Trail Running calendar near Chepstow 2025-2026

We have found 269 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

The Stonehenge Stomp is a popular walking and running event organized by the City of Salisbury Athletics & Running Club, held near the iconic Stonehenge site. Participants can choose from fully marked trail distances of 5 km (family-friendly), 10 km, 20 km, 30 km, or 40 km, all offering scenic views..

The Moors Valley Wildwood Trail Series Half Marathon & 10K is a trail running event held at Moors Valley Country Park & Forest in Dorset. Scheduled for January 25, 2026, it offers two distances: a half marathon consisting of two laps and a 10K with one lap. The course features scenic woodland trails..

The Icing On The Cake is a thrilling trail running event set in the picturesque Shropshire Hills, featuring both half (13.1 miles) and full (26.2 miles) marathon options. Scheduled for February 1, 2025, participants will navigate a scenic route that showcases the rugged beauty of the area, starting..

February 2026

The Squirrel Challenge is a 6-hour running event held at Daventry Country Park, United Kingdom. Participants run or walk as many 3.3-mile laps as they wish within the time limit, making distances flexible from just over 5K to over 80K. The course features mostly crushed stone paths through tranquil..

The Westonbirt Arboretum Winter Night Race is an exciting running event set in the stunning National Arboretum, featuring over 2,500 tree species. Participants can choose between 5km and 10km routes, which showcase the arboretum's diverse landscapes and solid terrain, providing a unique blend of tra..

The Exeter Half Marathon, organized by Exeter City Community Trust, is a popular running event held in Exeter, UK. The race features a two-lap, 13.1-mile (half marathon) course starting from Piazza Terracina, Haven Road, and follows a scenic route along Exeter’s historic Quayside and Riverside Valle..

The Portland Coastal Marathon is an exciting running event set to take place at the Weymouth and Portland National Sailing Academy. Scheduled for February 9, 2025, it features a full marathon, half marathon, and a 10k, catering to runners of all abilities. Participants will navigate the scenic South..

The Westonbirt Arboretum Winter Day Race is a scenic running event set in the stunning National Arboretum, featuring over 2,500 tree species. Participants can choose between a 5km or 10km race, with routes that showcase the beauty and diversity of the arboretum's landscape. The event is designed to..

The Trails & Tarmac Backyard Ultra, organized by Limitless Trails, is a challenging endurance event held near Crickhowell in the scenic Black Mountains, Powys, UK. Participants run a 4.2-mile (approximately 4.17 miles in some editions) loop combining equal parts trail and tarmac, featuring mostly fl..

XTERRA Matterley is an off-road sporting event held at the scenic Matterley Basin in Hampshire, United Kingdom. Scheduled for February 14-15, 2026, it offers a variety of race formats including duathlons and trail runs suitable for athletes of all levels. The duathlon races feature distances such as..

The Dalwood 3 Hills is a popular multi-terrain running event held in Dalwood, near Axminster, Devon. Scheduled for February 15, 2026, it offers three distances: a challenging 10-mile course featuring hills, mud, and river crossings; a 5km "Dalwood Dash" with similar terrain; and a new 3km "Dalwood D..

The Two Tunnels Races, taking place in February 2026, offer a unique running experience through Bath's historic underground tunnels, the longest of their kind in the UK. Participants can choose from a variety of distances, including ultra marathons, half marathons, 10km, 5km, and family-friendly Col..

March 2026

The Brecon to Cardiff Classic is a 70-kilometer ultra running event held annually in Wales, following the scenic Taff Trail from Brecon in the Brecon Beacons National Park to Nantgarw near Cardiff. The fully marked, one-way course showcases diverse landscapes, starting with dramatic mountain scenery..

The Brecon to Cardiff Xtreme is a challenging 47.5-mile (75 km) winter mountain ultramarathon held in Wales, running from Brecon to Cardiff over 11 peaks including Pen Y Fan, the highest peak in South Britain. With approximately 2,680 meters of ascent, the course demands excellent winter mountain ru..

The St David's Day Dragon Run 2026, organized by Saturn Running, takes place in the scenic Dare Valley Country Park in Aberdare, Wales. This 7-hour time challenge allows participants to run distances of their choice, starting from a minimum of 3km. The course features well-maintained footpaths with..

The Weymouth Bay 10K is a scenic charity fun run held in Weymouth, Dorset, starting at Bowleaze Green near the Riviera Hotel. The course is an accurately measured out-and-back route featuring two laps, extending towards Pleasure Pier and returning via Overcombe. The mostly flat road terrain (88%) of..

The Winter Green Man Ultra (Winter GMU) is a challenging ultra marathon held near Bristol, UK, featuring two distances: 45 miles and 30 miles. The 45-mile race is a full anti-clockwise loop of the Community Forest Path starting and finishing at Ashton Park School, with 945 meters of elevation gain...

The Hateful 8 Loopy Ultra is an endurance running event held at Bridgend Miniature Railway in Aberkenfig, Bridgend, South Wales. Participants tackle a challenging 9-mile mixed terrain loop featuring a tough hill, scenic road sections with stunning views, and a technical downhill forestry trail. The..

The Hannington Hike will take place in Hannington on Sunday 8 March 2026.

The Centurion Hundred Hills 50km is a scenic trail ultramarathon held in the Chiltern countryside, England, starting and finishing at the historic 850-year-old Stonor Park near Henley-On-Thames. The race features two distinct 25km loops, covering 50 kilometers with approximately 4,000 feet of elevat..