How many cycling events are coming up in Massachusetts?
Massachusetts has 4 upcoming events listed, from Sat, August 1, 2026 through Sat, September 19, 2026. The next one is BBF Pan Mass Challenge Team 2026 in Boston.
Massachusetts · Ride calendar
Cycling Events in Massachusetts
Massachusetts gives you two riding worlds. West in the Berkshires the roads climb long and wooded through hill towns, while out on Cape Cod it flattens to sandy, breezy lanes and one of the best rail trails in the Northeast.
In between it’s classic New England: stone walls, short punchy climbs, and traffic you learn to route around. Fall is the headline act, and winter sends most people indoors for a stretch.
4 upcoming events · 4 organized rides
By the numbers
Standouts in the State
The Massachusetts events that stand out on the numbers alone: the soonest start, the lowest listed entry, and the most route options.
Rides by City in Massachusetts
Soonest Rides in Massachusetts
4 total Sat, August 1, 2026 BBF Pan Mass Challenge Team 2026 Boston, MA Free entry listed View Event Sat, August 8, 2026 Bikes & Beers Newburyport Newburyport, MA From $28.5 View Event Sun, August 9, 2026 KINETIC RIDE Lawrence, MA From $50 View Event Sat, September 19, 2026 Live Like Scott Event Hampden, MA Free entry listed View Event
How we build these listings: Event counts, dates, and fees are computed from live registration listings (synced nationally from the RunSignup/BikeSignup platform), deduplicated and filtered to cycling disciplines. We list what is verifiably open for registration — not every ride that exists. Last updated July 19, 2026.
Common Questions About Riding in Massachusetts
What does it cost to enter a ride in Massachusetts?
Listed entry fees currently run from $0 to $50, depending on the event and route. Check each registration page for current fees and deadlines.
When is the busiest month for cycling events in Massachusetts?
August 2026 is currently the busiest month on the Massachusetts calendar with 3 listed events.
Riding Somewhere Else?
Every state, every event, or a straight search by name and city.