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
Middlesex Fells
For many years Middlesex Fells has been a very popular spot for Boston area mountain bikers and hikers. "The Fells" is just 7 miles north of downtown Boston and offers exceptional trails. Mountain biking is allowed at the ... 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 Woods Reservation is the second largest municipal park in the greater Boston area. This 2,200 acre forest reserve consists of ponds, wetlands, streams, deciduous/evergreen forest and rocky ledge. The ponds provide... bostoncentral.com
Horn Pond
This 102 acre raised natural great pond is located a half-mile south of Woburn Center. Maximum depth is 40 feet; average depth 10 feet. Transparency (in summer at least) is only fair at six feet. Aquatic vegetation is scan... anglerweb.com
Marblehead Rail-trail
Shaped like a Y, this 4.1-mile rail-trail connects two seaside towns. From the trail junction in quaint Marblehead, one branch meanders through conservation areas and past harbor overlooks to Salem, notorious for its 1692 ... traillink.com
Charles River Bikeway
The Charles River Bike Path (AKA The Dr. Paul Dudley White Bicycle Path) is designed for human-powered use, such as cycling, running, rollerblading, strolling, etc. The path follows the banks of the Charles River, and make... trailpeak.com
Lynn Woods Reservation, Lynn, Massachusetts
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
Minuteman Bikeway
The Minuteman Bikeway is a paved pathway exclusively for bikers, joggers, and in-line skaters, that partially overlaps the route that Paul Revere rode during his famous jaunt. It's ends are in Cambridge and Bedford, althou... trailpeak.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
Castle Island
Castle Island is a unique 22 acre park that goes along Dorchester Bay. Not exactly rugged singletrack or challenging hiking, but the long walking/biking trail snakes around Castle Island is a beautiful, serene trip that is... trailpeak.com
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
Circle Boston, Boston, Massachusetts
As you start this ride form the Boston Public Library, stop to appreciate its importance. Established in 1854, it has the distinction of being the first free public library in the United States. Boston, on the other hand, ope... trails.com
Brooksby Farm
Brooksby Farm is an 275-acre working farm, managed by the City of Peabody. Brooksby Farm is a fun place to visit almost any time of the year. Pick your own fruits including strawberries in June, blueberries and raspber... bostoncentral.com
Charles River Loop
There is a 15 paved loop that runs next to the Charles river from downtown out to Watertown. For mos of the way there is a dirt path running along side it. Great early season training rides or for a quick spin when you ... singletracks.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
Middlesex Fells Reservation
The Fells offers a ton of variety in its biking, but to really capture it, you need to do the 8-mile mountain bike loop that goes all the way around the reservation. This has lots of gravely fire road, rocky and rooted ... singletracks.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