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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Dartmouth, Massachusetts
Hike Frank Knowles–Little River Reserve Trail
4.64 mi / 295 ft gainFrank Knowles-Little River Reserve contains nearly 9 miles of hiking trails to explore. Start off by parking in the white sea shell parking lot. From there you will find the trail marked by a DNRT sign . My group and I walked along the red/boardwalk trail which features a number of boardwalks lea...Read more -
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 -
Boston, Massachusetts
Run the Arnold Arboretum Trail
5.02.6 mi / 150 ft gainPark in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and summer is overwhelmingly green. There are dozens of ...Read more -
Chilmark, Massachusetts
Menemsha Hills Reservation Loop
5.02.98 mi / 344 ft gainGPS service in densely wooded areas on the Vineyard is hard to come by, so plugging in Menemsha Hills Reservation before getting on the road is advised. Traveling down N Road, you'll find an unmarked gravel road located between Turtle Cove and Trustees Lane. A short 400 meter drive will take you ...Read more -
Westport, Massachusetts
Hike Gooseberry Island
1.5 mi / 36 ft gainBegin an hour before sunset at the intersection between West Beach and East Beach Road. The intersecting roads will lead you to a paved causeway over the ocean. Waves typically clash on either side of you as you drive over the ocean. There is a free parking lot once you reach the opening. To reac...Read more -
Ashland, Massachusetts
Hike the Ashland Reservoir Trail
5.03.2 mi / 68 ft gainPark in the lot on State Park Road (see map) to access the trail. It's a popular trail that is dog-friendly. Pay attention to the trail as at parts it is not well marked.Read more -
Williamstown, Massachusetts
Mount Greylock via Money Brook Trail
9.57 mi / 2849.96 ft gainPark in the parking lot on Hopper Rd. Walk to the end of the road where you will find the Hopper Trailhead. Take the right fork. The Money Brook trail will take you to a waterfall, the Mt. Greylock summit, and back to the end of Hopper Rd. The trail is long but worth the hike, exploring parts of ...Read more -
Acton, Massachusetts
Hike the Pratt's Brook Conservation Area Loop
4.01.5 mi / 85 ft gainPark in the small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4545482, -71.4358192. The loop is very diverse wit...Read more -
Randolph, Massachusetts
Hike the Ponkapoag Pond Trail
4.03.82 mi / 173 ft gainPark at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round.Read more -
Harvard, Massachusetts
Hike along the Nashua River and the Oxbow National Wildlife Refuge
9.5 mi / 0 ft gainPark in the lot on Tank Road to access the Nashua River Trail. Keep your eyes peeled for turtles, chipmunks, birds, and other wildlife! This trail is open from April to October. The trail can become flooded and muddy after a rain/ snow, so for a shorter alternative to the 9.5 miles, you can take...Read more -
Provincetown, Massachusetts
Explore Hatches Harbor and Race Point
5.03.3 miHatches Harbor & Race Point Lighthouse trail is not super long or difficult. Pretty straight forward, at least up to Hatches Harbor. There is a small parking lot that fits about six cars off Province Lands Rd. I think we had a good amount of rain leading up to that day and the trail reflect...Read more -
Savoy, Massachusetts
Tannery Falls Loop
0.54 mi / 135 ft gainThe hike to Tannery Falls may be a little confusing, I'll clear it up for you before you even go there! To get to The falls you will travel down a dirt road that isn't very well maintained during the winter. As you keep driving down the dirt road you will notice a pond , which means you are almos...Read more -
Truro, Massachusetts
Hike the Pamet Area Trail
1.9 miPamet Area Trail is in Truro, towards the ocean within the Cape Cod National Seashore. As we were driving to the parking area it felt like it was wrong, as it often does. There was a dead end and school signs, which are for the N.E.E.D. Academy (apparently also doubles as a hostel during the su...Read more -
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 -
Wellesley, Massachusetts
Walk along Lake Waban
3 miNote: The campus is currently closed due to COVID-19 restrictions. This is a lake on Wellesley College Campus. It is easy to get to from just about any direction. Just park and walk toward the lake, and there are paths that will take you there. The easiest place to park (pinned on the map) is ju...Read more -
Marlborough, Massachusetts
Hemingway Street Trail
1.73 mi / 197 ft gainHemingway Street Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Marlborough, Massachusetts.Read more