Trail Running calendar near Chepstow 2026-2027

We have found 354 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

Experience the beauty of the South Downs National Park on a point to point trail run from Arundel to Winchester featuring ultramarathon or marathon distances with fully marked courses and stocked aid stations.

An 11K multi terrain run around Bratton on 21 March 2026 with panoramic views, prizes across age categories and medals for finishers. Places are limited to 200 and entries close 14 March 2026 or earlier.

This scenic trail half marathon winds through the heart of the Forest of Dean. It doubles as the British Trail Running Championships short distance event, offering a chance at a national title. The well marked course starts and finishes at..

Take on the Red Warrior multi terrain races at Margam Country Park on 22 March 2026, with 5K, 10K and 20K routes for solo runners and canicross teams. Expect varied trails, friendly vibes and a great day out for competitors and their dogs a..

Cross Dartmoor from east to west on this 50km or 16 mile traverse featuring self navigation and live GPS tracking. Runners can participate solo or in teams and enjoy fully supported feed stations and a finish line medal.

Experience a unique urban trail adventure starting in the heart of Bristol. Choose between 25km and 55km routes featuring riverside paths, woodland trails, and iconic views of the Clifton Suspension Bridge.

The Bath 50 Ultra Challenge offers a scenic looped route around the historic city on 28 March 2026. Choose from 50 km, 29 km, or 10 km distances, with full support including rest stops and meals. It's open to walkers, joggers, and runners,..

UTMB Index

The Exeter Trail Races offer a 10K and Half Marathon on the scenic, off-road trails of Escot Park. Both distances feature canicross options for runners with dogs. Expect climbs, potential mud, and a finisher's medal at this established even..

Run as many laps as you choose on this forest trail course in Hurn Forest. Enjoy a well maintained loop with distances ranging from 5K to ultra marathon and support forest conservation with your entry.

The Ultra in the Black Country returns for its ninth year in March 2026. This 32-mile scenic loop starts and finishes at Baggeridge Country Park. The traffic-free route explores disused railways, canal paths, and tunnels, and can be run sol..

Tackle the hills and mud of Axminster in the Minster Challenge. Choose from a challenging 12 km, a 5 km route, or a family-friendly 3 km fun run. All finishers earn a medal, and the event features a supportive trail running atmosphere.

Experience a scenic 16 mile multi terrain race through the Berkshire and Hampshire countryside. This undulating cross country course offers bus transport to the start and kit transfers for all participants.

Join this multi terrain challenge through private estates in the rolling hills of mid Devon. Choose between a ten mile trail race with over 600 meters of ascent or a five kilometer fun run and walk.

A five mile off road trail at Upcote Farm on 29 March 2026, limited to about 300 places. The route features farm roads, bridleways and forest tracks, with chip timing, medals for all and prize categories for juniors and veterans.

Take on the finale of the Shropshire Winter Series at Ercall Wood, a tough 8.8 km fell race climbing 519 m on scenic Ercall Hill. Pre entry or on the day entries accepted and junior races run for ages 12 to 17.

Experience a premier multisport challenge at the Culden Faw Estate featuring road and offroad duathlons plus a six hour endurance race for all bike types.

Family friendly event at Telford Town Park with 2.5K and 5K routes, a finisher teddy for each participant, and a post-race teddy bears picnic. The event raises funds for Birmingham Children's Hospital and encourages fundraising.

Join the 45th Wrekin Fell Race in Telford for a classic Category A short fell race featuring 1700 feet of climbing. Finish the Shropshire Winter Series at Ercall Wood Academy with distances for both senior and junior runners.

April 2026

Testway Ultra on 04/04/2026 invites runners to tackle scenic 40 or 50 mile routes along Hampshire's Testway from Linkenholt to Totton. Well marked trails, regular aid stations and a shuttle make for a friendly, memorable ultra.

The BOWUM is a 30-mile ultramarathon exploring the historic Welsh borderlands. The circular route from Monmouth passes three ancient castles and features a mix of trail and road. This inaugural event offers supported checkpoints and encoura..