Trail Running calendar near Chepstow 2026-2027

We have found 357 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

Choose your distance from 3 km to ultra marathon and tackle a 7 hour time challenge around scenic Dare Valley Country Park. Enjoy lap aid stations, vegan snacks and a finisher medal for anyone completing at least 3 km.

A family oriented 2.5K and 5K event at Aston Park where every finisher receives a cuddly teddy. The run raises funds for Birmingham Children's Hospital and finishes with a teddy bears picnic.

May 2026

A weekend trail running festival based at Offwell Village Hall with multiple ultra and shorter courses, live GPS tracking and aid stations. Events run over the first bank holiday weekend in May and include camping and bag drop services.

An out and back ultramarathon from Abberley Village Hall following the Worcestershire Way with GPX navigation. Races of 23, 31, 38 and 47 miles are offered; the full route has about 2,941 m of ascent.

Three circular trail races from Brecon through the Bannau Brycheiniog National Park, offered as 100 km, 75 km and marathon distances with marked routes, checkpoints, GPS files and mandatory kit for mountain navigation.

UTMB Index

A circular 30 mile ultra through mid Wales on 2 May 2026, starting and finishing at Dol Lys Camp Ground in Llanidloes. The route follows Sarn, Glyndwr’s Way, Severn Way and Wye Valley Walk and reaches the source of the River Severn.

A trail event on 2 May 2026 at Carding Mill Valley offering a half marathon (one 13.1-mile lap) or a full marathon (two laps). Entries for the main race are limited to 200 and a virtual option runs the week of May 4th.

Run Silchester offers scenic trail races from the village playing field along the Roman Wall and through ancient woodland, with a 2.5 mile fun run plus 5 and 7 mile trail races. Enjoy festival vibes, medals and community fundraising for the..

Coastal and moorland trail runs from Caffyns Farm, Lynton, with five distances from 5 km to 56 km, outposts and GPS tracks on the Ultra, plus reusable cup policy and conservation support.

UTMB Index

A five mile off road race around Hurstbourne Tarrant on Saturday 2 May following part of the Test Way through woods and farmland. The volunteer organised event donates proceeds to local charities and offers timed entry fees by date and affi..

Explore the Cotswolds trails at the Tempo Trail Races. Choose from five distances including a new 50K ultra option. The event starts and finishes at the Ilmington Sports & Social Club.

The 2026 Rapid Relays offers solo and team trail relays, alongside a Sunrise Run and a downhill time trial. Set on the woodland trails of the Culden Faw Estate, the event features chip timing and a dedicated race village. Camping is availab..

A spring trail running event through bluebell woodland near Manswood, Wimborne offering Half Marathon, 10K and 5K courses. Way marked routes feature aid stations, chip timing, finishers medals, trophies, an event photographer and a medic te..

The Phoenix Running - Brimscombe will take place in Brimscombe on Sunday 3 May 2026. You can run between 5 and 42 kilometers.

The Marlborough Downs Challenge offers two off road trail races across the North Wessex Downs, a 33 mile ultramarathon and a 20 mile trail. Routes visit Wansdyke, Avebury and other Wiltshire landmarks with notable elevation.

Trail running festival around Winchester offering 14 mile, 19 mile, marathon and 50K ultramarathon routes on marked, marshalled trails with aid stations, bag drop and an option to plant a tree instead of a medal.

An annual off road race at Hood Memorial Hall in Devauden on trails through Chepstow Park Woods, offering 10k, 5k, a 2.4k for ages eight and over, and a 60m junior dash with proceeds supporting local search and rescue.

A provisional cross-country race at Sheinton Church near Cressage on 6 May 2026. The course is 5.3 km with 100 m ascent, entry is on day only with a fee of £8, and 2026 will be the last running.

Enjoy scenic off road racing through Collingbourne woods with a chip timed half marathon or 10 km at Crawlboys Farm in Ludgershall on 9 May 2026. Marked trails, aid stations, medals and lively support make this a must for trail fans.

A coastal and countryside route following the Sid Valley Ring walking trail, with an uphill start, coastal views across Lyme Bay and a new 13.5 km Third Marathon joining the half route. The event is open to runners and walkers.