Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 139 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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 miles trail race from Keynsham through rivers, woods and fields with two stream crossings, canicross places, medals for finishers and limited entries.
Community fundraiser in Box, Wiltshire featuring an 800 m Colour Run and a 5 km trail run, with chip timing for the 5 km and proceeds supporting Box Primary School.
Virtual event 19 to 25 October 2026 with 5k 10k half marathon marathon and ultra options plus seven themed Halloween medals.
Virtual Halloween race with 5k, 10k, half and full marathon options, worldwide participation, virtual bibs and themed medals for paid entrants.
A worldwide virtual Halloween run offering 5k, 10k, half, marathon and ultra options, with virtual bibs and paid-medal postage available to verified finishers.