Trail Running calendar near Chepstow 2025-2026
We have found 333 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.
We have found 333 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.
Enjoy a scenic off road 9.5 km trail around Kinver Edge and the Rock Houses, run as two laps over tracks and trails. Limited to 100 runners, the event includes medals, finish goodies and prizes for the top three in each category.
Take on the Sorbrook Slog on 22 February 2026, a lively 7 mile multi terrain race through footpaths, fields and gullies around Sorbrook and Sluvad in Cwmbran. Enjoy marshals on course, post race tea and cake and a finishers goodie bag.
The Terminator 2026 is a tough but rewarding 12 mile trail race around Pewsey, Wiltshire, mostly off road with muddy climbs and high point views. All finishers receive a unique T shirt and race village treats await.
Castle 2 Castle Ultra is a 32 mile ultramarathon from Powis Estate to Caffi Wylfa, taking runners over fast paths and rolling footpaths with scenic castle views. Finishers get a celebratory plate and goodies and top three men and women win..
Tackle the 25 mile South Shropshire Circular from Minsterley Village Hall, a navigational challenge across scenic hills with checkpoints and a 10 hour limit. Organised by LDWA and currently full with a waiting list.
Run the scenic Brecon to Cardiff Ultra, a fully marked 70 km one way race along the Taff Trail on 1 March 2026. Enjoy epic views, checkpoint support and a finishers medal as you cross the line at Coleg y Cymoedd in Nantgarw.
Run the Weymouth Bay 10K on 1 March 2026 along a mostly flat, measured seaside course from Bowleaze Cove to Pleasure Pier. Entries open for 15 plus with on day registration and proceeds support Margaret Green Animal Rescue.
Tackle the Imber Ultra, a scenic 33.5 mile multi terrain trail run around the Imber Range on Salisbury Plain, starting in Westbury. Organised as a charity fundraiser, this classic March ultra promises tough trails, great camaraderie and fin..
Challenge yourself on scenic trails at Up on the Downs on 1 March 2026, starting and finishing at Breamore House near Salisbury. Choose from a half marathon, 10k or 5k with a Canicross option and earn a finisher medal.
Tackle undulating trails, muddy paths and a shallow stream crossing on an adventurous six mile route at Baggeridge Country Park. Join the Action Heart Tuff Un on 1 March 2026 to test yourself and support a West Midlands cardiac charity.
Wight Riot is a mixed terrain coastal run at Hordle Cliff West, with sweeping views of the Isle of Wight and a scenic stretch past Sturt Pond Nature Reserve. Choose distances from 5K to ultra marathon and earn a medal for completing a lap o..