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Cheltenham · United Kingdom

Cycling & running events in Cheltenham, 2026

599events this year

599 races within 80 km of Cheltenham

Road, trail, gravel, MTB — you name it, we've got it. Find something worth telling your friends about.

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Top events

A few races to know in Cheltenham

We all need a goal — why not think big? Pick one and start training for it. Already happened this year? Find some practice races to build toward next year's edition.
Run·Road
Cheltenham

Guy Fawkes 5

The Guy Fawkes 5 is a Tewkesbury race organized by Tewkesbury Running Club, named to coincide with Britain’s Bonfire Night season in early November. The event is part of the local running scene, not an elite-only setup; the club has over 100 members and attracts runners from Ledbury, Gloucester, Cheltenham, and Pershore. Tewkesbury Running Club was founded in the early 1980s. Its members compete locally and regionally, including in county championships and the Cotswold Way Relay, and some also participate in triathlons, duathlons, and ultras. The Guy Fawkes name refers to the Gunpowder Plot, when Guy Fawkes was apprehended guarding explosives under the House of Lords; the subsequent Bonfire Night tradition features bonfires, fireworks, and effigy customs around the same time of year.

Road
Run·Trail
Cheltenham

Maverick Cotswolds Trail Run

Maverick Cotswolds Trail Run.

Trail
Run·Multi-terrain
Cheltenham

Santa Fun Run 5k

Listed in our event index as Skipton Santa Fun Run 2026.

Multi-terrain
About cycling & running in Cheltenham

Cheltenham Training Notes

Running: Locals run the town centre when they want steady miles past Pittville Pump Room, Town Hall, and Montpellier Gardens. Montpellier Gardens, Benhall Park, Cox's Meadow, and the River Chelt keep easy Z2 days green and simple. Cheltenham Running and Walking Club gives runners a local base for sessions, routes, and race chatter. Run Cheltenham 10k and Half gives the town its proper road anchor. The route covers a 4km B-road stretch in one single loop. Cheltenham Running Festival sits on the calendar too, so locals never lack a target.

Cycling: Cheltenham & County Cycling Club is the main hub, and the vibe is social as much as cycling. The Saturday 40s leave the Pump Rooms at 9:00am, run about 40 miles, and come back by 12:30pm. 30am and averages 18+ mph over around 65 miles. The beginner ride is a 5-mile spin through parks and cycle paths. Cheltenham to Bishops Cleeve Cycle Path gets its anchor day with On Your Bike. Cleeve Hill gives the climbing, and club gravel rides mix Cotswold tracks, quiet roads, and occasional singletrack.

Season: Spring and summer suit Cheltenham best for base miles, intervals, and longer cafe-stop rides. The parks become so colorful, and locals mean it when they say it is so green and colourful. Summer keeps the town lively for early runs, evening spins, and steady laps through Charlton Kings, Shurdington, and Leckhampton. Winter changes the kit, the pace, and the planning. Winter Training Rides run from November to March and leave at 09.00. Runners still use the town centre paths and parks, but frost matters because a typical year records 35.5 air-frost nights.

Upcoming

Coming soon in Cheltenham

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
Popular elsewhere · next 30 days

What runners & riders are signing up for

If you're traveling — or just curious — here's where the action is across two of the most active markets on TrainerDay.