Trail Running calendar near Chepstow 2025-2026
We have found 333 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.
We have found 333 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.
Take on the scenic 16 mile Combe Gibbet to Overton race through Berkshire and Hampshire countryside on 29 March 2026. Limited to 250 runners, the event includes coach transfer to the start and kit transport back to the Overton finish.
Join the Run Upcote Spring Trail on 29 March 2026 at Upcote Farm for a scenic 5 mile off road race across bridleways, farm tracks and forest paths with testing climbs and descents. Entries are limited so expect a friendly, well supported ev..
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.
Inaugural BOWUM on 4 April 2026 from Monmouth: a 30 mile circular ultra across the Borderlands of Wales. Mostly trail, with scenic castle views on parts of the Three Castles Walk and Offa's Dyke Path, three manned checkpoints and a finisher..
Run the iconic Pendine Sands on 5 April 2026 with beach out and back routes from 5k to a 32.8 mile ultra. Expect a scenic tidal course with bespoke finisher medals and trophies for top runners.
Take on the Mortimer 10km through scenic Berkshire woodlands on Monday 6 April 2026. This undulating two lap off road course features chip timing, medals and a dog friendly canicross start for runners with dogs.
Take on West Wight 3 Hills, an undulating 8 mile coastal loop from Freshwater that climbs Tennyson Down and Alum Bay. Organised by Ryde Harriers, it is scenic, testing and gives every finisher a souvenir.
Take on the Henley River Half Marathon, 10K or Junior Race in Henley on Thames on 11 April 2026, with options for all ages including a kids race. Enjoy mixed terrain, riverside views, medals, free photos and a buzzing event village.
Enjoy stunning coastal, woodland and dune trails at Oxwich Bay with 5 km, 10 km or a self navigated half marathon. Part of the Run The Trails Series, the event is timed and all finishers receive a medal.
The Big Cheese is an off road fell race in Cheddar, Somerset, covering 15 miles across the Mendip Hills with over 2,000 ft of climb. Take on a fully marked course and enjoy a finisher's medal plus tea and cake at the end.
Take on the Wild Horse 200 series: two epic 200 mile trail ultramarathons across Welsh trails and mountains. Run the South Wales coast route from Chepstow to Worm's Head in April or the Mid Wales loop from and to Machyntlleth in June.
Take on the inaugural MTC Gelert 47 mile ultra from Barmouth to Llanidloes on 16 April 2026, the third day of the MTC CYMRUN end to end. Limited field, bespoke medal for all finishers and real time tracking for supporters.