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. ...
Norwottuck Rail Trail (Francis P. Ryan Section) is a hiking and biking trail in Northampton, ...
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 ...
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 ...
Explore the wonderfully classic coastal New England town of Marblehead, cruising along ...
The heart of the Pioneer Valley, midway between the Connecticut and Vermont– New Hampshire ...
Ipswich ranks as one of the most beautiful towns in the state, both architecturally and ...
Ten miles north of New Bedford is a cluster of large, unspoiled lakes surrounded by woods, ...
Home to many accomplished Massachusetts cyclists, Foxboro and the surrounding towns offer ...
Weir Hill is a hiking and biking trail in North Andover, Massachusetts. It is 0.9 miles ...
The North Andover Ramble explores some of the most enjoyable cycling roads north of Boston. ...
Ashuwillticook Rail Trail is a hiking and biking trail in Berkshire County, Massachusetts. ...
The Shelburne Falls Challenge is not for the timid. With more than 4, 300 feet of climbing ...
Based on the popular In Search of the Llamas Charles River Wheelmen route, the Dover Cruise ...
The Newbury Ramble takes you exploring among the broad salt marshes, prosperous farmland, ...
This is no mere century ride—it’s an epic journey through central Massachusetts from historic ...
This is a tour of four classic New England communities northwest of Boston, and you’ll ...
Convenient to Boston, the South Shore Coastal Cruise explores the quiet, tree-lined streets ...
Load More