Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 133 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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 rucking at Ashton Court Estate with 6km, 10km and half marathon options and GORUCK backpacks provided.
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.
A 55 km forest ultra on 10 October 2026 at Beechenhurst, featuring technical single track, open river stretches, on-course aid and a separate canicross category.
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.
Off-road family races on 11 October 2026 at Withymead Playing Fields with 2 km, 5 km and 11 km options, organised to raise funds for Marshfield Primary School PTA.
Join the Aberfan Memorial Run in Merthyr Tydfil to honour the 1966 victims and support the Aberfan Memorial Charity. Choose 5 km to ultra on a scenic tarmac loop along the Taff Trail with flexible start times and official timing.
A 12.5 mile trail race from Keynsham on 18 October 2026 featuring rivers, woods, two stream crossings, canicross places and medals for every finisher.
Family friendly 5k Trail Run and 800 m Colour Run at Box Recreation Ground raising funds for Box Primary School with colour stations and chip timing.