Trail Running calendar near Chepstow 2026-2027

We have found 404 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

Enjoy a sunset run through the beautiful woodlands and meadows of Coombe Abbey Park. This two lap trail race offers a firm course and a friendly atmosphere for a perfect Friday evening activity.

Experience a varied multi terrain race through the woods and fields of Wiltshire. Runners can choose between a 6 mile course and a 2 km junior race with local refreshments provided at the finish.

This 57-mile point-to-point ultramarathon follows the River Severn from Worcester to Stonehouse. Runners pass through several towns on a comparatively flat course. All finishers receive a bespoke medal and head visor.

Experience a self navigated trail adventure through the Brecon Beacons National Park with distances ranging from a half marathon to an 80 km ultra. Enjoy full support including medical care and tracking across the stunning Black Mountains.

Follow Britains oldest trail through 5000 years of history on the Ridgeway. Choose between 50km or 100km distances and finish at the iconic Avebury Standing Stones with full medical and snack support.

UTMB Index

Experience an obstacle course featuring large scale inflatables in Southampton. Participants can choose between three different distances for a unique physical experience on this bouncy course.

Explore twelve local parishes through the Worcester countryside on circular off road routes ranging from 10 to 40 miles. Walk or run this waymarked event featuring regular checkpoints and a hot meal at the finish.

Run the scenic Shropshire Hills at The Piece of Cake Trail Run in Carding Mill Valley with 10K, half marathon and marathon distances. Enjoy marked trails, aid stations, a finisher medal and a cake competition.

Experience a scenic off road race through the beautiful Otter Valley featuring an undulating 10km and a family friendly fun run. Enjoy a route along the river and old railway line with on site camping available for the weekend.

Join the Butterfly Run at Parc Taf Bargoed with rock up and run starts across distances from 5 km to ultra on a scenic tarmac course with a short riverside trail. Staggered starts, aid stations and an optional supersized spinning medal awai..

This unique 50 km coastal trail run in Dorset features a fun challenge: try to finish before the runner designated as "the Ferry." The scenic out-and-back course passes landmarks like Old Harry Rocks and Corfe Castle. All participants recei..

Experience the scenic Shropshire countryside with the Ludlow10 running event. Choose between a half marathon, 10k, or 5k featuring rural lanes, historic town streets, and undulating off road sections at Whitcliffe Common.

Join this multi lap marathon and half marathon event in Worcester featuring a flat off road course. Run solo or in relay teams with fancy dress and support local stroke recovery charities.

Form a team and take on a 12 hour night trail challenge through the scenic fields and tracks of a private Dorset farm. Enjoy a relaxed atmosphere where you decide your own distance and earn a finisher medal.

Experience a relaxed trail run through the fields and wildflower meadows of a private farm in Dorset. This undulating one lap course is open to all abilities and offers an optional weekend of camping.

Join this 12 hour solo trail challenge at Myncen Farm in Dorset. Complete as many laps as you choose on a scenic farm course featuring fields and dusty tracks with optional weekend camping available.

Explore the limestone cliffs and golden beaches of South Wales in the Gower Peninsula Ultra Challenge. Choose from multiple distances between 10km and 100km with full support and camping at the historic Penrice Castle basecamp.

UTMB Index

Rabbit Run Wales offers stunning trail races on the private Merthyr Mawr Estate. Runners can choose a 12K route over hills, valleys, and sand dunes, or a 40K tour along the dramatic Glamorgan Heritage Coast.

Experience the beauty of the Wales Coast Path with three linear trail races finishing in Cardiff Bay. Choose between 100, 50, or 30 mile distances featuring rugged cliffs, golden beaches, and historic landmarks.

UTMB Index

Test your physical endurance at Huntley Estate with eight strength tests and eight one kilometer off road trail runs. Earn your official time and medal in this outdoor challenge organized by Trimax Events.