Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 139 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2027
A 5 km fell race with 220 m of climb at White Hart in Axbridge on 18 August 2027, with on the day entry for £10 and FRA insurance.
Timed multi lap event at Brimscombe Port using a 2.62 mile canal loop, with flexible start window, medal option, and distances from one lap to ultra within a seven hour limit.
A 35-mile trail ultramarathon on 29 August 2027 from Chepstow Castle along the Wye Valley Trail and Offas Dyke, returning through the Tiddenham Tunnel with live music at the finish.
September 2027
Races at Westonbirt Arboretum include a half marathon, 10 km, 5 km and 1 mile fun run on largely flat stone forest paths with medals and feed stations.
An annual non-commercial 27.4 km fell race in the Black Mountains with five checkpoints, full kit required and online entry via Fabian4.
A 12 hour Backyard Ultra on a 4.2 mile mixed trail and tarmac loop near Crickhowell, with a reverse-direction final lap to decide male and female winners.
A team relay across the Black Mountains near the Brecon Beacons of about 50 km, with teams of 5 to 10 choosing their own route and handovers.
Timed lapped ultra on a 5 mile woodland loop at Westonbirt Arboretum with 3, 6, 9 and 12 hour solo or team options, aid stations and on-site recovery support.
A five lap ultramarathon around Berkeley Gloucestershire covering roughly 130 miles and 15,000 ft gain with limited entry and proceeds to local charity.
Autumn Half Marathon on way marked Forest of Dean trails with water stations, chip timing, medals for finishers and proceeds supporting local charities.
October 2027
A roughly 12 miles mostly trail race in Keynsham with two stream crossings. Race HQ is The New Inn and parking is at East Car Park.
A self navigated 55 km trail ultra from Beechenhurst through the Forest of Dean with about 1,300 m of climb, four aid stations, medical support and a canicross category.
November 2027
An 11 mile trail run from Stonehouse Town FC on the edge of the Cotswolds with water stations, notable climbs and a canicross category.
February 2028
A point to point 30 mile ultra along the Severn Path from Travelodge Stonehouse to Severn Beach. The course is mostly flat with two checkpoints, mandatory kit requirements, non refundable entry and finishers receive a bespoke medal and MTC head visor..