Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 137 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A fell race near Machen covering 7 km with 365 m ascent, held with on the day entry and registration at Machen Welfare Ground.
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 small community trail race in Epney, Gloucestershire covering about 10 miles along the canal towpath and local footpaths, with marshals and one aid station.
Timed lap event at Parc Taf Bargoed on 12 September 2026 offering distances from 5 km up to ultra with a 7 hour time limit.
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.
A fell running race in Caerphilly on 26 September 2026 featuring a 9.5 km course with 336 m of climb, partially marked and with a short walk from parking to the start.
A trails half marathon through the Forest of Dean on 27 September 2026, organised by the Rotary Club with way-marked routes, chip timing and proceeds to charity.
A coastal 10 km race along the North Somerset shoreline, passing Black Nore Lighthouse and Redcliffe Bay. The mixed terrain route includes grass, mud, rocks and tarmac with undulating sections and a seafront finish.
October 2026
A chip timed 10 km trail race on 4 October 2026 through Somerset countryside, passing a prehistoric long barrow. The event includes a bespoke medal, Race Nation app support, camping nearby and proceeds shared with two charities.
Trail running and ruck options at Ashton Court Estate with 6k, 10k and half marathon distances and supplied GORUCK backpacks.
New off road 10 km along the River Wye near Ross on Wye on 4 October 2026, featuring wildlife, nearby facilities, £14.99 entry and a finisher medal.