Connecticut · Ride calendar

Cycling Events in Connecticut

Connecticut rewards riders who don’t need big country. The Litchfield Hills in the northwest are genuinely rugged, threaded with narrow lanes, stone walls, and dirt roads that stay quiet, and the autumn up there is worth planning a trip around.

Don’t mistake the small map for easy. The roads pitch up again and again rather than climbing anything long, so it’s the constant, punchy kind of tired. Winter shuts much of it down, which makes the good months feel precious.

1 upcoming event · 1 organized rides

Map © OpenStreetMap contributors.

By the numbers

Standouts in the State

The Connecticut events that stand out on the numbers alone: the soonest start, the lowest listed entry, and the most route options.

Rides by City in Connecticut

Soonest Rides in Connecticut

1 total

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 Connecticut

How many cycling events are coming up in Connecticut?

Connecticut has 1 upcoming listed event: Sickle Cell Disease Association of America, CT/ Michelle's House Walk. Run. Bike. in New Haven on Sat, September 26, 2026.

What does it cost to enter a ride in Connecticut?

Listed entry fees currently start at $25. Check each registration page for current fees and deadlines.

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