Trail Running calendar near Chepstow 2025-2026

We have found 325 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

Join the Spooky Sprint at Pengethley Manor, Ross on Wye on 24 October 2026 for a tough offroad Halloween race through two vineyards. Choose on course or virtual options from 5k up to ultra and enjoy a scenic, challenging looped course.

Join the Zombie Shuffle at Pengethley Manor on 25 October 2026 for offroad laps through vineyards and rolling hills, with distances from 5k to ultra to suit walkers and runners. Finisher medals and virtual entry options make it easy to join..

Take on the Black Beacon Mountain Races, a series of mountain trail challenges across the Brecon Beacons and Black Mountains from Hay on Wye. Choose from long distance courses with GPS routes, rugged ridgelines and full mountain support.

November 2026

Tackle 35.9 miles across Dorset hillforts with 1,300 m of ascent on mostly off road trails that can be muddy or hard packed. Scenic views, well stocked stations and a true trail test await.

Take on the Apocalypse Run, a thrilling 10 mile off road trail through the Cotswolds near Stroud with muddy, undulating terrain and a finisher medal. Canicross runners welcome and entrants should be able to complete the course within 2 hour..

Tackle the North Coast 110 Exmoor Coast Ultra along the stunning South West Coast Path, finishing in Minehead. Choose distances from 38 km to 110 miles across dramatic Exmoor terrain with self navigation and GPS tracking.

Explore Gower's wild coast on 7 November 2026 with 10K, half marathon, marathon and ultra trail options across cliffs, dunes, woodland and beaches. Expect tough terrain, stunning views and a friendly post race gathering.

Run under the stars through the rolling Chiltern Hills at Stonor Park in November with three waymarked trail options from 7 to 17 km. Expect a fully marked, timed night race; bring a headtorch and enjoy a finishers medal and event atmospher..

Run the Maverick Oxfordshire Trail at historic Stonor Park in the Chilterns AONB with 7 km, 13 km or 22 km routes through deer filled woods and under soaring red kites. Expect steep climbs, wild views and fully marked, timed trails.

Run scenic tracks through ancient New Forest woodland near Brockenhurst, with routes up to 21.6 km and regular sightings of ponies and deer. Chip timing, aid stations and a finisher medal make this a friendly autumn trail event.

Run under the stars around historic Corfe Castle on muddy, single track trails with views over Poole Harbour and chances to spot Sika deer. Choose 5, 11 or 15 km routes and finish with a metal medal and post race food.

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

Run along Bournemouth seafront at Hengistbury Head with sea views and a memorable stretch past Boscombe Pier. Choose 10 mile or 10 km traffic free routes that are largely flat, with chip timing, a medal and post race refreshments.

Take on the Cardington Cracker, a 9 mile fell race near Church Stretton with 793 m of climb and breathtaking Border views. Pre entry only and limited parking mean early sign up is essential for this rugged, rewarding test.

Join the Nightmare Before Xmas Trail half marathon on 19 December for a festive, scenic and challenging trail through woodland, steep climbs and muddy sections. With small fields, fancy dress prizes and mince pies, it is a festive challenge..

January 2027

Kick off 2027 with a 7 hour timed challenge in Exmouth on the scenic tarmac of the old Capel Lane rail line. Tackle as many 5.3 km laps as you can on this mainly flat out and back course and earn a finisher 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..