Trail Running calendar near Chepstow 2025-2026

We have found 298 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

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 multiple laps of a 3.3-mile off-road loop featuring crushed stone paths through tranquil woods, open grassland, and alongside calming waters. The course is mostly firm and suitable for al..

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 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..

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 features full and sprint distan..

The Dalwood 3 Hills is a popular multi-terrain running event held in Dalwood, near Axminster, Devon. Returning in 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 Doddle" fun run..

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 (43-mile) ultra running race held annually along the scenic Taff Trail from Brecon in the Brecon Beacons National Park to Nantgarw near Cardiff. Now in its 12th year, this fully marked, one-way race features diverse landscapes, starting with dramatic m..

The Brecon to Cardiff Xtreme is a challenging 75-kilometer mountain ultramarathon traversing 11 major peaks between Brecon and Cardiff, featuring approximately 2,680 meters of ascent. This winter race demands advanced mountain running skills and fitness, with a linear route starting at Brecon's cana..

The St David's Day Dragon Run 2026, hosted by Saturn Running, takes place in the scenic Dare Valley Country Park, Aberdare, Wales. Celebrating the patron saint of Wales, this event offers a unique 7-hour time challenge where participants can choose their running distance, starting from a minimum of..

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 annually around Bristol, UK. Scheduled for March 7, 2026, it offers two distances: a 45-mile (72 km) full loop and a 30-mile (48 km) partial loop of the Community Forest Path. The course runs anti-clockwise with 4 well-stoc..

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. Runn..

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

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

The Nant Yr Arian Silver Trail Races, set in the stunning Cambrian Mountains, offer participants a choice of challenging routes, including a Half Marathon and a 10km race, suitable for both beginners and experienced runners. The event also features children's races for various age groups. With fully..

Winter's End - 50 Mile Ultra & Marathon is a scenic trail running event held along the South Downs Way National Trail, starting near Arundel, West Sussex, and finishing in Winchester, Hampshire. The event features a 50-mile ultramarathon and two marathon options covering either the first or second h..

The Forest of Dean Spring Trails Half Marathon is a scenic 13.1-mile race held annually in the Forest of Dean, starting and finishing near the Speech House Hotel. The course features well-maintained woodland trails with gentle inclines, offering a multi-terrain experience through beautiful forest la..

The Way of the Dead is a challenging 50k running event traversing Dartmoor from east to west, organized by Wild Running. Participants can compete solo or in pairs, with live GPS tracking and three checkpoints that also serve as feed stations. The route features minimal ascent of 1389 meters but requ..