Trail Running calendar near Chepstow 2026-2027

We have found 395 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.

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.

Enjoy a festive multi terrain run around the picturesque Chasewater Reservoir with distances ranging from a Junior Run to 20 km. This undulating course features professional timing, bespoke medals, and a friendly atmosphere.

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.

Experience a scenic 8 mile multi terrain circuit in Freshwater featuring 900 feet of ascent and coastal views. This hilly course takes runners past Tennyson Down and Alum Bay with professional timing and finisher rewards.

Enjoy a unique trail running event where you ride a heritage steam train to your start line before racing back to Minehead along the beautiful Somerset coastline and Quantock Hills.

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

Experience the rugged beauty of the Gower Peninsula with a self navigation half marathon or marked trail runs of 10km and 5km. Enjoy coastal paths and woodland trails starting from the scenic Oxwich Bay.

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..

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.

Experience the landscape of the Shropshire Hills through a series of trail runs and walks ranging from 10 km to 80 km. Enjoy local food and historical landmarks while supporting educational charity programs.

Experience a guided 18 mile adventure across the Malvern Hills ridge and surrounding woodlands. This social group run features over 1300m of elevation and stunning panoramic views at a non competitive pace.