Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 135 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A four-day, 184-mile Thames Path ultra from the river source to the Thames Barrier with daily stages, included accommodation for days one to three, bespoke finisher medals and compulsory mandatory kit and minimum pace requirements.
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.
A pancake-flat 10 km out and back along the Brecon and Monmouthshire canal between Gilwern and Llangattock, set in the Brecon Beacons National Park. Finishers receive a medal, there is a drink station at 5 km, and entries are online only.
A social 5K in Newport with music and mobile speakers, meeting and finishing at banc coffee & records; tickets are free and under 14s require a parent or guardian.
Obstacle course races at Badminton Estate on 16 August 2026, with Sprint 5 km, Super 10 km, Beast 21 km plus a kids race and spectator options.
A timed, flexible run along a 3.28 mile out and back route beside the Stroud Waterways canal. Runners choose distances from 5 km up to ultra and may complete as many laps as they wish within a seven hour limit.
Join the Crook Peak Cake Race in Axbridge on Wed 19 Aug 2026 for a spirited 3 mile fell challenge across stunning Somerset hills, finishing with cake and community cheer. On the day entry available for runners aged 14 and up.
A 9.8 km traverse near Pontypool with a 291 m climb, junior race distances and three-person team entries.
September 2026
A new 15 mile trail event in September 2026 on the Rhymney Valley Ridgeway Walk, with 2,267 ft of ascent, mostly off-road terrain, one fully stocked checkpoint and organised entry support from Rudry to Parc Penalta.
Trail-style races through Westonbirt Arboretum offering Half Marathon, 10 km, 5 km and a 1 Mile fun run across September and February events.
A riverside running festival on 6 September 2026 with 10 km, 5 km and a family fun run. Chip timing on multi terrain routes, canicross options, basic on site facilities and medals for all finishers.
A small community trail race in Epney, Gloucestershire covering approximately 10 miles along canal towpath and local footpaths, starting and finishing near The Anchor Inn.
Run as far as you like at Alice in Runderland, a timed multi lap event at Parc Taf Bargoed with flexible start times and on course support. Choose from one lap up to marathon and earn a bespoke finisher medal.
A long, non-commercial fell race in the Black Mountains with a 27.4 km route and 1586 m of ascent. The event uses five checkpoints, requires full navigational kit, and operates on open access land with no on-course water provided.