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
Races in Bath that run through two restored tunnels on a shared use path, with distances from 500m Colourburst to an ultra marathon.
A roughly 6 kilometre mixed-surface race through Blaise Castle Estate in Bristol, held annually in early June. The event has individual and team prizes, a minimum age of 16, and facilities based around the clubhouse.
A backyard ultra at Breakheart Quarry where runners repeat a 6706 metre loop every hour until one person remains; the event includes camping, marked trails and on course support in the Cotswold countryside.
Military themed D Day series run at Parc Taf Bargoed with 5.3 km laps; choose distances up to ultra within a seven hour time limit and earn commemorative medals.
Off road races around Cheddar Gorge and the Mendip Hills on 13 June 2027, from 1 km to marathon, plus an Omnium and UTMB Index Half and Marathon.
Timed run along a 3.28 mile out and back canal route in Stroud with flexible starts, multiple distance options and a seven hour time limit.
Pretty Muddy 5k at The Downs in Bristol is an obstacle course on mainly grassy terrain with a 28 m ascent, organised by Cancer Research UK to raise funds for research.
Race for Life at The Downs in Bristol offers 10k and 5k routes on mainly grassy loops, timed by chip and run to raise funds for cancer research.
Inflatable obstacle course and fun run at Heath Park Cardiff on Saturday 26 June 2027 with distance options from 2.5k to 15k and family entry rules.
July 2027
A mud run and obstacle race at Huntley Estate featuring climbs, crawls, muddy swamps and a chip timed 8 to 10 km course, with bespoke medal and event t-shirt for participants.
Flat races along the Wye Valley Greenway and through the lit Tidenham Tunnel, with events from 500 m Colourburst to a full marathon.
A 100 mile self-navigation ultramarathon across the Brecon Beacons with 6143 m ascent, 10 checkpoints, strict qualifying criteria and a 40 hour cut off.
A navigation challenge in Cardiff where participants are blindfolded, dropped at an undisclosed location, and must find their way back without maps or GPS.
A self-navigated 100 km across the Brecon Beacons with 3178 m ascent, six staffed checkpoints, strict qualifying criteria and a 24-hour cut-off.
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.