Join The Best Buddies Challenge. The 100, 55, and 20-mile rides start from different locations, and all end up at Hyannisport on Cape Cod. Each route takes riders along scenic, country roads to Hyannis Port. All rides are fully supported, with rest stops along the way and support vehicles on the road. Rental bikes are also available.… Continue reading Best Buddies Challenge, Cape Cod, MAY 30, 2026
Location: Wells Reserve at Laudholm, 342 Laudholm Farms Road, Wells, ME, 04090 Routes: 100 miles 63 miles 30 miles 2018 63-mile route Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
The Tour de Heifer’s 60 and 30-mile challenge routes follow dirt roads with minimal pavement. Both entail significant elevation change — that is, hill-climbing, and lots of it! All of the routes begin and end at Lilac Ridge Farm in West Brattleboro, VT. 2016 routes are shown: 60 miles Route at RideWithGPS View and print cue sheet… Continue reading Tour de Heifer, Brattleboro VT
The Vermont Gran Fondo is a non-competitive ride through Vermont’s Green Mountains. This ride will test your fitness with its challenging climbs. There are amazing views at the top of each gap—savor them for a moment before you speed downhill. This ride will resume in 2027. 2019 location: Bristol Recreation Club, 110 Airport Drive, Bristol,… Continue reading Vermont Gran Fondo, Bristol VT, 2027
The Maine Lobster Ride supports the Bicycle Coalition of Maine's work to improve bicycling in Maine. Start from Rockland District High School. Rockland District High School, 400 Broadway, Rockland, ME. Visit Bike Maine for more information. The ride will be held in late July 2026. Route at RideWithGPS View and print cue sheet View and… Continue reading Maine Lobster Roll, Rockland ME, July, 2026
Ride through beautiful Tiverton and Little Compton RI, with a barbecue upon return. All proceeds benefit the Megan L Cordeiro Memorial Foundation.
Join us for the Bikes Fighting Cancer FUNdraising bike ride in Western Mass, dedicated to supporting families dealing with the burden of a cancer diagnosis and advancing cancer research. Two beautiful routes start at the very cool Tree House Brewing Company and meander through the picturesque Pioneer Valley and along the Connecticut River, featuring long… Continue reading Bikes Fighting Cancer, Deerfield, MA, June 20, 2026
Start location: Light House Point Park, New Haven, CT Cue sheets 10 Mile Cue Sheet 25 Mile Cue Sheet 50 Miler Cue Sheet RideWithGPS 50 MILER: 48.4 mi 2,249 ft elevation 10 MILER: 10.4 mi 341 ft elevation
Stow Bike for the Woods supports the Stow Conservation Trust in Stow, MA. The shorter rides are fairly flat, while the longer rides passing through Harvard, Littleton, Hudson, Marlborough, and Stow are more hilly. 14-mile route: Map Directions 28-mile route: Map Directions 46-mile route: Map Directions 65-mile route: Map Directions 19 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS &… Continue reading Stow MA Bike for the Woods, August 9, 2025
Bicycles Battling Cancer is a fully supported one-day bike ride in support of the American Cancer Society. Every year, we have hundreds of riders sign up and fundraise for our mission to save lives, celebrate lives, and lead the fight for a world without cancer. Riders of all levels are encouraged to join and can… Continue reading Bicycles Battling Cancer, Lancaster MA, September 21, 2025
Wheeling for Healing Ride, Walk, Run for Cancer Care at Baystate Health - Join us 5/18/25! Wheeling for Healing is a fundraising event where participants can cycle their choice of a 10, 25, or 50-mile route, or walk/run the 5K route. All funds raised support cancer care and services at Baystate Health. We will once… Continue reading Wheeling for Healing, S. Deerfield MA, May 18, 2025
Bike Ride & Beer Festival 2026 departs from CISCO BREWERS in New Bedford, MA Choose your challenge from a 15, 30, or 45-mile ride through the beautiful areas of trail and less-traveled roads surrounding South Coast Massachusetts, complete with morning fuel stations, fully marked routes, rest stops, and SAG support for all riding levels. Finish… Continue reading Bikes & Beers, New Bedford, MA June 27, 2026
Join the American Lung Association for the 43rd Annual Trek Across Maine, Northern New England’s premier fundraising cycling event. Choose the traditional three-day, 180-mile ride, our one-day gravel ride, or participate virtually from anywhere. The Trek begins and ends at beautiful Pineland Farms in New Gloucester, featuring rolling farmland, wooded landscapes, and stunning Maine scenery.… Continue reading Trek Across Maine,New Gloucester, June 18-20, 2027
EVENT: 20th Annual John E. Jackman Tour de Mansfield DATE: Saturday, June 7, 2025 LOCATION: Mansfield Community Center, 10 S. Eagleville Road, Storrs, CT 06268 FEE: $30 before June 4; $35 on/after June 5; Participants under 18 ride for free, but must be accompanied by an adult (registration required for all) DETAILS: Participants select from… Continue reading Tour de Mansfield CT: June 7, 2025
The Pan-Massachusetts Challenge is a Massachusetts-based bike-a-thon that raises more money for charity than any other single athletic fundraising event in the country. Held annually on the first weekend in August, the PMC raises funds for Dana-Farber Cancer Institute, a world leader in adult and pediatric cancer treatment and research. The PMC has 14 different… Continue reading Pan-Mass Challenge, August 1 & 2, 2026
Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
Ride options will include a 30 mile Plus (30+ miles), Metric Century Plus (60+ miles), or Century route (100 miles), with starting locations in Mashpee, Sandwich and Orleans
The annual Farm Ride starts from the University of Massachusetts in Amherst, MA, and offers two full days of cycling in Pioneer Valley farm country, taking beautiful back roads. Arrowed route options range from 15-100 miles and include rest stops and S.A.G. support. Visit the Farm Ride site. 100-mile route Route at RideWithGPS View and print cue… Continue reading Amherst Pioneer Valley Farm Ride, August 8-10, 2025
The King Challenge is a fundraising event for Krempels Center, a Portsmouth NH based nonprofit organization dedicated to improving the lives of people living with brain injury.
Going the Distance Bike Ride Fundraiser for the Brattleboro Boys and Girls Club, Vermont. This annual bike ride raises much-needed funds to support the Boys & Girls Club of Brattleboro. The road rides are 40, 60, or 75 miles in distance, supported by 2 rest areas (Turners Falls and Greenfield) as well as a support vehicle.… Continue reading Going the Distance Century, Brattleboro VT, October 4, 2025
