Trail Running calendar near Chepstow 2025-2026

We have found 296 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

The Ragleth Inn race, organized by Mercia Fell Runners, is a fell running event set in Little Stretton, West Midlands. The race features a new route for 2024, covering a distance of 4.4 km with a total ascent of 390 meters. Participants can register on the day or pre-register, with entry fees varyin..

One Fyne Night is a popular running event set in the scenic Fyne Court Estate within the Quantock Hills AONB. Featuring 5km and 10km route options, participants can enjoy a beautiful course that winds through parkland and woods, culminating in a finish at the main courtyard. The event emphasizes sus..

The Beast of Llangattock is a challenging trail running event held in Llangattock, Wales, offering four distances: 10km, 10 miles, 20 miles, and a 32-mile ultra. Starting and finishing at Park Farm, the course features stunning panoramic views of the Black Mountains, Sugar Loaf, and the Brecon Beaco..

The Sunflower Stride is an exciting evening running event held in Dorchester, Dorset, featuring 5k and 10k races through stunning sunflower fields and scenic landscapes. Designed for runners of all abilities, the 5k is open to participants aged 13 and above, while the 10k welcomes those aged 16 and..

The Beast of Bryn is a challenging trail running event held in the scenic Afan Forest Park near Port Talbot, South Wales. Established in 2011 and managed by the Bryn Residents Action Group (BRAG), the 2025 race offers two distances: a 6.5-mile (10.5 km) route with 288 meters of climb, and a longer 1..

The Two Tunnels Races, scheduled for August 17, 2025, in Bath, UK, offer a unique running experience featuring the longest underground sections for each race distance in the UK. Participants can choose from various events, including an ultra marathon, marathon, half marathons, 10km, 5km, and family-..

The Big Pilgrimage is an exciting mixed terrain running event featuring a 15-mile course and a marathon, set to take place along the historic 'Old Way' Pilgrim Trail from Southampton to Canterbury. Participants will enjoy scenic views as they traverse beautiful coastal and countryside paths, with no..

The Black Cattle Ultra Gwartheg Duon is a challenging trail running event held in South Wales, starting at Cardiff Harlequins RFC in Whitchurch, Cardiff. Participants can choose between two ultra distances: 44 miles from Llanthony Priory or 33 miles from Abergavenny. Both routes follow the scenic Ca..

The Summer Green Man Ultra (GMU) is a challenging ultra marathon held near Bristol, UK, featuring two race distances: a 45-mile full loop and a 30-mile partial loop of the Community Forest Path. Both races run clockwise on the same day with shared checkpoints and finish at Ashton Park School. The 45..

The Crickhowell 10km is a scenic race held in August 2025, suitable for runners looking to progress from a 5k. The flat course follows the Brecon & Monmouthshire canal, starting and ending in Llangattock near Crickhowell, with a turnaround at Gilwern. All finishers receive a medal, and there is a wa..

The Pershore Plum 10k is an annual chip-timed running event held in Pershore, Worcestershire, organized by the Pershore Plum Plodders running club. The flat, multi-terrain 10k course starts at Pershore Leisure Centre, follows Pershore High Street, crosses the river into surrounding countryside and f..

Run Winchcombe is a family-friendly running event held at the historic Sudeley Castle in Winchcombe. It offers three race distances: a 1k for children under 11, a 5k for ages 11 and over, and a 10k for participants 16 and older. The courses feature scenic routes around the castle grounds, including..

The Mendip Marauder is a challenging ultra running event held in Somerset, England, featuring two distances: a 30-mile and a 50-mile race. The 30-miler covers the entire West Mendip Way, while the 50-miler includes the East Mendip Way before joining the 30-mile route. The course is notably hilly, wi..

The Henley River Half Marathon, 10k & Juniors event takes place in Henley-on-Thames, UK, on August 30, 2025. This scenic trail run is suitable for both new and experienced runners, featuring routes around Henley-on-Thames with views starting and finishing at Temple Island Meadows, the Royal Henley R..

The Ross on Wye 10K Riverbank Run is a popular running event held in Ross-on-Wye, Herefordshire, featuring chip-timed 10K and 5K races along with a family fun run. The course is flat and multi-terrain, running alongside the scenic River Wye, incorporating river paths with grass and mud sections. The..

The Southampton Running Festival, held on August 31, 2025, takes place in the scenic Southampton Common, a designated Site of Special Scientific Interest in the heart of the city. The event offers multiple race distances including a 5K, 10K, half marathon, and a junior race, catering to a wide range..

September 2025

The RIDUM 2025 is a challenging 30-mile ultra marathon set along the Rhymney Valley Ridgeway Walk in South East Wales. Participants will traverse varied terrain, including lanes, trails, and woodland, with a total elevation of 4,252 feet. The route features notable points such as Mynydd Machen, the..

The Andover Trail Marathon, held in North Hampshire, offers both a full marathon (26.2 miles) and a half marathon (13.1 miles) through scenic trails featuring thigh-burning climbs up to 280 meters and fast downhill sections with views of meadows and valleys. The marathon route follows the Testway to..

The Battle of the Borders is an exciting trail running event set in the picturesque Shropshire Hills, offering participants the choice of a Half Marathon (13.1 miles) or a full Marathon (26.2 miles). This single-lap course begins and ends at Carding Mill Valley, a National Trust area, providing stun..

The Joust 12hr & 24hr is an off-road endurance race held at Top Barn Campsite, Worcestershire (WR6 6NH). The event features a 24-hour race (J24) and a 12-hour 50-mile challenge (J12), with the J24 open to solo runners, pairs, and teams, while the J12 is for solo competitors only. The course is a rou..