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.
April 2027
A last-person-standing Backyard Ultra at the Medieval Village, Cosmeston Lakes: runners repeat a fixed 6706 m loop each hour until one athlete completes one more loop than anyone else. Camping and on-site facilities are provided.
May 2027
A 5k obstacle course at Coopers Field, Bute Park, Cardiff, with tarmac paths and grassy sections that can get boggy after rain. The event raises funds for Cancer Research UK and uses staggered wave starts; participants must be 13 or older.
A hilly, technical Backyard Ultra at Blaise Castle Estate, Bristol, using hourly 4.167 mile laps; the 2027 event is sold out and the waiting list is closed.
A Welsh trail event with 100 mile and 100 km routes along Offa's Dyke Cambrian Way and Beacons Way, supported by aid stations and volunteer crews.
Timed event on a 3.28 mile out-and-back canal route in Stroud on 08 May 2027, with choice of distances from 5 km to ultra and a seven hour limit.
A trail marathon around Cardiff with about 1,300 m of climbing, mixed off-road terrain, partial self-navigation, checkpoints and support during the Radyr and Morganstown Festival.
Stroud Trails on 9 May 2027 offers four marked trail races across the Cotswolds with checkpoints, water stations, marshals and a mandatory 500 ml water carry.
Two waymarked routes from Trehafod Community Village Hall through the Rhondda Valleys with checkpoints, refreshments and a completion certificate.
A 10k trail run at Symonds Yat with riverside views and a notable final one kilometre climb. The mostly off road course includes long gravel firetracks and on site coffee and hot food.
An inflatable obstacle run at North Somerset Showground with 2.5 km laps, multiple distances, music zones, on-course water and a finisher's medal for every participant.
Altered Backyard Ultra at Tockington Manor on 29 May 2027, running hourly 4.126 mile loops up to a 30-loop cap for about 201 km, field capped at 250 runners.
June 2027
A varied running event in Bath that takes competitors through two long, lit railway tunnels and starts and finishes at Brickfields Park.
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.
An off-road race series around Cheddar Gorge and the Mendip Hills with distances from 1 km to marathon and an Omnium option; half and marathon hold UTMB index status.
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.
A Pretty Muddy 5k at The Downs in Bristol with grass start and finish, mixed terrain and obstacles to climb, crawl and slide. Staggered wave starts apply and the event supports Cancer Research UK with a minimum fundraising target.