Trail Running calendar near Chepstow 2025-2026

We have found 261 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

The Westcountry Ultra 100 Miler is a challenging ultramarathon held in Somerset, UK, combining the Flat 50 and Hilly 50 routes into a 100-mile race with 9,538 feet of elevation. The course features diverse landscapes including canal paths, coastal trails, limestone formations, and Somerset’s highest..

The Sid Valley Ring Half Marathon, held in Devon, England, follows the scenic Sid Valley Ring walking route. The 22km course features an uphill start through quiet country lanes and footpaths, climbing to 236m before descending into the village of Sidbury. Runners pass through picturesque hamlets li..

Endurancelife Exmoor is a challenging trail running event set in the rugged and scenic western area of Exmoor National Park, England. It offers four distances: 10K (6.3 miles), half marathon (13.3 miles), marathon (26.5 miles), and ultra marathon (31.8 miles), each featuring significant ascents and..

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The Tenacious Ten Endurance Challenge is a demanding 10-hour loop race held at Mynydd Troed in the Black Mountains of Wales. Participants tackle a strenuous and technical 3.2-mile (5.1 km) loop featuring a tough climb to the summit with stunning 360-degree views of the Black Mountains, Brecon Beacon..

The Jurassic Coast Ultra Challenge is a premier UK trail running and trekking event held along Dorset’s spectacular World Heritage coastline. Participants can choose from multiple distances including 100km, 75km, 58km, 42km (marathon), 34km, 25km, and a 10km option in Bridport. The full 100km route..

June 2026

BigSea Trails (WATER) is a trail running event held on the Isle of Purbeck, Dorset, starting and finishing on the sandy Knoll Beach at Studland. Part of the Classic Element Trail Series, this race celebrates the element of water with routes that showcase stunning coastal and countryside scenery, inc..

The Two Tunnels Races, held in Bath, UK, offer a unique running experience featuring the longest underground sections in the UK. The course passes through the historic Devonshire Tunnel (408m) and Combe Down Tunnel (1672m), both well-lit and surfaced, providing a flat and scenic route beneath the ci..

Offa's Dyke 15 is a renowned off-road running event held in Hay-on-Wye, Hereford. The race covers a challenging 15-mile course along the historic Offa's Dyke path, offering runners scenic and rugged terrain. Originally popular from 1977 to 2001, the event was revived in 2015 with the help of the ori..

The Centurion South Downs Way 100® is a 100-mile non-stop ultramarathon held annually in Southern England, following the entire South Downs Way National Trail from near Winchester to Eastbourne. The course features rolling hills, ancient forts, picturesque villages, and expansive views across the We..

The Cotswold Way Ultra Challenge is a premier endurance event held in the scenic Cotswolds, UK, featuring multiple distance options including 100km, 75km, 50km, 25km, and a 10km run in Cirencester. Participants can walk, jog, or run at their own pace on a looped route starting and finishing at Ciren..

The Centurion South Downs Way 50km is a challenging non-stop trail race held entirely within the South Downs National Park in Southern England. Starting at Matterley Bowl near Winchester, the 50km course follows the chalk ridgeway and the South Downs Way National Trail, finishing at Queen Elizabeth..

The Cheddar Gorge Challenge is a demanding off-road running event held at Warren Farm, Charterhouse, Somerset, within the stunning Mendip Hills Area of Outstanding Natural Beauty. It offers multiple distances including 1km, 3km, 6km, 10km, half marathon, and marathon, with routes featuring a mix of..

The Jurassic Coast 100 is a challenging ultra running event held along the stunning Jurassic Coast World Heritage site in South West England. Participants can choose from multiple distances: 33 km (Beer to Exmouth), 50 km (Lyme Regis to Exmouth), 70 km (Poole to Weymouth), 100 km (Weymouth to Exmout..

July 2026

The Birmingham Black Country Half Marathon is a running event held in the Black Country area near Birmingham. Organized by StuWeb Events Ltd., it offers participants a half marathon distance of 13.1 miles. The race takes place in a vibrant atmosphere, showcasing the local community and landscape.Whi..

The Severn Challenge is a grueling 220-mile, five-day multistage ultra marathon in the UK, following the longest riverside path from the source of the River Severn in Wales to its mouth. The race is divided into five unique stages ranging from 26 to 59 miles each, with a total ascent of over 3,000 m..

The MTC Hafren Ultra is a challenging 27-mile point-to-point ultra marathon held in Wales, starting at Rhyd-y-benwch picnic area and finishing at the Mid Wales Arts Centre in Caersws. The race begins with a demanding four-mile mountain trek up Plynlimon, known as Wales' most dangerous mountain due t..

The MTC Severn Plod Ultra is a challenging 48-mile point-to-point ultra marathon starting at the Mid Wales Art Centre in Maesmawr and finishing in Shrewsbury. The scenic route passes through diverse landscapes including Holly Bush, Rhyd-y-felin, Dolerw Park, the Gorsedd stone circle, Montgomery Cana..

The MTC Severn Path Ultra is a 59-mile point-to-point ultra marathon starting in Shrewsbury and finishing in Worcester, UK. The mostly flat course follows the River Severn, passing scenic landmarks such as Ironbridge, Jackfield, and Coalport. Runners experience stunning riverside views through towns..

The Black Mountains 50 event, held at Longtown Village Hall in Herefordshire, offers challenging ultra-distance trail runs of 50 and 32 miles, alongside marathon and half marathon options. Set in the stunning Black Mountains, the routes require self-navigation with provided GPX files and maps, featu..

The MTC Severn Way Ultra is a 57-mile point-to-point ultra marathon held in the UK, starting at Travelodge Worcester and finishing at Travelodge Stonehouse. The course follows the scenic Severn Way, passing through towns like Upton-on-Severn, Tewkesbury, Gloucester, and several riverside villages. T..