Trail Running calendar near Chepstow 2025-2026
We have found 311 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.
We have found 311 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.
Test your endurance at the Elephant Challenge in Salcey Forest on 24 March 2026, a timed 6 hour event where you run as many 3.5 mile off road laps as you like. Enjoy scenic forest trails, an optional medal or tree token and a chance to supp..
The Way of the Dead is a challenging 50k running event traversing Dartmoor from east to west, organized by Wild Running. Participants can compete solo or in pairs, with live GPS tracking and three checkpoints that also serve as feed station..
Tackle 16 miles of undulating trails from Combe Gibbet to Overton across scenic Berkshire and Hampshire countryside. Managed transfers and kit transport included make this a classic spring cross country adventure.
Run Upcote Spring Trail is a limited entry 5 mile off road route around Upcote Farm near Cheltenham, featuring forest tracks, climbs and scenic Cotswolds views. Expect chip timing, medals for all finishers and a friendly festival vibe.
Challenge a scenic 32 mile loop from Baggeridge Country Park, largely traffic free along canals and old railways. Enter solo, pairs or team of 4, face the 2.7 km Netherton Tunnel with a head torch and finish with a medal and a beer.
Inaugural BOWUM is a 30 mile circular trail in Monmouthshire linking Skenfrith, Grosmont and White Castle via the Three Castles Walk and Offas Dyke Path. Enjoy rolling hills, well stocked checkpoints and no time limit.
Take on the Mortimer 10km on Monday 6 April 2026 at Mortimer Fairground, a scenic off road route through local woodlands and bridleways. A dog friendly canicross 10 km option lets you enjoy the race with your canine companion.
Challenge yourself on an 8 mile undulating trail around Freshwater, climbing about 900 feet and passing iconic spots like Tennyson Down and Alum Bay. Limited to 175 entries on 6 April 2026, this rugged multi terrain route offers stunning co..