Rocky Woods
The reservation features over six miles of former woods roads and footpaths through rolling hills of white pine and red oak that are part of both the Neponset River Watershed and the Charles River Watershed. Rocky ledges a... trailpeak.com
Cutler Park
The parking area for Cutler Park is located in Needham MA. But the park itself extends into Dedham, Newton, Brookline and Boston. The park consists of a few hills and a lot of trails near an 800-acre marsh along the Charle... trailpeak.com
Needham Town Forest, Needham, Massachusetts
shorter and less technical than most of the rides in this area, the Needham Town Forest loop is perfect for riders just breaking into the sport. The trails within the 200-odd-acre park run the gamut from plain-Jane fire roads... trails.com
Blue Hills State Reservation
Located only minutes from the bustle of downtown Boston, the Blue Hills Reservation stretches over 7,000 acres from Quincy to Dedham, Milton to Randolph, providing a green oasis in an urban environment. Rising above th... bostoncentral.com
Noanet Woodlands
The appeal of the Noanet Woodlands is the view from the top of Noanet Peak. You'll be hard pressed to find a vista that conceals nearby suburbia so well this close to Boston. This unique rock-top can be found by Caryl Trai... trailpeak.com
Millenium Park
This is one of the best places to walk your dog in Boston. The folks here are real laid back and there are dogs running free everywhere. You can also take the path into the woods for some bird watching or just to get away ... trailpeak.com
Strawberry Hill Trail
Strawberry Hill Trail is the longest, most well maintained section of trail for all the above activities. This trail is part of Hale Reservation in Westwood and Dover, Mass. Hale is a non-profit organization that facilitat... trailpeak.com
Francis William Bird Park
Francis William Bird Park is an 89-acre landscaped park created and endowed in 1925 by Charles Sumner Bird, Sr. and his wife Anna in memory of their eldest son, Francis William Bird (1881-1918). Over three miles of wal... bostoncentral.com
Hammond Pond
So much to do in this space just outside of Boston!!! Some great bouldering, nice easy mntn biking, trails to run or walk, and a nice spot to throw your boat into!! Directions: From 9 east or west to the Hammond Pond Parkw... trailpeak.com
F. Gilbert Hills State Forest, Foxboro, Massachusetts
The town of Foxboro, 35 miles southwest of Boston. Although the terrain here is relatively flat, there are many regular short climbs and descents. Some of the single-track trails can be difficult-less-experienced riders shoul... trails.com
Cutler Lake
A small lake in Cutler Park, Needham. The seven hundred acres known as Cutler Park comprise the largest remaining fresh water marsh on the middle Charles. Located in Needham and Dedham, the marsh and small lake attract ove... anglerweb.com
Weston Conservation Land
Miles of winding single track through wetlands, over rocks and roots. Some stream crossings and bridges for those looking for technical challenge. Not too tough overall. Great place for Intermediate riders to bring their b... dirtworld.com
Adams Farm
Trail maps are available at trailhead. Singletracks are found throughout off main fire road. Some sweet fast singletrack available. Hilly trail along power lines. Nothing too technical, just some fast singletrack and cl... singletracks.com
Blue Hills Ski Area
This ski area is kind of a hidden gem. This place is great for two groups of people. It is great for beginners or a family starting out. The prices are cheaper than some of the closer major resorts and the hill is not as s... trailpeak.com
Walpole Loop
Lots of double track with some single track and one small fireroad section. Also, the trail runs IN a stream for about 100 yards so unless you are VERY good, get ready to get wet. dirtworld.com
Ashland State Park
A beach, lots of wooded trails. Lots of dogs off leash, especially when walking through the woods and over the "dam". Great way to meet lots of dogs along your walk, unleashed. Directions: Rte. 495 to exit 21A to Rte. 135 ... ecoanimal.com
Borderlands State Park
An Excellent mandering walk through one of the most scenic state parks in Massachusetts! And best of all, one of the top 10 Disc Golf Courses in the country! Directions: From north: Take Rte. 128 south to Rte. 95 south (to... trailpeak.com