainBurrage Pond Indian Trail is an out-and-back trail where you may see beautiful wildflowers located near Hanson, Massachusetts.Read more -
Bedford, New Hampshire
Pulpit Rock Conservation Area Loop
4.82.4 mi / 0 ft gainWe began our hike at Kennard Trailhead, which is easy to miss if you aren’t looking for it. The approximate GPS address is 596 New Boston Road, Bedford, NH, though in reality the parking area is about 0.2 miles west of the junction of New Boston Rd and Esther Drive.These trails are very well mai...Read more