Trail Running calendar near Chepstow 2025-2026

We have found 311 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

BigSky Trails concludes the Classic Element Trail Series, sending runners from Hyde Common across open plains and winding New Forest trails with wide horizon views. Choose 18 mile or marathon and take a bespoke medal or opt for a tree.

Challenge yourself on the Chiltern 50 from Henley Showground, a scenic looped trail through rolling Chiltern countryside with options for walkers, joggers and runners. Enjoy camping, meals and support as you aim for a finishers medal.

Run through ancient woodland in the Forest of Dean at the Autumn Half Marathon starting and finishing at Speech House. This scenic 13 mile trail on well marked tracks supports local charities and awards a medal to every finisher.

Race scenic trails at Margam Country Park with castle views on a 5K or 10K loop. Fully marked and marshalled with chip timing, water stations and a finisher medal, ideal for new and experienced runners.

October 2026

Wild Run Cotswolds invites trail lovers to Cornbury Park for scenic, undulating single loop routes from 10K to the marathon plus a six hour 360 challenge. Family friendly, fully marked and marshalled, entries limited to 600 runners.

The The Maverick Jurassic Coast X-Trail will take place in Corfe Castle on Saturday 17 October 2026. This trail is organized by Maverick Race. You can run between 13 and 56 kilometers.

November 2026

Take on Dawn To Dusk. Day Light Robbery, a 12 hour loop challenge at Bridgend Miniature Railway where runners rack up laps on mixed trails, hills and technical descents. On site support, snacks and a bespoke medal await.

The Medal Mix Challenge Day 1, organized by Running Events Devon, takes place near Capel Lane, Littleham, Exmouth on November 28, 2026. This 7-hour timed event features a scenic 5.3 km out-and-back course on an old disused train line, fully..

The Medal Mix Challenge Day 2, organized by Running Events Devon, takes place on Sunday, 29th November 2026 near Capel Lane, Littleham, Exmouth. This 7-hour timed event welcomes runners and walkers of all abilities to complete as many 5.3 k..

December 2026

Take on the Nightmare Before Xmas Trail half marathon in Bridgend for a festive, muddy adventure across forest, road and rugged trail. Fancy dress is encouraged with a prize and finishers enjoy mince pies, hot drinks and a bespoke medal.

July 2027

The Birmingham Black Country Half Marathon is a running event held in the Black Country region near Birmingham. Organized by StuWeb Events Ltd., the race covers the half marathon distance of 13.1 miles. While specific details about the cour..