Trail Running calendar near Chepstow 2026-2027

We have found 464 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

A trail-focused marathon and half marathon around Broadway in the northern Cotswolds on 15 November 2026. Routes feature mainly unpaved track and trails, climbs to Broadway Tower, village and escarpment scenery.

Night trail running from Corfe Castle on 20 November 2026 with three waymarked routes across muddy tracks, ridges and woodland. The long route includes one outpost, toilets are only at the venue, and dogs are not permitted.

The Smurf Run at Dare Valley Country Park is a seven hour Time Challenge on well maintained park paths, with distances from 3 km up to 50 km. Finishers receive themed medals, distance pins and a goody bag with vegan options.

Night time looped trail run at Moors Valley Country Park on 21 November 2026 with 10 km, 20 km or 30 km options, compulsory headtorch and free main car park; runners can choose a tree planting option instead of a medal.

A scenic, off-road 10-mile trail race in the New Forest on 22 November 2026, organised by Totton Running Club. Entry includes medal, medical cover, parking, goody bag and age-category trophies; the route is mainly trail and undulating.

An off road hill race around Brent Knoll in Somerset on 22 November 2026, roughly 6 miles with a steep summit climb and muddy trails. Facilities at the BASC sportsground include parking, toilets, refreshments and a limited bag drop.

A night time off-road 10 km race at The Wyre Forest with compulsory torches, canicross allowed, medals for all finishers and prizes for the top three men and women. Early reduced fee for the first 20 entries.

An 8 hour timed road event near Exmouth on a tarmac route along an old disused train line. Laps are 5.3 km and entrants are limited to 75; medals come from a mixed stock and specific requests can be made to the organiser.

A short fell race of 5.7 km with 485 m of climb on Blorenge near Llanfoist, Abergavenny. Mostly unmarked up-and-down route with steep technical terrain; basic navigation and full kit are recommended.

Two trail distances on 28 November 2026 around Machen, featuring wooded single track, ridgeway exposure and steep climbs. The half course is fully marked while the marathon requires self navigation with marshals at key points.

An eight hour timed event near Littleham, Exmouth on 29 November 2026. Participants run or walk laps of 5.3 km on a measured tarmac out and back route and finishers receive a medal mix.

The final race of the 2026 RTT Series takes place in Afan Forest with separate 5 km and 10 km routes from Bryn Bettws Lodge. The event features chip timing, finisher medals, marked and marshalled routes and water stations.

Trail races at Mapledurham Estate offering 10K, 10 Mile and Half Marathon routes over muddy paths and woodland, with on-course water, finish refreshments and race amenities included.

A trail running event on 29 November 2026 at Charborough Estate through dense Bere Wood, with 10 km, 21 km and a two person relay across technical, marked trails. Facilities include one aid station, toilets and medical support.

A fell time trial from Little Stretton to the Stiperstones that requires navigational skills and benefits from local knowledge. Entry is on the day with fees of £8 for adults and £2 for juniors under 17.

A club organised race at Blaenwern Holiday Centre in Llanybydder on 29 November 2026 covering 6.5 miles on mixed surfaces; junior and senior categories are included and past results are archived online.

A lap based road event at Rhydycar, Merthyr Tydfil, on a 5.3 km AUKCM certified tarmac circuit along the Taff Trail. Runners choose how many laps to complete within a seven hour limit and can opt for a no medal entry.

A 23 mile clockwise tour around Worcester and Droitwich starting at Gheluvelt Park, mostly on traffic-free paths. Solo and two-person relay options are available, with three on-route control points and a six-hour completion limit.

December 2026

Two coastal routes start from Hengistbury Head in Bournemouth, offering a flat, traffic-free 10 Mile or 10k run along seafront paths with chip timing, water stations and a finisher's medal.

Trail races of 10K, half marathon, marathon and ultra run from Swanage along the Jurassic Coast Path on 5 Dec 2026, with mixed trail and grass terrain and significant ascent. The event counts toward the Endurancelife 26-27 season leaderboar..

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