Best Trail Running in Massachusetts

Trying to find the best trail running in Massachusetts? Bivy has great hiking, biking, paddling, climbing, skiing, riding and more, with hand-curated trail maps, as well as detailed driving directions.

1

Massachusetts, Hampshire County

02 :16 hrs
4.8 mi
213.07938 ft
Hard

Beautiful views of the Pioneer Valley. It can be strenuous at times but is fairly easy. It combines the orange trail and the white trail.

2

Connecticut, Middlesex County

01 :49 hrs
7.1 mi
89.24954 ft
Hard

Millers Pond State Park is a heavily wooded and beautiful park. Mountain biking here is excellent, but difficult; the trail is also used for hiking so be aware. Be apprised that the area is hunted, so it will be important to know when the hunting dates are. Millers Pond is another feature of this adventure and is excellent for trout and smallmouth bass fishing, for any interested.

3

Massachusetts, North Adams

02 :33 hrs
5.8 mi
345.51617 ft
Hard

The majority of this trail is at a high point, as it follows the ridge, providing great views for the duration of most of the hike. Mt. Greylock’s peak is the highest point in Massachusetts and the views are phenomenal. Following the Old Summit Road on the way back down provides a change in scenery and brings you near the Money Brook Falls which can be easily accessed via Hopper Trail.

4

Rhode Island, Kent County

01 :30 hrs
4.2 mi
33.606216 ft
Moderate

Wickaboxet Management Area is a pristine and natural area, thick with forest. The trail is not well known so you will likely enjoy seclusion, which adds to the allure of the hike. The forest is full of different tree species, including ash, birch, maple, pine and oak. Wildlife that you may see along the trail include deer, raccoon, small critters and birds. One of the highlights of the trail is Rattlesnake ledge. Be apprised that the area is hunted, so during hunting season you will need to dress appropriately to be safe.

5

Massachusetts, Princeton

01 :34 hrs
3.7 mi
175.32635 ft
Moderate

Wachusett Mountain is the highest peak in Massachusetts, east of the Berkshires and is famous for its Fall foliage. From the summit there are great views of Boston, Mt. Monadnock in New Hampshire, and much of Central and Eastern Massachusetts. You will traverse the east side of the mountain, reach the summit, and loop around the base of the mountain back to where you started. The trails are well-marked narrow hiking paths.

6

Rhode Island, Washington County

01 :54 hrs
5.5 mi
24.803938 ft
Moderate

The trail through Great Swamp Management Area (one of the largest freshwater swamps in the region) run through wet-land and upland woods, fields, and along vegetated and open waters. The habitats near the pond harbor frogs, kingfisher, pond turtles and osprey. Be apprised that only leashed dogs are permitted on this trail. Also, be aware that you will want to wear fluorescent orange during October-February, which is hunting season.

7

Rhode Island, Newport County

00 :51 hrs
2.5 mi
8.781045 ft
Easy

The features of this trail along the jagged rocky Sauchest Point include views overlooking Sachuest Bay, open waters of the Rhode Island Sound, the mouth of the Sakonnet River and wildlife. Wildlife that you may see include hawks, snowy owls, migrating osprey, swallows, an occasional harbor seal and other bird species. Be apprised that dogs must be kept on a leash while in the refuge. Also, be aware of poison ivy and biting insects.

8

Massachusetts, Saugus

01 :00 hrs
2.8 mi
34.60313 ft
Moderate

This loop explores many of the major features of Breakheart Reservation’s 640-acre hardwood forest including the well preserved natural habitat, two lakes, and views of Boston’s skyscrapers in the distance. The path will take you up some rocky hills which will display beautiful views of Silver Lake and Pearce Lake. There are places along the shores of these lakes to sit on the beach and enjoy nature’s beauty.

9

Connecticut, Middlesex County

01 :19 hrs
3.3 mi
114.7125 ft
Moderate

Located in the town of East Hampton Hurd State Park (land purchased by the state in 1914) offers with hiking, picnicking, and mountain biking. This hiking adventure features Carlson Pond, spectacular river and valley views from ridges on White Mountain, as well as the Connecticut River. The Connecticut River offers good fishing too. Be apprised that dogs must be kept on a leash while in the state park and there is a parking fee.

10

Massachusetts, North Adams

03 :33 hrs
7.7 mi
641.396 ft
Hard

Henry Thoreau was a famous American author and naturalist who wrote a book, “A Week on the Concord and Merrimack Rivers” as he travelled from Concord, MA to Concord, NH. This trail journeys through some of the same area that Thoreau did and he wrote about in this book. You will start out on Bellows Pipe Trail, make a steep incline to meet up with the Appalachian Trail and walk along the ridge displaying beautiful views until you reach Mt. Greylock Summit, the highest peak in Massachusetts.

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