Links to over 100 bicycle trails and bike paths from the Berkshires to the North Shore and Cape Cod.
Massachusetts Bicycle Trails
Category: Massachusetts
Waltham MA Ride
Start Location: 200 West St, Waltham, MA Routes & Maps: Metric Ride: View course map, import Map My Ride GPS, or import waypoints 40 mile : View course map, import Map My Ride GPS, or import waypoints 25 mile: View course map, import Map My Ride GPS, or import waypoints 10 mile: View course map, import waypoints, or import full route GPS coordinates Route… Continue reading Waltham MA Ride
River Valley Ice Cream Ride
Start location: Turners Falls, MA Description: The River Valley Ice Cream Ride blends the best of summertime fun – bikes, gorgeous roads, and ice cream. Three routes ranging from 10 to 50 miles offer great cycling for a range of riding abilities. Kiddie Scoop Loop seven (7) miles along the Canal Side Rail Trail in beautiful… Continue reading River Valley Ice Cream Ride
Rodman Ride for Kids, Foxboro, MA, May 16, 2026
The Rodman Ride for Kids is a 25, 50, and 100-mile non-competitive cycling fundraiser for at-risk children in Massachusetts and the youth-focused social-service agencies that serve them, agencies such as Big Brothers Big Sisters of Cape Cod and the Islands. The affiliated agencies raise funds through corporate sponsorships and ridership and are matched at a… Continue reading Rodman Ride for Kids, Foxboro, MA, May 16, 2026
Ride to Defeat ALS, Wayland, MA, September 19, 2026
The ALS Association Massachusetts Chapter hosts its Annual “Ride to Defeat ALS."
Autumn Escape Trek, Sandwich, MA, September 25-27, 2026
The American Lung Association Autumn Escape Bike Trek is an annual one, two, or three-day tour of Cape Cod after the summer season has passed, and is supported by more than 100 volunteers both at the start and finish lines and along the route at rest stops and intersections. Location: Camp Burgess, Sandwich, MA view on map Beneficiary: American Lung Association http://www.lung.org… Continue reading Autumn Escape Trek, Sandwich, MA, September 25-27, 2026
Will Bike 4 Food: Hatfield MA, September 20, 2026
WB4F is a non-competitive ride through the beautiful Pioneer Valley to raise funds for The Food Bank of Western MA. The ride has four routes to choose from: 10, 25, 50, or 100 miles, beginning and ending at the Lions Club Pavilion, Billings Way, Hatfield MA. The ride will be followed with a fun after-party… Continue reading Will Bike 4 Food: Hatfield MA, September 20, 2026
Great River Ride, Westfield, MA
Starting from Westfield near the Mass Turnpike in western Massachusetts, the Great River Ride is "one of the best century rides in the USA" according to Bicycling Magazine. With almost 9000 ft of climbing over its 102-mile course, the Great River Ride is one of the most challenging centuries in New England. View and download… Continue reading Great River Ride, Westfield, MA
Cycle for Shelter, Haverhill MA, September 13, 2026
The annual Cycle for Shelter to benefit Emmaus will be held at Northern Essex Community College. Cyclists can ride a 20-mile, 40-mile, 62-mile or 100-mile scenic route that will take them through Haverhill, MA, up to the seacoast of New Hampshire, and south through the North Shore of Massachusetts. Upon returning to the college, riders can… Continue reading Cycle for Shelter, Haverhill MA, September 13, 2026
Deerfield Dirt Road Randonnée, August 22, 2026
The Deerfield Dirt Road Randonnée (D2R2) was conceived in the 1990’s as just a favorite dirt-road loop in the hilltowns of Franklin County, Massachusetts. Since its birth as an organized ride 11 years ago, many have hailed D2R2 as the hardest, most beautiful, most fun, most traffic-free, most unique and overall best ride that they… Continue reading Deerfield Dirt Road Randonnée, August 22, 2026
Ride to defeat ALS, Wayland MA, September 19, 2026
Ride to Defeat ALS is a community fundraising event that creates the hope and action needed to create a world without this devastating disease. Each ride brings together a diverse group of individuals and teams dedicated to taking the challenge for those who bravely fight ALS and creates hope for a future without it. Riders… Continue reading Ride to defeat ALS, Wayland MA, September 19, 2026
Lexington MA Tour de Cure, August 16, 2026
Tour de Cure is the American Diabetes Association’s premier cycling event for all ages and abilities. All the routes will be fully supported with bike mechanics, volunteer ride ambassadors, rest stops with food and water, cheering volunteers, and more. Our post-ride festival includes lunch, music, games, a Beer Garden, and a Wellness Expo. Join the… Continue reading Lexington MA Tour de Cure, August 16, 2026
Habitat for Homes, Sandwich MA, September 13, 2026
5K to 40 Mile Scenic Routes. All ages and levels are welcome to join! Choose from 3 BIKE routes – 14, 20, or 50 miles. Choose to RUN or WALK a 5K or 10K along the Cape Cod Canal BikewayStart and end for all routes is at the US Coast Guard Station Cape Cod Canal… Continue reading Habitat for Homes, Sandwich MA, September 13, 2026
Friendship Tour, Whitinsville, MA, Saturday, June 6, 2026
Event: 41st Annual Valley Friendship Tour Location: Ride starts/ends at Alternatives Whitin Mill, 50 Douglas Rd. Whitinsville, MA Participants are invited to walk, jog or ride through the Blackstone Valley on one of three non-competitive routes: 30-Mile cycling route (9am), a 5K walk/run (10am), or a Golden Mile walk (11am). The variety of routes means that people of all… Continue reading Friendship Tour, Whitinsville, MA, Saturday, June 6, 2026
Snackroads Ride to Benefit Tommy’s Place, Sat. Sept. 26, 2026
4th ANNUAL SNACKROADS RIDE TO BENEFIT TOMMY'S PLACE: September 26, 2026 Registration includes custom event swag, Ride with GPS turn-by-turn voice navigation, stocked aid station and post-race party. EVENT SWAG: Need to register 6 weeks prior to event to guarantee you'll get swag POST RACE PARTY: Stay tuned for more details ROUTE NAVIGATION: All registered riders… Continue reading Snackroads Ride to Benefit Tommy’s Place, Sat. Sept. 26, 2026
Greenville Tri-State half century
This is the 52-mile version of Narragansett Bay Wheelmen's Tri-State Century Start: Apple Valley Mall, Greenville, RI (map to start) Description: Challenging ride in undeveloped countryside touching on Rhode Island, Connecticut and Massachusetts. Route at RideWithGPSView and print cue sheet View and print map & cue sheetGPX fileTCX Course
Wenham MA Chebacco Woods mountain biking
Gordon College in Wenham Massachusetts has an excellent trail network for hiking and mountain biking connecting to the other well-maintained trails in adjoining Chebacco Woods. The easy trails wrap around several ponds and are appropriate for beginner and intermediate cyclists, with gently rolling terrain through hemlock and beech forests surrounded by glacial outcroppings. Not shown… Continue reading Wenham MA Chebacco Woods mountain biking
Hatfield MA, Connecticut River Valley Century
Start: Lion's Pavilion, Billings Way, Hatfield, Massachusetts Ride: Pioneer Valley Freewheelers century ride Description: This bicycle ride follows rural town roads and lightly traveled state highways . The first half heads north to Brattleboro, Vermont parallel to the Connecticut River then returns along the east side of the river. Just a few hills, and great… Continue reading Hatfield MA, Connecticut River Valley Century
Sudbury Century Ride
Route: This ride starts in Sudbury MA. Starting Location: Lincoln Sudbury Regional High School, 390 Lincoln Rd, Sudbury MA. Route at RideWithGPSView and print cue sheet View and print map & cue sheetGPX fileTCX Course
Unon CT – Brimfield MA Antiques Ride
This is the Narragansett Bay Wheelmen's Brimfield Antique Ride, 34 miles from Union Connecticut. Start: Public library or church, downtown Union CT. (map to start). Park at the white church on right at the green in the center of Union, Ct. Description: Starting from Union, this ride circuits four towns, passing an area of rugged,… Continue reading Unon CT – Brimfield MA Antiques Ride
Cycling New England 