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
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
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
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
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
Minuteman Bikeway
You won't get lonely on the Minuteman Bikeway. The 11-mile rail-trail through suburban Boston is one of New England's most popular trails. Warm summer weekends in particular bring folks of all ages and abilities elbow to e... traillink.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
Alewife Linear Park/somerville Community Path
Alewife Linear Park is a beautiful paved trail stretching 2 miles east from the Alewife T-station in Cambridge to Cedar Street in Somerville. The park came about after the Massachusetts Bay Transportation Authority (the "T... traillink.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
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
Cape In A Day (Or Two) Classic, Boston, Massachusetts
Many cyclists in New England dream about riding from Boston to Cape Cod. For all but the most experienced riders this a challenge best tackled in a group. To make it easier Massachusetts designated certain roads as the offici... trails.com
Cape In A Day Classic Ride, Dorchester Heights, Massachusetts
An ambitious double-metric century ride from downtown Boston to the very tip of Cape Cod, the Cape in a Day Classic is not for the fainthearted. The only "one-way" ride in this book, you must plan carefully to tackle this one... 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
Alewife Linear Park / Somerville Community Path, Boston,...
Alewife Linear Park is a beautiful paved trail stretching 2 miles east from the Alewife Tstation in Cambridge to Cedar Street in Somerville. The park came about after the Massachusetts Bay Transportation Authority put its Red... trails.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