Trail Running calendar near Chepstow 2026-2027

We have found 461 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

A Halloween series event at Pengethley Manor offering 5k, 10k, half, marathon and ultra distances on a tough offroad course with vineyard laps. Entrants have seven hours to finish and virtual participation is available.

Day one of a two day mountain marathon at Westermill Farm, Exford, featuring a 40 km course with 1800 m of climb. Teams of two must pre-enter and the entry fee covers both race days and campsite.

A hip hop themed coastal run at Milford on Sea offering flexible distances from 5K to ultra and 5.3 km laps, with aid stations, a cupless policy, bag drop and a themed medal.

The Zombie Shuffle at Pengethley Manor offers 5k, 10k, half marathon, marathon and ultra options on a tough offroad course with a seven hour time limit. Virtual entries are available worldwide with medal options for paid entrants.

Mendip Muddle is a 20 km multi terrain fell race in Somerset with about 420 m of climbing. Headquarters are at Charter House Outdoor Activity Centre; on course water and first aid are provided and prizes are awarded by category.

Routes along the Grand Western Canal in Tiverton include Marathon, Half Marathon and 10k options on hard packed gravel towpaths. The event is cupless so runners must carry their own water and finishers receive a bespoke medal.

A series of mountain trail races across the Black Mountains and Brecon Beacons offering four distances from 21 miles to 100 miles. Routes combine marked sections, GPS navigation and staffed checkpoints with mountain safety cover.

An evening trail event at Haldon Forest Park on 30 October 2026 offering a 2.5 km fun run plus 5 km and 10 km running and canicross options, free race photography and a Halloween 2025 medal for each finisher.

A 32 km, 1800 m ascent mountain event at Pen y Fan featuring three separate ascents via six different paths, with Classic and 16 kg weighted categories. Navigation is required and control marshals monitor checkpoints.

Winter Sugar Loaf is a 9.6 km fell race near Abergavenny on 31 October 2026 with 485 m of ascent; entry via Fabian4 costs £9. The route is partially marked, full WFRA kit is mandatory and limited parking is available.

A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.

November 2026

An off road ultramarathon from Maiden Newton of about 35.9 miles with roughly 1,300 m of ascent, passing hillforts and coastal views. Six aid stations offer water and cake, GPX files and maps are provided for navigation.

A 10 mile off road trail in Stonehouse near Stroud on 1 November 2026, starting with about one mile uphill followed by nine miles of undulating muddy trails. Canicross runners are welcome and there is a 2 hour 30 minute cutoff.

Eight-day race series in Telford offering 8 miles, 16 miles or a 26.2 mile marathon each day. Each day is a separate race with its own medal and Race HQ at The Unicorn Inn in Little Dawley.

A series of self-navigated coastal ultramarathons and a 38 km challenge along the South West Coast Path, featuring GPS tracking and ITRA/UTMB index points. Distances range from 38 km to 110 miles, with significant coastal climbing and varie..

Trail races at Oxwich Bay on 7 November 2026 with 10K, half, marathon and ultra routes across cliff tops, dunes and beaches. Part of the Endurancelife 2026-2027 season and included on the Season Leader Board.

Night trail running at Stonor Park in the Chiltern Hills on 7 November 2026 with three waymarked routes of 17 km, 13 km and 7 km. Outposts, parking, timed results and finish facilities are provided; dogs are not permitted.

A mixed terrain running event around the Brecon Beacons on 7 November 2026, held across trail, mountain, canal and road. Three distances are offered and conditions in mid-November can range from bright sunshine to freezing temperatures with..

A twilight off road 10k around Eastbury Park and Chettle with wooded sections and historic landmarks. Medals, trophies and refreshments included and entries are limited to 200.

Experience a 30 mile ultra marathon through the heart of the Brecon Beacons featuring the summit of Pen y Fan. This trail event offers technical terrain and scenic reservoir views with a strict 200 runner limit.

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