Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 135 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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 24 hour trail ultra in Berkeley, Gloucestershire of about 130 miles across five roughly 26 mile laps with about 15,000 ft of ascent.
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 measured forest trail half marathon in late September with way-marked, marshalled routes, water stations, chip and gun timing, medals for finishers and trophies for category winners.
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 and ruck event at Ashton Court Estate on Oct 4, 2026 offering 6k, 10k and half marathon distances with Pro and Open categories 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.
Seven consecutive offroad race days at Pengethley Manor from 19 to 25 October 2026 with a seven hour time limit each day and distances from 5k to ultra. Each day awards a unique Halloween themed medal and a virtual option is available.