Cycling Events in the State of Massachusetts.
February 2026-
Feb 12 Crank It Up at Broken Records
Boston, MA
Special Event
Feb 22 Winterräden
Uxbridge, MA
4 laps, 3 laps, 2 laps
Mountain Bike Fat Bike
March 2026-
Aug 30, 2025 - Mar 9, 2026 Major Taylor jerseys, caps, posters
Worcester, MA
Special Event
Mar 21 Berkshire Brevet Series St. Pat's 100K Populaire
Westfield, MA
100 km
Recreational Gran Fondo
Mar 28 Berkshire Highlands Pentathlon ~Run~Ride~Paddle~Adventure Run~Summit Hike & Ski/Board Descent~
Charlemont, MA
Multisport
April 2026-
Apr 11 2026 Berkshire Brevet Spring 200K
Westfield, MA
200 km
Recreational Gran Fondo
Apr 12 The Mix Tape
Fall River, MA
50 miles, 6 hours
Gravel Mountain Bike
Apr 26 Secret Squirrel MTB
Taunton, MA
6 miles, 4.5 miles, 18 miles, 12 miles, 5 hours, 4 hours, 3 hours
Mountain Bike NEBRA
May 2026-
Feb 12 Crank It Up at Broken Records
Boston, MA
Special Event
Feb 22 Winterräden
Uxbridge, MA
4 laps, 3 laps, 2 laps
Mountain Bike Fat Bike
March 2026-
Aug 30, 2025 - Mar 9, 2026 Major Taylor jerseys, caps, posters
Worcester, MA
Special Event
Mar 21 Berkshire Brevet Series St. Pat's 100K Populaire
Westfield, MA
100 km
Recreational Gran Fondo
Mar 28 Berkshire Highlands Pentathlon ~Run~Ride~Paddle~Adventure Run~Summit Hike & Ski/Board Descent~
Charlemont, MA
Multisport
April 2026-
Apr 11 2026 Berkshire Brevet Spring 200K
Westfield, MA
200 km
Recreational Gran Fondo
Apr 12 The Mix Tape
Fall River, MA
50 miles, 6 hours
Gravel Mountain Bike
Apr 26 Secret Squirrel MTB
Taunton, MA
6 miles, 4.5 miles, 18 miles, 12 miles, 5 hours, 4 hours, 3 hours
Mountain Bike NEBRA
May 2026-
Saturday, May 2, 2026 Bike MS: Ride the Vineyard
Cycling event website: https://events.nationalmssociety.org/2504
Cycling event is for/about: National Multiple Sclerosis Society
Cycling event categories: Route Distances: 25, 45 and 60 miles
Cycling event location- Oak Bluffs, Martha's Vineyard
Cycling event website: https://events.nationalmssociety.org/2504
Cycling event is for/about: National Multiple Sclerosis Society
Cycling event categories: Route Distances: 25, 45 and 60 miles
Cycling event location- Oak Bluffs, Martha's Vineyard
May 9 Massochistah (aka The Spurty Dirty Hurty Gurty) Fundraiser For Youth and Adaptive Cycling
Ashfield, MA
70 miles, 50 miles, 30 miles, 20 miles, 0 miles
Gravel Recreational
Ashfield, MA
70 miles, 50 miles, 30 miles, 20 miles, 0 miles
Gravel Recreational
May 12 2026 - Somerville Community Bike Ride 5:00pm - 6:30pm.
Cycling Event Website: https://www.boyntonunionconnect.com/slow-roll
Cycling event is for/about: Build cycling confidence for beginners with a community focus.
Cycling event categories: Casual ride.
Cycling event location- 550 Somerville Ave, Somerville, MA 02143
Register For Somerville Community Bike Ride Here!
May 16 Second Annual Paul Revere’s Bike Ride for the Concord Museum
Concord, MA
32.4 miles, 21.3 miles
Recreational
May 17 Final de Barro
Westwood, MA
4 laps, 3 laps, 2 laps, 1 laps
Mountain Bike
June 2026-
Jun 11-13 2026 Patriot Half: Volunteer Registration
East Freetown, MA
Multisport
Jan 2 - Jun 15 2026 Cape Cod Cycling Club Sponsorship
Hyannis, MA
Special Event
Jun 20 The BIKES FIGHT CANCER Charity Ride
Deerfield, MA
Recreational
Jun 20 B2VT TRAINING RIDES AND CLINICS
Lexington, MA
90-100 miles, 80 miles, 60 miles, 40 miles
Special Event
Jun 20 Volunteer - 40th Annual OutRiders Boston to Provincetown Bike Ride
Boston, MA
Recreational
Jun 20 2026 B2VT RIDE
Bedford, MA
60 miles, 149 miles, 106 miles
Bike Tour Recreational
Jun 20 40th Annual OutRiders Boston to Provincetown Bike Ride
Boston, MA
128 miles
Recreational
Jun 28 Carolina Hill MTB Classic 2026
Marshfield, MA
3 laps, 2 laps, 12 laps, 1 laps
Mountain Bike
July 2026-
Jul 5 DomnarskiFarm.com 2026
Ware, MA
100 miles, 6 hours
Mountain Bike Fat Bike Special Event
August 2026-
August 1, 2026 - August 2, 2026 - Pan-Mass Challenge 2026
Cycling event website: https://www.pmc.org
Cycling event is for/about: The Pan-Mass 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 route combinations, ranging from 25 to 177 miles, for riders to choose from.
Riders can choose from three locations:
- The College of The Holy Cross: 1 College St, Worcester, MA 01610
- Babson College: 231 Forest Street, Wellesley, MA 02457
- Massachusetts Maritime Academy: 101 Academy Dr, Buzzards Bay, MA 02532
Riders may ride on Saturday, Sunday, or both days. On Saturday, riders start in either Wellesley or Worcester and finish in Bourne. On Sunday, riders may start in Bourne or Wellesley; finish lines are in Provincetown and Wellesley.
Cost of event varies by route ($125 - $275).
Fundraising commitments vary by route ($2000 - $6000), due by October 1st
Cycling event categories: Non-profit, fundraising, charity, Marathon, Bike-a-thon
Please register to ride on PMC website: https://www.pmc.org
PMC Facebook page: https://www.facebook.com/PanMassChallenge
Aug 9 Cycle Against Suicide Pilgrim Tour
Plymouth, MA
85 miles
Bike Tour
Aug 2 2D2R2 2026
Greenfield, MA
35 miles, 12 miles, 80 km, 180 km, 160 km, 100 km
Gravel Recreational
September 2026-
Sep 10-12 Beyond the Bike - 25th Anniversary Ride
Needham, MA
250 miles
Special Event
Sep 12 Ride-to-Remember - 25th Anniversary 911 Memorial Ride - Springfield, MA to Hartford, CT 75-mile Loop
Springfield, MA
75 miles
Recreational Special Event Gran Fondo
Sep 13 Ride for Homes
Sandwich, MA
50 miles, 20 miles, 14 miles, 5 km, 10 km
Special Event Recreational
Sep 13 Second Summer Cycle
Yarmouth, MA
60 miles, 34 miles, 15 miles, 101 miles
Gran Fondo
Plymouth, MA
85 miles
Bike Tour
Aug 2 2D2R2 2026
Greenfield, MA
35 miles, 12 miles, 80 km, 180 km, 160 km, 100 km
Gravel Recreational
September 2026-
Sep 10-12 Beyond the Bike - 25th Anniversary Ride
Needham, MA
250 miles
Special Event
Sep 12 Ride-to-Remember - 25th Anniversary 911 Memorial Ride - Springfield, MA to Hartford, CT 75-mile Loop
Springfield, MA
75 miles
Recreational Special Event Gran Fondo
Sep 13 Ride for Homes
Sandwich, MA
50 miles, 20 miles, 14 miles, 5 km, 10 km
Special Event Recreational
Sep 13 Second Summer Cycle
Yarmouth, MA
60 miles, 34 miles, 15 miles, 101 miles
Gran Fondo
September 25, 26 and 27, 2026 Autumn Escape Bike Trek
Cycling event website: https://cycleforair.lung.org/aebt
Cycling event is for/about: Fund raising for the American Lung Association programs
Cycling event categories: Road Riding, Gravel Ride, Charity
Cycling event location- Massachusetts/ Sandwich/Cape Cod
Facebook page Here!
Register Here!
October 2026-
October 3rd, 2026 - PMC Unpaved 2026 (9:00AM - 9:00PM)
Cycling event website: https://www.unpaved.org/ride/experience/event-schedule
Cycling event is for/about: PMC Unpaved is a charitable gravel cycling experience that takes place in the Berkshires of Massachusetts each fall, hosted by the Pan-Mass Challenge. As another ‘spoke in the wheel’ of the organization’s yearly fundraising campaign, PMC Unpaved brings together hundreds of new and existing PMC riders for the ultimate gravel ride and camp experience to raise money for Dana-Farber Cancer Institute. 100 percent of every rider-raised dollar goes directly to support critical cancer research and care at Dana-Farber.
Now in its fifth year, PMC Unpaved includes three routes: 20-, 30-, and 50-mile options, known as “The Owl,” “The Raven,” and “The Eagle,” respectively. Immediately after the ride, the PMC Unpaved camp experience continues with live entertainment, activities for riders and their loved ones, and a speaking program featuring PMC leadership and members of the PMC Living Proof® community, a special group of riders and volunteers who have faced, or are currently facing, cancer diagnoses.
Cycling event categories: Gravel, Outdoors, Community,
Cycling event location: Camp Mah-Kee-Nac; 6 Hawthorne Rd., Lenox, MA, 01240
Additional comments about event: Registration: $200
Minimum Fundraising Commitment: $2,300 (due by November 1, 2026)
Oct 11 Cycling, the Series
Cotuit, MA
47.5 miles, 47.5 miles
Gran Fondo
November 2026-
Nov 21 Secret Squirrel CX
Raynham, MA
2 laps, 45 minutes, 40 minutes, 30 minutes, 20 minutes, 4 hours, 3 hours, 2 hours
Cyclocross Mountain Bike
Jan 2 - Nov 30, 2026 2026 NEBC Club Membership
Burlington, MA
Club Membership
December 2026-
Dec 5 The Ice Weasels Cometh
Southwick, MA
48 minutes, 45 minutes, 40 minutes, 25 minutes
Cyclocross Fat Bike
Jan 1 - Dec 31, 2026 Rippers 2026 Membership
Winchester, MA
Club Membership
Jan 1 - Dec 31, 2026 NVP 2026 Membership and Waiver
Acton, MA
Club Membership
Jan 1 - Dec 31, 2026 2026 Minuteman Road Club Membership
Boston and Metrowest, MA
Club Membership
Jan 2 - Dec 31, 2026 2026 Cape Cod Cycling Club Annual Membership
Hyannis, MA
Club Membership
Jan 8 - Dec 31, 2026 2026 New England Bicycle Racing Association (NEBRA) Club & Event Director Membership
Harvard, MA
Club Membership NEBRA
Jan 22 - Dec 31, 2026 Blue Hills Cycling Club Membership 2026
Milton, MA
Club Membership
Cotuit, MA
47.5 miles, 47.5 miles
Gran Fondo
November 2026-
Nov 21 Secret Squirrel CX
Raynham, MA
2 laps, 45 minutes, 40 minutes, 30 minutes, 20 minutes, 4 hours, 3 hours, 2 hours
Cyclocross Mountain Bike
Jan 2 - Nov 30, 2026 2026 NEBC Club Membership
Burlington, MA
Club Membership
December 2026-
Dec 5 The Ice Weasels Cometh
Southwick, MA
48 minutes, 45 minutes, 40 minutes, 25 minutes
Cyclocross Fat Bike
Jan 1 - Dec 31, 2026 Rippers 2026 Membership
Winchester, MA
Club Membership
Jan 1 - Dec 31, 2026 NVP 2026 Membership and Waiver
Acton, MA
Club Membership
Jan 1 - Dec 31, 2026 2026 Minuteman Road Club Membership
Boston and Metrowest, MA
Club Membership
Jan 2 - Dec 31, 2026 2026 Cape Cod Cycling Club Annual Membership
Hyannis, MA
Club Membership
Jan 8 - Dec 31, 2026 2026 New England Bicycle Racing Association (NEBRA) Club & Event Director Membership
Harvard, MA
Club Membership NEBRA
Jan 22 - Dec 31, 2026 Blue Hills Cycling Club Membership 2026
Milton, MA
Club Membership
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