Trail Running calendar near Chepstow 2026-2027

We have found 488 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

A Backyard Ultra near Crickhowell on a 4.2 mile loop of trail and tarmac, run in hourly yards with a reversed final lap to decide the winner. Medals for 32 miles and trophies for top male and female finishers.

A 50 mile single-loop ultramarathon in the Chiltern Hills around Goring on Thames, with 5,600 ft of climb, five aid stations, full medical cover and a 13 hour finish cut off. The course is mostly trail and fully marked.

A single stage trail running event of about 47 miles along the Cotswold Way National Trail from Chipping Campden to Painswick. The route uses public rights of way, features varied terrain, has food stations and live tracking, and a 15 hour..

An hourly-loop endurance event in Wyre Forest where runners repeat a 6.7 km forest loop until the last runner remains or 24 hours elapse; wooden medals are given to all and a wooden trophy to the overall winner.

A single-stage, approximately 102 mile non-stop trail race along the Cotswold Way from Chipping Campden to Bath, with a 32 hour completion limit, GPX route, live tracking, food stations and medical support.

A community event tracing the River Exe from Exmouth to Dulverton, offering a 43 mile ultra and a non-competitive relay in shorter sections. The run raises awareness of the Exe salmon’s decline and includes local music and ceremonial moment..

A 23 mile trail race on the Quantock Hills where runners compete against horses, plus a Pegasus Challenge four person relay. The event is in Over Stowey on 19 September 2026 with free parking and an age limit of 14 and over.

Fan Brycheiniog is a 15.5 km mountain race in Glyntawe with 840 m of climb. The course runs over rough tracks and open fell and requires navigation and competent mountain skills.

Run Wytham Woods offers 5K, 10K and a 1 mile family fun run through Wytham Great Wood near Oxford on September 19th 2026. The event is organised by the Eynsham community with local partners and a sponsor.

BigSky is the "Air" event in the Classic Element Trail Series on 20 September 2026 at Hyde Common, New Forest. Routes of 18 miles, marathon and 50k run over marked trails with multiple aid stations, mandatory fluid carriage and a bespoke fi..

Experience a multi terrain 10k run through the beautiful South Staffordshire countryside. Finishers receive a bespoke medal and homemade cakes in the heart of Brewood village square.

A looped technical trail in the New Forest at Avon Tyrrell Outdoor Activity Centre where runners choose distances on the day from 5K up to ultra-marathon. Laps are 3.28 miles, with an aid table, on-site facilities and medals for finishers.

A 10 km trail running event at Cannock Chase on 20 September 2026, organized by Wild Deer Events. Entry is listed at £27 and tickets were made available from 18 December 2025.

A scenic, hilly trail half marathon in the Cothi valley near Pumsaint, offering a 13 mile race, a 6.5 mile alternative and a kids race, based at Pumsaint Village Hall on 20 September 2026.

A trail marathon and a 16 mile race around the Purbeck Hills and Jurassic Coast on 20 September 2026, licensed by the Trail Running Association and supporting local charities with required safety kit for participants.

A long running trail race in the Doone Valley, Exmoor covering about 16 km (10 miles) over scenic but hilly terrain. The 37th edition limits entries to 250, requires entrants to be at least 16 and uses chip timing.

A single loop 10K trail run at Woodbury Common on natural trails with climbs and stream crossings. All finishers receive medals and top male and female finishers receive prizes including a donated sports massage.

A functional fitness event at Exeter Arena on 20 September 2026 featuring 10 Xercises with 400 m or 800 m run formats, solo and team entries, age 18 plus, and a live leaderboard with race and division breakdowns.

Black Hill Trail Run in Bere Regis, Dorset features 5 km and 10 km trail races on rural terrain, organised by Bere Regis Scout Group. Course info, results, prize details and charity support are listed on the event pages.

A 50 km looped trail event from a Henley basecamp through Chilterns countryside, with 25 km and 10 km options. The event offers camping, a Saturday meal, covered rest stops, medical and massage support, GPS tracking and a finishers medal an..

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