Massachusetts Cycling Events 2026β2027
Verified calendar of gravel races, centuries, gran fondos, and mountain bike events across Massachusetts.
All Massachusetts Events
Showing 30 verified eventsFreetown 50
Official registered mtb event in Assonet, MA. Direct registration on BikeReg....
South Beach CX #3
Official registered cyclocross event in Westwood, MA. Direct registration on BikeReg....
Snackroads Ride to Benefit Tommy's Place
Official registered road race event in Centerville, MA. Direct registration on BikeReg....
2026 Tour de Greenbelt
Official registered gravel event in Essex, MA. Direct registration on BikeReg....
Kilowatt Cross (RVCX Series #3)
Official registered gravel event in Northfield, MA. Direct registration on BikeReg....
Autumn Escape Gravel
Official registered gravel event in Sandwich, MA. Direct registration on BikeReg....
South Beach CX #4
Official registered cyclocross event in Westwood, MA. Direct registration on BikeReg....
BOSSCROSS - Westford, MA
Official registered cyclocross event in Westford, MA. Direct registration on BikeReg....
Berkshire Cross
Official registered cyclocross event in Great Barrington, MA. Direct registration on BikeReg....
West Valley Fall Orchard Tour
Official registered local tour event in Westhampton, MA. Direct registration on BikeReg....
2026 Greylock Go Around 50K Mountain Bike Fundraiser
Official registered mtb event in Adams, MA. Direct registration on BikeReg....
Great Pumpkin Smash
Official registered mtb event in Westwood, MA. Direct registration on BikeReg....
Henry Ar Foon Celebration Ride
Official registered local tour event in Hingham, MA. Direct registration on BikeReg....
10th Annual Tour de Falmouth
Official registered local tour event in Falmouth, MA. Direct registration on BikeReg....
Fall Foliage Gravel Grinder (F2G2)
Official registered gravel event in Great Barrington, MA. Direct registration on BikeReg....
King's Tour of the Quabbin
Official registered gravel event in Hardwick, MA. Direct registration on BikeReg....
South Beach CX #5
Official registered cyclocross event in Westwood, MA. Direct registration on BikeReg....
Lancaster CX Festival - Lanterns & Legions p/b Midnight Ride & Minuteman CX
Official registered cyclocross event in Lancaster, MA. Direct registration on BikeReg....
Great River Ride Century / Berkshire Brevets 2026
Official registered gravel event in Westfield, MA. Direct registration on BikeReg....
South Beach CX #6
Official registered cyclocross event in Westwood, MA. Direct registration on BikeReg....
Tree House CX
Official registered cyclocross event in South Deerfield, MA. Direct registration on BikeReg....
CRW Cranberry Harvest Century
Official registered century event in Plymouth, MA. Direct registration on BikeReg....
Really Rad Festival of Cyclocross 2026
Official registered cyclocross event in Falmouth, MA. Direct registration on BikeReg....
Brutiful Cape: Gravel Bike & Fat Bike Adventure Rides - Oct 24 & 100 Miles for Fat Bikes Oct 25
Official registered gravel event in Eastham, MA. Direct registration on BikeReg....
Cycling-The Series + Partially Canceled
Official registered gravel event in West Yarmouth, MA. Direct registration on BikeReg....
Cider Cross
Official registered cyclocross event in Phillipston, MA. Direct registration on BikeReg....
NCF Batacular Bike Race 2026
Official registered cycling event in Nantucket, MA. Direct registration on BikeSignUp....
35th Annual Cycle-Smart Northampton Cyclocross
Official registered cyclocross event in Northampton, MA. Direct registration on BikeReg....
Pan-Mass Challenge
The single largest athletic fundraising event in the country riding from Sturbridge to Provincetown....
Deerfield Dirt Road Randonnee (D2R2)
The quintessential New England dirt road randonnee tackling brutal Franklin County gap climbs....