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.
August 2026
A Spartan obstacle course weekend at Badminton Estate on Aug 16 2026 offering Sprint 5 km, Super 10K, Beast 21K and a kids race for spectators.
A timed, flexible run along a 3.28 mile out and back route beside the Stroud Waterways canal. Runners choose distances from 5 km up to ultra and may complete as many laps as they wish within a seven hour limit.
Join the Crook Peak Cake Race in Axbridge on Wed 19 Aug 2026 for a spirited 3 mile fell challenge across stunning Somerset hills, finishing with cake and community cheer. On the day entry available for runners aged 14 and up.
A 9.8 km traverse near Pontypool with a 291 m climb, junior race distances and three-person team entries.
September 2026
A new 15 mile trail event in September 2026 on the Rhymney Valley Ridgeway Walk, with 2,267 ft of ascent, mostly off-road terrain, one fully stocked checkpoint and organised entry support from Rudry to Parc Penalta.
Races at Westonbirt Arboretum offer a 1 Mile fun run, 5 km, 10 km and half marathon on solid forest paths with on-course feed stations and event medals.
A riverside running festival on 6 September 2026 with 10 km, 5 km and a family fun run. Chip timing on multi terrain routes, canicross options, basic on site facilities and medals for all finishers.
A small community trail race in Epney, Gloucestershire covering about 10 miles along the canal towpath and local footpaths, with marshals and one aid station.
Run as far as you like at Alice in Runderland, a timed multi lap event at Parc Taf Bargoed with flexible start times and on course support. Choose from one lap up to marathon and earn a bespoke finisher medal.
A long, non-commercial fell race in the Black Mountains with a 27.4 km route and 1586 m of ascent. The event uses five checkpoints, requires full navigational kit, and operates on open access land with no on-course water provided.
A 12 hour Backyard Ultra on a 4.2 mile loop near Crickhowell in the Black Mountains. The final lap is run in reverse as a sprint to decide male and female winners; medals are awarded for 32 miles or more.
A five-lap ultramarathon in Berkeley, Gloucestershire across 25-27 September 2026, covering about 130 miles and 15,000 ft of ascent with a 24 hour cut off and 120 places, organized from Hamfields Leisure with camping and tracking included.
Guto Nyth Bran is a fell race on 26 September 2026 at Bedwas Community Hall covering 9.6 km with 396 m of climb. The course is partially marked, includes a short walk from parking, and is for entrants over 18.