Virginia · Ride calendar

Cycling Events in Chesterfield, Virginia

Upcoming cycling events in and near Chesterfield, Virginia: road, gravel, fondos and rides, with dates, entry fees, maps, and local bike shops.

2 upcoming events · more across Virginia

RoadGravelGran FondoCyclocrossOrganized RidesCharity Rides
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By the numbers

Standouts in Town

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

Soonest startAug 2Guts Gravel Glory (GGG )Chesterfield, VALowest listed entry$60Guts Gravel Glory (GGG )Chesterfield, VAMost route options3 routesGuts Gravel Glory (GGG )Chesterfield, VAFurthest outFeb 21Monster CrossChesterfield, VA
Sun, August 2, 2026 Guts Gravel Glory (GGG ) Chesterfield, VA 50 Miles36 Miles19 Miles From $60 View Event Sun, February 21, 2027 Monster Cross Chesterfield, VA 50 Miles25 Miles From $60 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 Chesterfield

How many cycling events are coming up in Chesterfield, VA?

Chesterfield, VA has 2 upcoming events listed, from Sun, August 2, 2026 through Sun, February 21, 2027. The next one is Guts Gravel Glory (GGG ) in Chesterfield.

What does it cost to enter a ride in Chesterfield, VA?

Listed entry fees currently start at $60. Check each registration page for current fees and deadlines.

When is the busiest month for cycling events in Chesterfield, VA?

August 2026 is currently the busiest month on the Chesterfield, VA calendar with 1 listed event.