Breakheart Reservation
Breakheart Reservation is a 640-acre hardwood forest with jagged, rocky outcroppings, two fresh-water lakes, and a rambling section of the Saugus River. Seven rocky hills, over 200 feet high, provide vistas of Boston, ... bostoncentral.com
Middlesex Fells: Skyline Trail | Stoneham/medford/winchester ...
This hike, which loops the western side of the Fells, has some steep ascents to afford great views of Boston. This trail is located in the western section of the Fells. Marked with white blazes, it circles the Winchester Rese... trails.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
Callahan State Park
I parked at the North Entrance and started by taking the Backpacker Trail. I then took Pine Tree Trail and Bear Claw trail. I had a hard time finding my way back to the North Entrance because at times three trails would me... trailpeak.com
Lynn Woods | Lynn Massachusetts Hikes | Trails.com
At nearly 2200 acres, Lynn Woods Reservation is one of the largest municipal parks in the United States. The forest contains a variety of ponds, wetlands, swamps, streams, large glacial outcroppings, and rocky ledges. Wildlif... trails.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
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
Needham Fitness Cruise Ride | Eliot Massachusetts Road Bike...
Based on what is believed to be the longest consecutive running weekly group ride in all of Massachusetts (if not beyond), the Needham Fitness Cruise is built for cycling enjoyment. It has a convenient starting point just off... trails.com
Middlesex Fells
Nice park, close to the city. Some nice hiking with views of Boston. Mountain biking is limited to one marked loop. Bikers are urged not to deviate from this path due to the tenuous relationship between MTBers and some of ... trailpeak.com
Henson Creek Trail
This trail is just over 6 miles and seems to be maintained fairly well. It goes through woods and crosses some streets that can have somewhat heavy traffic at times. Some parts of it are a bit hilly and there are a few bli... dirtworld.com
Belmont To Walden Pond Cruise | Belmont Massachusetts Road...
John Allis, a three-time Olympian, mapped this route in 1972 by tracing the least busy roads leading west from Cambridge. You'll explore the near-rural suburbs of Lincoln, Sudbury, and Weston. Since you pass so many attractio... trails.com
Lynn Woods Reservation | Lynn Massachusetts Mountain Bike...
Lynn Woods can boast being the second largest municipally-owned park in the United States--the largest being Fairmount Park in Philadelphia. Convenient to both the city of Boston and its suburbs to the north and south, the pa... trails.com
Southwest Corridor Park
Southwest Corridor Park is a 3.9-mile linear park through the Boston neighborhoods of South End, Roxbury, and Jamaica Plain. A recreation and commuter route popular with walkers, runners, and cyclists, the corridor is a tr... traillink.com
Belmont Conservation
Great place to burn the lungs. The first half of the ride is pure uphill with some cool singletrack, rather well maintained. Keep on your way up until you hit the water tower and bear right. From there, you have access ... singletracks.com
Minuteman Bikeway | Arlington Massachusetts Rails-to-trails ...
The Minuteman Bikeway has it all. It?s close to Boston, it?s historic, it?s located in a lush and beautiful area, and it?s great for families. Its historical significance is of particular note. The trail closely approximates ... trails.com
Fresh Pond Loop
This is a paved walkway with more people and dogs than you can count. I'm posting this as a note to other riders that this barely qualifies as "biking." :) Very pretty, though, and wonderful for people either learning h... singletracks.com
Southwest Corridor Park | Boston Massachusetts...
Southwest Corridor Park is a 3.9-mile linear park through the Boston neighborhoods of South End, Roxbury, and Jamaica Plain. A recreation and commuter route popular with walkers, runners, and cyclists, the corridor is a trium... trails.com
South Shore-wompatuck State Park Ramble | Hull Massachusetts...
This ride begins at a popular swimming beach near Boston, next to a musical amusement ride, an antique carousel. Then it explores four of the oldest and most scenic towns gracing the Atlantic Ocean: Hull, Cohasset, Scituate, ... trails.com