Berkshires to Boston bicycle tour
Berkshires to Boston
Category: Massachusetts
Lexington, MA 22-Mile Ride
START/FINISH LOCATION: Lexington High School, 251 Waltham Street, Lexington, MA 02421 Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
Charles River Wheelmen Fall Century 2017
This Charles River Wheelmen century ride offers 100, 62, and 50 miles through Groton, Pepperell, and Dunstable. The full century continues on back roads to Lunenberg then north along the Souhegan River to Wilton, NH, and back through Brookline, NH. Start Littleton, MA 100 miles Route at RideWithGPS View and print cue sheet View and print… Continue reading Charles River Wheelmen Fall Century 2017
Massachusetts-New Hampshire 200K
This route is provided by New England Randonneurs, starting from Lexington, MA Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
Massachusetts Formidable Ride
The Formidable is the toughest road ride in Massachusetts, with three routes: a 160-mile pavé ride, a century version, and a mixed-terrain ride. The Pavé 160 Mile and Pavé 100 Mile rides start at the Ride Studio Cafe, Lexington, MA. The 120-mile mixed terrain Terra Dirt Ride starts in West Brookfield, MA. 160-mile Pave' Ride View route at RideWithGPS View and print cue sheet… Continue reading Massachusetts Formidable Ride
Coastal Trails Newburyport, MA
The Coastal Trails Network is a 30-mile, public system of bicycle and pedestrian trails linking the unique coastal features, town centers, neighborhoods and transportation hubs in the communities of Amesbury, Newbury, Newburyport and Salisbury, Massachusetts.
Bruce Freeman Trail
The Bruce Freeman Trail goes through the communities of Lowell, Chelmsford, Westford, Carlisle, Acton, Concord, Sudbury, and Framingham in Massachusetts -- following the 25-mile route of the old New Haven Railroad Framingham & Lowell line.. Download a PDF version of the map Download a Trail Brochure PDF
Lexington MA Century
This ride is from the annual Mass Bike Summer Century in 2011, starting from Lexington High School, 251 Waltham Street, Lexington, MA map. Route at RideWithGPSView and print cue sheet View and print map & cue sheetLog in to RideWithGPS & click on More to export GPS files
Bar Harbor to Boston
This 5-day, 390-mile route takes advantage of the best cycling in Maine, New Hampshire, and Massachusetts along the North Atlantic's scenic coastline. Bar Harbor Loop Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files Day 1: Bar Harbor to Hope Route… Continue reading Bar Harbor to Boston
Minuteman Ride, Concord, MA
The former MS Minuteman Ride visits the beautiful roads of historic Concord and the surrounding towns west of Boston. The ride has been discontinued 60 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files 25 miles Route at RideWithGPS View and print cue sheet… Continue reading Minuteman Ride, Concord, MA
Great Barrington, MA -Philmont, NY Loop
60-mile ride Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
AMC Boston Bike Committee Rides
AMC FG 2015-Lake Luzerne 45 Mile Ride Washington County, NY 45.1 AMC Rally 15 Mile Concord, MA 15.8 AMC Rally 16 mile ride Concord, MA 15.9 AMC Rally 29 Mile Concord, MA 29.0 AMC Boston 67 Mile Rally Ride 2013 Harvard, MA 67.4 AMC Exploring Woodstock CT Woodstock, CT 33.4 AMC FG 2015-Fort Ann Cross… Continue reading AMC Boston Bike Committee Rides
Western MA Tour
This 233-mile tour rolls through western Massachusetts and southern Vermont. Route at RideWithGPS View and print cue sheet View and print the mapLog in to RideWithGPS & click on More to export GPS files
First Responder Ride, Boston to NYC, September 6-10, 2026
The First Responder Ride for Resilience is a five-day Boston to New York City bicycle ride on the 25th anniversary of 9/11, honoring the 343 first responders who gave their lives. This cycling experience benefits Livestrong, Friends of Firefighters, and the Boston Fire Cancer Foundation, raising funds for the thousands more who continue to face higher rates of cancer and mental… Continue reading First Responder Ride, Boston to NYC, September 6-10, 2026
Salem, MA – Marblehead loop
Start location: Salem Commuter Rail Station. Description: 23-mile loop. Visit historic Salem and Marblehead on the Massachusetts North Shore, with great views of the Atlantic. Heavy traffic. Includes the unpaved Marblehead Bike Trail. Route at RideWithGPSView and print cue sheet
Tour de Barnstable, MA, May 31, 2026
This is the 5th year benefit ride though all 7 villages of Barnstable MA, 38 miles on June 9, 2019. Go to https://tourdebarnstable.com/
Pain in the Mass, Amherst MA
THE PAIN in the MASS TOUR was designed to help support The Tyler Foundation and the families affected by epilepsy.
Boston to Provincetown, MA
Start: Northeastern University, Boston, MA. This is the 125-mile former Harbor to the Bay fundraising ride. PDF Cue Sheet Route at RideWithGPS View and print cue sheet View and print the mapLog in to RideWithGPS & click on More to export GPS files
Ride for Angels, North Andover MA
Ride For Angels takes you through Northeast MA and Southern NH portions of New England to raise funds and awareness of Angel Flight NE's mission. All of the donations given on behalf of these “Road Angels” will benefit Angel Flight NE.
Vineyard Warrior Triathlon
Start: State Beach, Oak Bluffs, Massachusetts Bike route: Oak Bluffs north via Beach Road to Tisbury. Tisbury along State Road to West Tisbury. West Tisbury along Edgartown-Tisbury Road to Edgartown. Edgartown along Edgartown-Oak Bluffs Road to Oak Bluffs. Challenge: Ascend Sysiphus' climb. 2017 route Route at RideWithGPSView and print cue sheet View and print mapLog… Continue reading Vineyard Warrior Triathlon
Cycling New England 