Cheltenham
Trail Running Calendar near Cheltenham 2026-2027
Explore the top trail runs near Cheltenham for 2026-2027! We've gathered 89 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Wild Run Cotswolds showcases rugged off road trails on a private estate with fully marked routes, chip timing and a family friendly supporter zone. Entries are limited to 600; choose 10K, half, marathon or the six hour 360 challenge.
Inflatable obstacle course in Cheltenham on 10 October 2026 offering 2.5k to 15k options, music zones, medals and family friendly participation rules.
A 55 km self navigated ultra through varied Forest of Dean terrain with GPX navigation, multiple aid stations, mandatory kit requirements and a separate canicross category.
An all-terrain race over the Malvern Hills on 10 October 2026, limited to 250 runners with a minimum age of 16 and pre-entry only.
Trail race in an Area of Outstanding Natural Beauty around Biblins Youth Campsite, Ross-on-Wye covering approximately 6 miles or 10k on mixed trails and single track. Entry is limited to 200 runners and prizes include individual and team awards.
Run or walk a 10km cross country route through the woods and village of Walton Hall with electronic timing and a finish line roll included.
A 5k night trail at Dunkertons Park in Cheltenham where runners use head torches to light the course. Open to ages 16 and over, with prizes for top three men and women and on-site refreshments and safety rules.
November 2026
A 10 mile off-road trail run in Stonehouse near Stroud on 1 November 2026, with an initial uphill mile, muddy undulating trails, a finisher medal and a 2 hour 30 minute cutoff.
Timed multi lap run at Coate Water Country Park with 3.28 mile laps, finishers receive a medal and the event supports the British Legion.
A ten mile cross country race in Chipping Sodbury with muddy, varied terrain and water obstacles. Held on Remembrance Sunday and preceded by a commemorative silence, it draws around 1300 runners.
Marathon and half marathon in Broadway, Worcestershire on 15 November 2026, featuring mostly trail terrain, marked routes and a waiting list.
A 6.5 mile multi-terrain off-road race at Croome Park on 22 November 2026, limited to 350 entries, with medals and goodie bags for all finishers.
A new out and back 10 km along the River Wye in Hereford on 28 November 2026, mainly off road with a bespoke finisher medal and post-race refreshments.
December 2026
Part of a 12 Days of Christmas series at Pengethley Manor in Ross on Wye offering 5k, 10k, half marathon, marathon and ultra distances on a tough off road loop. Runners and walkers have seven hours to complete their chosen distance with virtual optio..
A festive 5 km off road run at Tinkley Gate National Trust on 6 December 2026 raising funds for Allsorts, with fancy dress welcome, dogs on short leads and on site parking.
A 12-day consecutive running challenge at Pengethley Manor, Ross-on-Wye, with daily choices from 5k to ultra on a 2.5 km lap offroad course. Each day has a unique medal and there are in-person and virtual entry options.
Part of a themed Christmas series at Pengethley Manor, this offroad event offers distances from 5k to ultra with a seven hour completion limit and both on site and virtual entry options.
Part of a 12-day Christmas race series at Pengethley Manor, offering 5k, 10k, half, marathon and ultra options on a 2.5 km lap off-road course. Walkers and runners have a seven hour time limit and paid entries receive a medal.