Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 136 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A backyard ultra in Bristol where runners complete a 4-mile loop every hour for six hours, aiming to finish as many loops as possible.
A 20 km multi terrain fell race across the Mendips with 420 m climb, varied terrain features and charity support; cupless event with water points and age category prizes.
A 9.6 km fell race with 485 m ascent near Abergavenny on 31 October 2026; full WFRA kit is required and parking at the pub is very limited.
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.
Approximately 7 mile multi-terrain race from Risca Leisure Centre to Twmbarlwm and back, with about 1000 ft ascent; entries listed via Entry Central.
A multi-terrain 12 km off-road race from Barton Farm Country Park with a river crossing, chip timing, prizes and team awards, raising funds for Alzheimer's Support.
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.
Night and day off road 5 km and 10 km trail races around the Bath Skyline, plus a daytime kids 500 m and a canicross wave, with marked routes and finish medals.
Timed lap event in Cardiff Bay offering flexible start times and distances from one 5.3 km lap up to multi lap ultra within a 7 hour limit.
A 60 lap run at Queen Square marking men’s mental health month and raising funds for Talk Club in Bristol.
A Movember charity run at Ashton Court Park offering 1.5k, 5k, 10k and half marathon options with chip timing, medals and headbands, mixed path and trail terrain, some hilly sections, and on course refreshments.
Trail races from Bath Racecourse with a two lap hilly half and a one lap Ultra 10km actual 12.45km, raising funds for local charities.
A 5.7 km fell race in Llanfoist with 485 m ascent, limited to 120 runners; entry fees £6/£4 and no entries on the day.
Lap-based timed event at Parc Taf Bargoed on 28 November 2026 offering flexible distances from a 5.3 km lap up to ultra, with medal and no medal entry options.
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.
Timed lap event at Rhydycar, Merthyr Tydfil on 29 November 2026 with distances from 5 km to ultra on a certified tarmac course.
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..