Trail Running calendar near Chepstow 2026-2027

We have found 411 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

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.

Looped trail event from Bath Racecourse with **50 km**, **29 km** and **10 km** options, covered rest stops, medical and massage teams, GPS tracked routes and finishers' medal and T shirt.

UTMB Index

Trail races at Escot Park return for a third year, offering a half marathon and an approximately 10.5 km 10K with canicross options. Off road routes include climbs and muddy sections, with chip timing, medals and category prizes.

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..

A trail event in Axminster on 29 March 2026 with 12 km, 5 km and 3 km routes over hilly, muddy terrain. Medals, basic facilities and limited parking at the school are provided.

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.

Celebrate a birthday with a Cakeathon in South Wales. Run or walk a flexible number of laps on a 5.3km course through Parc Taf Bargoed. Choose your distance and enjoy a 7-hour event with a finisher's medal and cake.

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

A trail ultra in Hampshire on 4 April 2026 with 50 mile and 40 mile route options along the Testway. Aid stations every 10 miles, marshals and an on course medical team provide support and an optional shuttle returns runners to the start.

A 30 mile circular ultra on 4 April 2026 around Monmouth, covering parts of the Three Castles Walk and Offa's Dyke Path with 4,258 ft of elevation and two fully stocked checkpoints.

Test your endurance with this 12 hour Backyard Ultra format race featuring a 4.167 mile loop through the Purbecks. Run as an individual or in a team while enjoying the scenic Jurassic Coast and a lively event village.

Experience the unique challenge of racing on the firm sands of Pendine Beach. Choose from five distances ranging from 5k to an ultra marathon on a course famous for land speed records.

Enjoy a festive multi terrain run around the picturesque Chasewater Reservoir with distances ranging from a Junior Run to 20 km. This undulating course features professional timing, bespoke medals, and a friendly atmosphere.