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