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.
January 2027
Timed multi-lap run on a 2.62 mile canal out and back in Brimscombe with distances from 5 km to ultra and a seven hour limit; medals for all participants.
About 9 miles of steep, multi‑terrain running in the Slaughterford valley with roughly 900 feet of climb. Winter race scheduled for 24 January 2027.
A winter fell race near Abertillery: 9 km with 550 m climb, mandatory kit, flagged mandatory loop and navigational skills required.
Trail races at Oldbury Court Estate near Bristol offering 4 Mile, 10km and half marathon routes through woodland and riverside paths with live chip timing and finisher medals.
February 2027
Night running at Westonbirt Arboretum among over 2,500 tree species, with 5 km and 10 km options on solid trail-like surfaces.
A Backyard Ultra near Crickhowell on 6 February 2027 featuring repeated 4.2 mile loops, a reversed final race lap, trophies for final lap winners and medals from 32 miles.
Timed multi-lap run in Parc Taf Bargoed with 5.3 km laps and distances from 5 km to ultra, offering bespoke medals or a lower cost no medal entry.
5 km and 10 km trail style races at Westonbirt Arboretum on 7 February 2027, through areas with over 2,500 tree species; tickets sold out.
Doynton Hard Half Marathon on 7 February 2027 is a hilly, muddy half marathon with a 3.5 hour cut off and race kit including a t shirt and goody bag.
Mountain to city winter races from Brecon to Cardiff featuring a 75 km ultra and a 26.2 mile marathon on unmarked mountain routes with GPS navigation required.
A one way, fully marked 70k ultramarathon along the Taff Trail from Brecon to Nantgarw. The route moves from mountain landscapes to former industrial valleys and includes coach transfer to the start, checkpoints and live GPS tracking.
A chip timed 5 km, 10 km and half marathon at Ashton Court, Bristol supporting Shelter on a mixed trail and path course with lap based routes.
A timed event on a 2.62 mile out and back canal route with flexible rock up and run starts. Distances range from 5 km through marathon and beyond, with a seven hour time limit and a finisher medal for all.
A multi-distance running event in Bath featuring two converted railway tunnels and a start and finish at Brickfields Park, with funds raised for Sustrans.
A 12 mile cross country race in Dursley on 21 February 2027 with over 2000 feet of climbing across woodland trails, mud, roads and steep climbs.
An approximately 8-mile multi terrain race around Sorbrook and Sluvad near Cwmbran with marshalled routes, medical cover, goody bags and age-category prizes.