Massachusetts Cycling Events 2026β2027
Verified calendar of gravel races, centuries, gran fondos, and mountain bike events across Massachusetts.
All Massachusetts Events
Showing 8 verified eventsTree 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....
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....
Recommended Gear & Pacing Electronics for Massachusetts Rides
Proven pacing electronics, rear vehicular radar, and Italian protection curated for demanding endurance routes in Massachusetts.
Favero Assioma Power Pedals (Duo / Pro MX-2)
Precision pacing for long climbs. Β±1% power accuracy with instant ANT+/Bluetooth connectivity and 50-hour rechargeable battery.
Garmin Varia RTL515 Radar Tail Light
Rear radar awareness on rural and mountain roads. Detects approaching vehicles up to 153 yards back with cockpit alerts.
LAS Enigma / Cobalto Road Helmet
High-ventilation race protection. 24 high-flow air channels with micro-dial fit for all-day cooling on heated climbs.
Massachusetts Cycling Guide & Frequently Asked Questions
What are the premier or marquee cycling events in Massachusetts?
In Massachusetts, premier marquee monuments on the calendar include Pan-Mass Challenge, Deerfield Dirt Road Randonnee (D2R2). In total, Massachusetts currently features 8 verified events on the Threshold Cycling platform across gravel, road, mountain bike, and century ride disciplines.
When does the cycling and racing season peak in Massachusetts?
Based on verified event start dates, the Massachusetts cycling calendar reaches its peak in Oct with 6 scheduled events. Active racing and tours span throughout Oct, Jul, Aug. Riders can use the interactive month timeline above to filter events for specific training blocks.
What elevation gain and course profiles can I expect in Massachusetts?
Courses in Massachusetts with published vertical profiles average approximately 9,650 feet of elevation gain per event. The calendar includes high-altitude mountain challenges exceeding 6,000 feet of climbing alongside rolling courses under 3,000 feet. You can use the Climbing Vert filter above to match events to your climbing fitness.
How do I register for Massachusetts races or add events to my calendar?
Each listing in the Massachusetts directory links directly to official registration permalinks (such as BikeReg and BikeSignUp) or official race director websites. You can add any event directly to Google Calendar, Apple Calendar, or Outlook using the 1-click calendar export button, or subscribe to the MA State Calendar Feed in the header.