Trail Running calendar near Chepstow 2026-2027

We have found 430 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

A trail ultra in Hampshire on 4 April 2026 with 50 mile and 40 mile route options along the Testway. Aid stations every 10 miles, marshals and an on course medical team provide support and an optional shuttle returns runners to the start.

A 30 mile circular ultra on 4 April 2026 around Monmouth, covering parts of the Three Castles Walk and Offa's Dyke Path with 4,258 ft of elevation and two fully stocked checkpoints.

Test your endurance with this 12 hour Backyard Ultra format race featuring a 4.167 mile loop through the Purbecks. Run as an individual or in a team while enjoying the scenic Jurassic Coast and a lively event village.

A Backyard Ultra at Chilton Manor Farm featuring private wildlife trails, fields, woodland and a summit at Bugmore Hill Trig Point. The event uses a camp hub for rest and refuelling between roughly 6.7 km laps and offers marked routes and a..

Experience the unique challenge of racing on the firm sands of Pendine Beach. Choose from five distances ranging from 5k to an ultra marathon on a course famous for land speed records.

Multi-distance Easter races take place around Chasewater Reservoir at Chasewater Country Park, offering a junior run and distances to 20k. The event features route maps, bespoke medals, free photographs and volunteer support.

Join this Easter Monday tradition in Berkshire featuring a 10km off road course through local woodlands. Participants can choose between a standard foot race or a dog friendly canicross event starting from the Mortimer Fairground.

An 8 miles single lap trail on the Isle of Wight with about 900 feet of ascent visiting Golden Hill Fort, Alum Bay and Tennyson Down. Limited to 175 entrants, the race uses timing chips and offers age category prizes and a finisher souvenir..

A trail running event that uses a steam train on the West Somerset Railway to move runners between Minehead and Bishops Lydeard. Three distances are offered and all routes finish outside Minehead Station.

Experience a scenic mixed terrain race along the banks of the Thames in Henley on Thames. Choose from a half marathon, 10K, or junior race starting at the iconic Temple Island Meadows.

Three coastal trail races of 32.5, 18.5 and 10 miles follow the Wales Coast Path along the Vale of Glamorgan, with waymarked routes, staffed checkpoints, and coach transport for the linear course finishing at Ogmore-by-Sea.

UTMB Index

Trail races at Oxwich Bay on the Gower Peninsula include a self navigation half marathon plus marked 10 km and 5 km routes, with chip timing, finisher medals, water stations and checkpoints.

Follow the South West Coast Path for 22 miles from Exmouth to Seaton featuring 4000 feet of ascent. Choose between solo, relay, or half distance options for this established trail race along the Devon coastline.

A 15 miles fell race on the Mendips with over 2,000 feet of climbing and a fully marked Category B course. The route starts on Warrens Hill and finishes at Fairlands School where tea and cake are provided.

Tackle the Kymin Dash, a 7 mile road and trail race from Monmouth that climbs to the Round House for panoramic views before descending through fields and bluebell filled woodland. Enjoy a lively finish at Monmouth School Sports Club with Ki..

Wild Horse South Wales 200 is a 200-mile trail ultramarathon through South Wales. The route links historic paths like Offa's Dyke and the Beacons Way, finishing at Worm's Head on the coast. This point-to-point adventure offers a multi-day c..

A short fell race on 15 April 2026 at Forest Glen, Wellington covering 4.5 km with 247 m of climb. Pre-entry and on the day entry are available, junior races run before the senior event and the race holds FRA insurance.

The MTC Gelert is a 47-mile ultramarathon along Wales's scenic National Cycle Route 8, from Barmouth to Llanidloes. It is also the third day of the CYMRUN multi-day challenge. The event has a strict 4 mph pace requirement and provides a bes..

A six hour event at Kingsbury Water Park where participants complete as many 3.3 mile laps as they can. The mostly flat route passes five ponds and a river over grass, gravel and short asphalt sections.

Experience a scenic 40 mile ultra marathon along National Cycle Route 8 from Glasbury to Merthyr Tydfil. This quadrennial event offers a well supported route through the Heart of Wales with unique finishers medals.