Best Road Biking in Massachusetts

This list represents the most popular road biking in Massachusetts. Use this list to plan your next Massachusetts road biking trip. Select a state and/or activity below to find even more top trails.

Cape Cod Rail Trail is a hiking and biking trail in Barnstable County, Massachusetts. ...
This ride explores Boston's North Shore. The shorter 22-mile loop circles the rocky shores ...
John Allis, a three-time Olympian, mapped this route in 1972 by tracing the least busy ...
Enjoy the brilliant views of the Nantucket and Vineyard Sounds on this short trail connecting ...
This ride begins at a popular swimming beach near Boston, next to a musical amusement ...
Even though Rutland lies in the exact geographical center of Massachusetts, still no one ...
This ride begins in historic Plymouth. Before exploring this town, though, the tour heads ...
In the Northwestern corner of Massachusetts, 3,500-foot-high Mount Greylock rises over ...
Many cyclists in New England dream about riding from Boston to Cape Cod—it’s a fantasy ...
Lincoln, near downtown Boston, is ideal for rides extending through a landscape of woods ...
Norwottuck Rail Trail (Francis P. Ryan Section) is a hiking and biking trail in Northampton, ...
This ride begins at the town green in Hopkinton, at the starting line for the world-famous ...
This urban rail-trail takes you from downtown Boston to Jamaica Plain. It is used by bicyclists ...
The Great Barrington Cruise is adapted from the Great Josh Billings RunAground, a triathlon ...
Bald Hill Road is a hiking, biking, and horse trail in Boxford, Massachusetts. It is within ...
Minuteman Bikeway is a hiking and biking trail in Middlesex County, Massachusetts. It ...
Martha's Vineyard remains an island 'retreat' for beachgoers and cyclists alike. Its roads ...
Harold Parker Road is a hiking, biking, and horse trail in Essex County, Massachusetts. ...
The Cohasset Coastal Ramble explores the shoulder of land southeast of Boston where the ...
Centering on the Housatonic River Valley, winding across its plain and rolling along the ...
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