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.

Learn more about Top Trails

#1. Cape Cod Rail-Trail


Among the most scenic recreation trails in Massachusetts and a favorite with cyclists and day hikers, the Cape Cod Trail provides access to beaches, fresh water ponds, cranberry bogs and wild wetlands…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Harwich, MA - Birding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running - 26 miles Best Trail in ma - Click to view allBestBirding, Cross-Country Skiing, Fishing, Horseback Riding, Mountain Biking, Rail-Trails, Road Biking, Trail Running Trail - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#2. Minuteman Bikeway


The Minuteman Bikeway has it all. It’s close to Boston, it’s historic, it’s located in a lush and beautiful area, and it’s great for families. Its historical significance is of particular note. The tr…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Arlington, MA - Mountain Biking, Rail-Trails, Road Biking, Walking - 11 miles Best Trail in ma - Click to view allBestMountain Biking, Rail-Trails, Road Biking, Walking Trail - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#3. Cape Ann Cruise


This ride explores Boston's North Shore. The shorter 22-mile loop circles the rocky shores of Cape Ann, where fishermen's cottages and grand summer homes now share the ocean views. The route passes th…
From the guidebook "Best Bike Rides in New England"
Gloucester, MA - Road Biking - 36.4 miles Best Trail in ma - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#4. Norwottuck Rail-Trail


Historians believe that the Native Americans who first lived in the region named the area “Norwottuck,” meaning “in the midst of the river.”The rail line originated as a Massachusetts Central Railroad…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Northampton, MA - Cross-Country Skiing, Rail-Trails, Road Biking, Walking - 8.5 miles
Published by The Globe Pequot Press

#5. Belmont to Walden Pond Cruise


John Allis, a three-time Olympian, mapped this route in 1972 by tracing the least busy roads leading west from Cambridge. You'll explore the near-rural suburbs of Lincoln, Sudbury, and Weston. Since y…
From the guidebook "Best Bike Rides in New England"
Belmont, MA - Road Biking - 33 miles
Published by The Globe Pequot Press

#6. Falmouth Shining Sea Path


Enjoy the brilliant views of the Nantucket and Vineyard Sounds on this short trail connecting Falmouth and Woods Hole. Surface: Asphalt. Location: Barnstable County.…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Falmouth, MA - Cross-Country Skiing, Rail-Trails, Road Biking, Walking - 4 miles
Published by The Globe Pequot Press

#7. South Shore-Wompatuck State Park Ramble


This ride begins at a popular swimming beach near Boston, next to a musical amusement ride, an antique carousel. Then it explores four of the oldest and most scenic towns gracing the Atlantic Ocean: H…
From the guidebook "Best Bike Rides in New England"
Hull, MA - Road Biking - 26.6 miles
Published by The Globe Pequot Press

#8. Roundabout Rutland Cruise


Even though Rutland lies in the exact geographical center of Massachusetts, still no one knows about it. Which is precisely its appeal to cyclists. Mount Wachusett is a few miles northeast of this ri…
From the guidebook "Best Bike Rides in New England"
Paxton, MA - Road Biking - 38 miles
Published by The Globe Pequot Press

#9. Cranberry Country Cruise


This ride begins in historic Plymouth. Before exploring this town, though, the tour heads inland on sandy-shouldered roads for a rolling, 7-mile cruise through the largest state forest in eastern Mass…
From the guidebook "Best Bike Rides in New England"
Plymouth, MA - Road Biking - 47 miles
Published by The Globe Pequot Press

#10. Cape in a Day (or Two) Classic


Many cyclists in New England dream about riding from Boston to Cape Cod—it’s a fantasy trip, one they plan to do someday. For others, this tour is an annual event—thanks largely to the American Youth…
From the guidebook "Best Bike Rides in New England"
Boston, MA - Road Biking - 115 miles
Published by The Globe Pequot Press

#11. Lincoln to Great Brook Farm Ramble


Lincoln, near downtown Boston, is ideal for rides extending through a landscape of woods and fields, country cottages, and grand estates. Walden Pond, the Old North Bridge Historical Site and the Conc…
From the guidebook "Best Bike Rides in New England"
Lincoln, MA - Road Biking - 30.2 miles
Published by The Globe Pequot Press

#12. Amherst to Quabbin Reservation Challenge


In Central Massachusetts lies the vast Quabbin Reservoir. The reservoir is now the centerpiece of a large wilderness area, and the more than fifty islands that stud its surface are home to wild turkey…
From the guidebook "Best Bike Rides in New England"
Amherst, MA - Road Biking - 53 miles
Published by The Globe Pequot Press

#13. Mount Greylock Classic


In the Northwestern corner of Massachusetts, 3,500-foot-high Mount Greylock rises over North Adams and Williamstown. It is a rarity among New England Mountains in that a paved road crosses its highest…
From the guidebook "Best Bike Rides in New England"
Williamstown, MA - Road Biking - 37.2 miles
Published by The Globe Pequot Press

#14. Marblehead Rail-Trail


Marblehead is one of the nicest beach communities north of Boston. This trail forks in two directions. Both branches are pretty, and both eventually lead to the Atlantic Ocean. The charm of this trai…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Marblehead, MA - Cross-Country Skiing, Horseback Riding, Rail-Trails, Road Biking, Walking - 5 miles
Published by The Globe Pequot Press

#15. Hopkinton Cruise


This ride begins at the town green in Hopkinton, at the starting line for the world-famous Boston Marathon. Instead of following the busy streets the marathon takes, this ride heads south and west int…
From the guidebook "Best Bike Rides in New England"
Hopkinton, MA - Road Biking - 41.2 miles
Published by The Globe Pequot Press

#16. Southwest Corridor


This urban rail-trail takes you from downtown Boston to Jamaica Plain. It is used by bicyclists commuting to and from downtown and by outdoor enthusiasts looking for some fun in the sun near Boston.…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Boston, MA - Rail-Trails, Road Biking, Walking - 5 miles
Published by The Globe Pequot Press

#17. Great Barrington Cruise


The Great Barrington Cruise is adapted from the Great Josh Billings RunAground, a triathlon run every fall. This ride follows the triathlon's cycling course almost to Stockbridge. It then turns south…
From the guidebook "Best Bike Rides in New England"
Great Barrington, MA - Road Biking - 28.9 miles
Published by The Globe Pequot Press

#18. Martha's Vineyard: Two Tours


Martha's Vineyard remains an island 'retreat' for beachgoers and cyclists alike. Its roads wind through woodland and farms, past miles of white sand beaches, around millponds, inlets, and creeks. The…
From the guidebook "Best Bike Rides in New England"
Vineyard Haven, MA - Road Biking - 24.7 miles
Published by The Globe Pequot Press

#19. Cohasset Coastal Ramble Ride


The Cohasset Coastal Ramble explores the shoulder of land southeast of Boston where the coastline curves primarily from an east-west to a north-south direction. It is the first really nice stretch of…
From the guidebook "Road Biking Massachusetts"
Black Rock, MA - Road Biking - 26.8 miles
Published by Falcon Guides

#20. Monument Valley Ramble


Centering on the Housatonic River Valley, winding across its plain and rolling along the foothills this ride is virtually flat its entire first half, once you climb the initial mile-long hill. Passing…
From the guidebook "Best Bike Rides in New England"
Great Barrington, MA - Road Biking - 37 miles
Published by The Globe Pequot Press