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 40 mile towpath event from Malpas to Brecon on 24 April 2027 with three aid stations, volunteer Canal Crew support and a 15 hour cutoff.
May 2027
A 5 km obstacle event at Coopers Field Bute Park Cardiff with mixed tarmac and grass underfoot, staggered wave starts, on course marshals and fundraising support.
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.
Race for Life at Coopers Field, Bute Park offers 10k, 5k and 3k routes on mixed grass and tarmac while raising funds for Cancer Research UK.
Two Welsh trail ultras based in Abergavenny, offering 100 mile and 100 km routes on Offa’s Dyke, the Cambrian Way and the Beacons Way with on-course support.
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.
Four marked trail races around Minchinhampton and the Cotswold Edge on 9 May 2027, from 12.2 km to 64.5 km, with checkpoints, required 500 ml water container and finishers medals.
Two route options, 26.5 miles and 16 miles, start from Trehafod Community Village Hall across the Rhondda Valleys with checkpoints, refreshments and a hot meal at the end.
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.
Backyard format at Eastnor Castle Deer Park with a solo 8 hour 33.3 mile event on a 4.167 mile loop and continuous 8 hour relay options for pairs and teams.
Mud-focused trail run at Eastnor Castle offering 3km, 6km and 10km routes with natural obstacles, muddy troughs, on-site camping and basic facilities.
An inflatable obstacle fun run at North Somerset Showground on 22 May 2027 offering lap based distances from 2.5 km to 15 km with giant slides, tunnels and music zones.
Altered Backyard Ultra at Tockington Manor on 29 May 2027 with a 4.167 mile loop each hour, capped at 30 loops and a fastest lap finish if runners remain.
June 2027
Three urban orienteering races across Bristol and Bath, 4–6 June 2027, with single entry options and weekend SI card hire.
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.