Trail Running calendar near Chepstow 2025-2026

We have found 335 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

Take on the Beer Blazer on 17 May 2026, a multi terrain run along the Jurassic Coast with cliff top views and pebble beach sections. Enjoy race day refreshments and a BBQ while supporting Beer Primary School.

Run 145 miles non stop along the Grand Union Canal from Birmingham to Little Venice on a fully waymarked towpath. Limited to 100 starters with supported or unsupported entries and a 45 hour cutoff, it is a classic long distance challenge.

Run the Taunton Trail 10K or Half Marathon on 24 May 2026 at Taunton Rugby Football Club for an ultra flat, fast route along scenic waterways. Friendly marshals, well stocked feed stations and finisher medals make for a rewarding day.

Take on the Rocky at 50 Run Wales, a relaxed 7 hour time challenge at scenic Dare Valley Country Park where you pick your distance from a 3 km minimum up to 50 km. Finishers earn themed medals and enjoy tasty aid station treats.

Run through Southampton Common on 31 May 2026 amid woodland, lakes and wetlands. Choose half, 10K, 5K or junior distances and enjoy a lively event village with food, freebies and a sustainable focus.

June 2026

Take on the VOGUM 40 mile ultra along the Wales Coast Path on 6 June 2026, enjoying beaches, cliffs and coastal castle views from Porthcawl to Penarth. Fully staffed checkpoints and no time limit make this a stunning and supported adventure..

Join the Divorce Day Defib Fundraiser on 6 June 2026 for scenic laps from The Unicorn Inn across the Ironbridge and along the Silkin Way. Choose 8 mile, 16 mile or marathon options and embrace the fun of fancy dress with top hats and tiaras..

Run the Brecon Beacons at Midnight Mountain Marathon on June 6, 2026, starting in daylight and finishing under the stars, so some may need a torch. Take part in Marathon, Half Marathon or Bergen pack races and earn a medal and a mug of tea.

Join Blended Trails Backyard Ultra at Chilton Manor Farm for a test of endurance: run a one hour loop each hour until only one runner completes a lap. Enjoy private trails, camping, great fuel stations and a winner takes all prize.

Take on the Oner Ultra Trail Run, an epic 85 mile coastal ultramarathon along the scenic Dorset Coast Path on 6 June 2026. Runners must complete the route within 24 hours for a true test of endurance.

Run through two lit railway tunnels beneath Bath on routes from short fun runs to ultra distances. Starts and finishes at family friendly Brickfields Park and each entry supports Sustrans, making it a memorable community day out.

BigSea Trails WATER brings runners to the Isle of Purbeck, with a beach start and single lap routes past Corfe Castle, Kimmeridge Bay and Old Harry Rocks. Distances from half marathon to 54k ultramarathon offer sweeping coastal views.

Run along the shoreline from Bournemouth Pier toward Boscombe on sand and over groynes, choosing 5K or 10K routes with lovely sea views. Great for all abilities, with marshalled support and a relaxed coastal vibe.

Offa's Dyke 15 returns to Hay on Wye on Saturday 13 June 2026, offering a scenic 15 mile challenge with individual and relay entries. With roots from 1977 and a popular 2015 relaunch, this classic race is staged by Tempo Events.

Take on the South Downs Way 100®: a stunning 100 mile nonstop trail test from Matterley Bowl to Eastbourne across chalk ridges and big climbs. Expect remote views, lively aid stations and a classic long distance challenge for runners.

Take on the South Downs Way 50km on 13 June 2026, a scenic trail challenge through the South Downs National Park organized by Centurion Running. Tackle 50 km of rolling ridges with 1200 m climb, aid stations and a lively finish.

Tackle the scenic Cotswold Way from Cirencester with distances from 10 km to 100 km and options for walkers, joggers and competitive trail runners. Enjoy a buzzing basecamp with camping, full support and memorable finishers goodies.

UTMB Index

Explore coastal and inland trails along the Jurassic Coast with distances from a fun 7 km up to a 23 km half marathon. Registration at the venue, full course marking, outpost snacks and a metal finisher medal make this a scenic, dog friendl..

Run the iconic Cheddar Gorge from 1 km to marathon, or try the Omnium combining sprint, climb and middle distance challenges. Wave starts, waymarked scenic but rocky courses, food stations and medals for 6 km and above.

Tackle scenic trails on Watership Down at the Hampshire Hoppit on Sunday 14 June 2026, with marathon, half marathon and 10K routes that climb some of Hampshire's highest points. Enjoy finishers medals, a keepsake beer glass and real ale in..