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
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
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
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
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
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
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
Blue Hills, Milton, Massachusetts
The Blue Hills Reservation is one of the premiere mountain biking areas in Eastern Massachusetts because of its extensive trail system and varied terrain. Bordered by six cities and towns, the reservation encompasses about 7,... trails.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