Massachusetts · Ride calendar

Cycling Events in Boston, Massachusetts

Boston rewards riders who learn its maze. The Minuteman Bikeway and river paths thread the metro car-free, the Blue Hills offer punchy climbs close in, and New England’s fierce cyclocross culture fills the fall calendar.

Traffic and old, tangled roads are the price of admission, so route knowledge matters here. But the region rides hard and deep, winter drives people to the trainer or the cross course, and autumn is the reward everyone waits for.

1 upcoming event · more across Massachusetts

Map © OpenStreetMap contributors.

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Bike Shops in Boston

The easiest way to a start line is a shop that knows your bike. These Boston shops are listed free — addresses, websites, and phone numbers included.

Browse all Boston bike shops →

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 Boston

How many cycling events are coming up in Boston, MA?

Boston, MA has 1 upcoming listed event: BBF Pan Mass Challenge Team 2026 in Boston on Sat, August 1, 2026.

What does it cost to enter a ride in Boston, MA?

Listed entry fees currently start at $0. Check each registration page for current fees and deadlines.