Trail Running calendar near Chepstow 2025-2026

We have found 294 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

The Breidden Hills Race, organized by Mercia Fell Runners, is a challenging fell running event set in the picturesque West Midlands. Participants will tackle a distance of 11.5 km with a total ascent of 790 meters, making it suitable for experienced runners. The race requires pre-registration and ha..

The Maverick Jurassic Coast 2025 is an exciting trail running event set in the stunning Isle of Purbeck, featuring four different routes: Ultra (101 km), Long (54 km), Middle (24 km), and Short (12 km). Participants will experience breathtaking views along the iconic Jurassic Coast, including famous..

The Centurion Autumn 100 is a challenging 100-mile continuous trail race set in the picturesque villages of Goring and Streatley along the River Thames. The course features a unique cross-shaped route consisting of four 25-mile out-and-back sections that utilize the Ridgeway and Thames Path National..

The Thames Trail Ultra is a challenging 47-mile point-to-point ultra marathon that takes place along the scenic Thames River, starting from Iffley in Oxfordshire and finishing in Henley-on-Thames. This popular event, previously known as the Thames Trot, features a diverse course that includes tarmac..

The Giddy Horse Backyard event is a unique running experience taking place at Piercefield Park, Chepstow Racecourse, on October 25, 2025. Participants can choose from 8-hour, 12-hour, 24-hour, and relay races, all set on a scenic 4.167-mile loop featuring a mix of woodland, parkland, and tarmac trai..

The Giddy Horse Half Marathon, Trail, & Steeplechase Obstacle Course Races is an exciting running event taking place on October 26, 2025, at Chepstow Racecourse in the UK. Participants can choose from various race options, including a half marathon, 8-mile and 4-mile trail races, and steeplechase ob..

The Black Beacon Mountain Trail Races are long-distance running events set in the stunning landscapes of the Bannau Brycheiniog (Brecon Beacons) and Black Mountains. Participants can choose from four race distances: 100 miles, 50 miles, 50k, and 21 miles, all culminating in Pontneddfechen. The races..

November 2025

The November Nightmare is an exciting running event taking place over eight days in Telford, Shropshire, celebrating its 10th year. Participants can choose from various distances each day, including 8 miles, a half marathon (approximately 16 miles), or a full marathon. Runners can enter for a single..

The Haldon Halloween Twilight Run is set to take place on November 1, 2025, in Haldon Forest, Exeter. Participants can choose from three distances: a 2.5 km fun run, a 5 km, or a 10 km run, including Canicross options. The event features no cut-off time, free race photography, and all finishers will..

The Dorset Hillfort Ultra is a scenic 38-mile running event set in the picturesque West Dorset countryside. Participants will traverse from one ancient hillfort to another, facing approximately 1,300 meters of ascent along the way. The route features a mix of flat sections and challenging climbs, of..

Endurancelife Gower offers a range of trail running events, including a 10K, half marathon, marathon, and ultra marathon, all set in the stunning natural beauty of Gower, the UK's first Area of Outstanding Natural Beauty. Participants can enjoy breathtaking views of cliff tops, woodlands, sand dunes..

UTMB Index

The Salt Settlers Six Hour Race is an exciting running event held in the picturesque Lower Otter Valley, designed for both runners and walkers. Participants aim to complete as many 4.4 km loops as possible within six hours, with options for solo or pairs relay teams. The course features a flat terra..

The Beacons Ultra is a thrilling running event featuring three race distances: a 49-mile ultra, a 26-mile marathon, and a 13-mile half marathon. Set in the picturesque town of Talybont-On-Usk, nestled in the Brecon Beacons, the event showcases a mix of trails, mountains, canals, and roads. Participa..

The One by the Canal is a scenic trail running event that takes participants on a beautiful journey along the Grand Union Canal, starting in Cowley and finishing in Watford. This half marathon offers runners a chance to enjoy the natural surroundings while challenging themselves on an intricate cour..

The New Forest Central Trail Run is a scenic trail running event held in the picturesque New Forest National Park, renowned for its natural beauty. Starting from Roundhill Campsite, participants can choose from three distances: 22km, 17km, and 10km, all featuring well-maintained gravel paths that me..

Dusk Till Dawn The Winter Edition is an exciting running event organized by Mad Running Junkies, set in the scenic Bridgend area of South Wales. Participants will tackle three 10-mile routes over a 12-hour period, starting at dusk and finishing at dawn. This unique challenge, a longer and more thril..

The Margam Trail Races, scheduled for November 15, 2025, invite participants to explore the scenic trails of Margam Park during the autumn season. The event features three race distances: a half marathon (21.1km), a 10km race, and a 5km fun run, each designed to challenge runners of all levels. The ..

The Bath Skyline event features a fun and challenging 10km off-road running series set against the stunning backdrop of Bath's iconic skyline. Participants can choose between day and night races, with routes that include a mix of solid stone paths, woodland trails, and open meadows, offering breatht..

The Broadway Marathon & Half will take place in Broadway on Sunday 16 November 2025. You can run 26 miles.

UTMB Index

The Rugged Radnage 10K Run is a challenging mixed terrain race set in the picturesque Chiltern Hills near Radnage. Participants will navigate a course that includes roads, trails, and footpaths, featuring both ascents and descents. The event also offers a 5K option, which covers half of the 10K rout..