Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 139 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
June 2027
An untimed inflatable obstacle course in Cardiff on 26 June 2027 offering 2.5k to 15k lap distances, inflatables, music zones, hydration and a finisher medal.
July 2027
Forest Warrior RISE AGAIN at Huntley Estate is a chip timed 8 to 10k obstacle mud run featuring climbs, crawls, hills and muddy swamps.
Flat races along former railway and riverside paths through the Wye Valley, featuring long tunnel sections, multiple feed stations and a choice of fun runs, 10km, half and marathon.
A 100 mile route across the Brecon Beacons on 24 July 2027 with 6143m ascent, 10 checkpoints, compulsory map and compass navigation and live GPS tracking.
An urban navigation challenge in Cardiff where participants are blindfolded, dropped at an undisclosed location and must return across 6, 10 or 15 miles without maps or GPS.
A 100 km race across the Brecon Beacons with 3178 m ascent, six checkpoints and a 24 hour limit; map and compass navigation plus prior ultramarathon experience are required.
Timed multi-lap event on a 3.28 mile out and back along Stroud Waterways offering distances from 5 km to ultra with a seven hour limit and a bespoke finishers medal.
Coastal ultramarathons along the Wales Coast Path with 100-mile, 50-mile and 50 km options, marked routes, GPS support and staffed checkpoints.
August 2027
A 57 mile point to point ultramarathon along the Thames Path from Kemble to Oxford with four checkpoints, mandatory kit requirements and a minimum average pace of 4.0 miles per hour. All finishers receive a bespoke medal and an MTC head visor.
Four day 186 mile Thames Path ultra made of four daily stages, with shared accommodation, kit transfer, mandatory kit checks and bespoke finisher medals.
Obstacle course event at Badminton Estate on August 15 2027 featuring Sprint 5 km, Super 10K, Beast 21K, a kids race and spectator access.
September 2027
Run through Westonbirt Arboretum's tree collections on courses from 1 mile to half marathon, with family activities on site.
An annual non-commercial 27.4 km fell race in the Black Mountains with five checkpoints, full kit required and online entry via Fabian4.
February 2028
A point to point 30 mile ultra along the Severn Path from Travelodge Stonehouse to Severn Beach. The course is mostly flat with two checkpoints, mandatory kit requirements, non refundable entry and finishers receive a bespoke medal and MTC head visor..