Trail Running calendar near Chepstow 2026-2027

We have found 479 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

A trail event at St Giles House offering races from junior fun runs to a marathon, virtual entries, camping and a dog option, while supporting the New Forest Marathon Community Fund.

A Bronze Ticket backyard ultra on Portland where competitors run a 6,706 m loop each hour until one runner remains. The route offers coastal views, quarries and mixed surfaces, with on-site camping, chip timing and medic cover.

A trail running weekend around East Devon from Offwell Village Hall, with four GPS-tracked routes through woodland, national landscapes and the Jurassic Coast, on-site camping, aid stations and finishers' kit and meal included.

May 2027

Out-and-back trail event from Abberley Village Hall with 23, 31, 38 and 47 mile options; the full route includes about 2,941 m ascent, GPX navigation is provided and checkpoints enforce a 13 hour maximum time.

A five mile off road race through woods and farmland around Hurstbourne Tarrant in the North Wessex Downs. Organised entirely by volunteers since 2009, the annual event donates all proceeds to local charities.

A 5k obstacle course at Coopers Field, Bute Park, Cardiff, with tarmac paths and grassy sections that can get boggy after rain. The event raises funds for Cancer Research UK and uses staggered wave starts; participants must be 13 or older.

A Pretty Muddy 5k obstacle course at Lydiard Park on 01 May 2027 featuring mixed paths, hills and muddy obstacles. The event has wave starts, blue badge parking on grass and a minimum fundraising target of £50.

An official Backyard Ultra at Blaise Castle Estate on 1 May 2027 where runners complete a 6.7056 km loop each hour until one runner remains. The woodland loop is hilly and technical, head torches are mandatory at night and minimum age is 20..

Trail routes from 5 km to 56 km traverse Exmoor coastline and inland valleys with steep climbs and technical terrain. The event offers marked courses, outposts and onsite camping, and a portion of entries supports CareMoor.

A one day Cotswolds trail event on 2 May 2027 offering six distances from 10K up to a 100KM ultra plus a two person 100KM relay, with feed stations, baggage support and trackers on the ultra routes.

A woodland trail relay at Culden Faw Estate near Henley on Thames offering solo, pair and team entries with camping available. The course uses estate tracks, features a climb before 3 km and is chip timed with live lap splits.

A spring trail event in Harewood Forest near Andover offering 5k, 10k, canicross and a childrens fun run on undulating, multi terrain courses with marked routes and on course marshals.

An off-road half marathon and 10 km trail event near Ludgershall through bridle and woodland tracks, with chip timing, stocked aid stations, full medical support, finishers' medals and prizes for the top three men and women.

Pretty Muddy 5k at Weston Park is an obstacle course across paths, tracks and grass with some hills and on site parking. Entrants must be at least 13 and take part in staggered wave starts while raising funds for Cancer Research UK.

Multiple trail race distances in the Stroud area using towpaths, disused railway tracks and Cotswold hills, with a route that ascends to Selsley Common for wide valley views. Water, marshals and first aid are provided on course.

A Trifecta obstacle-course weekend in Henley on Thames featuring Sprint, Super and Beast races plus a kids race along the riverside and town landmarks. Events list 20 to 30 obstacles and show a 4.7 participant rating.

A measured 50 km route from Telford Town Park to Shrewsbury that passes historic sites such as Ironbridge, Buildwas Abbey and Wroxeter Roman City. The event features chip timing, five nutrition stations and a bespoke finish medal.

A multi-distance trail event on Dorset’s Jurassic Coast on 15–16 May 2027, with routes from 10 km to 100 km. The course features marked trails, regular rest stops, medical and massage support, camping options, transfers, and finishers award..

Several distances are available: 5k, 10k and 20k routes around Deddington. The event is open to all ages and organised to raise funds for Deddington Primary School PTA, Deddington PFSU and the Firefighters Charity via Deddington Fire Statio..

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.

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