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.

Endurancelife Dorset offers a challenging trail running event set along the stunning Jurassic Coast Path near Swanage. Participants can choose from four distances: 10K, half marathon, marathon, and ultra, with ascents ranging from 774 to 7,027 feet, making it a tough trail runner's paradise. The cou..

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The Cardington Cracker is a popular fell running event organized by Telford Athletic Club, taking place in Cardington, Shropshire. The race covers a distance of 14.5 km with a total ascent of 793 meters, making it a challenging course, especially in December's conditions. Participants must pre-regis..

The Chasewater Christmas Pudding Dash is a festive running event held at Chasewater Country Park in Staffordshire. Offering 10k, 5k, and junior race options, the course features mostly flat, slightly undulating compacted trails around the scenic Chasewater Reservoir. The 10k race consists of two lap..

The New Forest Xmas Trails is a festive trail running event hosted by BigFeat Events, set in the picturesque New Forest National Park. Participants can choose from four distances: 15K, 30K, Marathon, and 50K, all on challenging yet runnable off-road courses. The event begins at Holmesly Campsite, of..

The Celtic Trail Races, held annually at Dare Valley Country Park in Aberdare, South Wales, offer a festive trail running experience with three distances: a 34-mile ultra, a 26-mile marathon, and a 13-mile half marathon. The routes traverse the Afan Forest, Rhigos mountain range, and the Coed Morgan..

The Mortimer Forest Trail Race will take place in Ludlow on Sunday 14 December 2025.

The Nightmare Before Xmas Trail ½ Marathon is a challenging trail running event held at the Bridgend Miniature Railway Centre in Bridgend, UK. Participants face a tough course starting with the "Hateful Eight," an 8-mile route featuring mixed terrain including a steep hill, scenic road sections, and..

The Christmas Carol Bobble Hat Run, organized by Saturn Running, takes place in the scenic Dare Valley Country Park in Aberdare, Wales. This inclusive event welcomes runners and walkers of all abilities. Participants can choose their distance within a 7-hour time challenge, with a minimum of 3km and..

The Slow and Dirty is a festive 19-kilometer trail race held in Sturminster Newton, Dorset, following a level, hard-surfaced route along a former railway line known historically as the Somerset and Dorset or "Slow and Dirty." The course offers scenic views along the River Stour valley, passing resto..

The Winter Woolly 10km is a popular trail running event held annually on December 24th at Elstree School in Upper Woolhampton, Berkshire. Now in its sixth edition, the race features a scenic multi-terrain course covering 10 kilometers with 80% off-road paths, including lanes, footpaths, trails, wood..

The Midwinter Mortimer Trail is a challenging trail running event held in Herefordshire, England, featuring two main distances: approximately 30 miles (Ultra) and 15 miles (Croft 15). The routes traverse the scenic Mortimer Trail from Ludlow Castle to Kington (Ultra) and from Aymestrey to Kington (C..

The Plain Crazy (Winter) is a challenging 12.5-mile trail run held in Warminster, featuring a hilly and potentially snowy course that is scenic yet desolate and windy. The event supports The Royal British Legion Poppy Appeal and offers prizes across various age categories for both male and female ru..

January 2026

The Bell Challenge Day 5, organized by Running Events Devon, takes place on January 2, 2026, in Exmouth at Capel Lane. This 7-hour timed event features a mainly flat, accurately measured 5.3 km out-and-back course on a scenic, disused train line surfaced entirely with tarmac, classifying it as a roa..

The Walter Raleigh Round Half Marathon is a scenic 13.6-mile race starting and finishing in Budleigh Salterton, England, the birthplace of Sir Walter Raleigh. The course traverses quiet back lanes, unsurfaced county roads, hidden footpaths, the Otter Valley, High Peak, the Jurassic Coast, and a dism..

Haldon Night is a winter night trail running event held at Haldon Forest Park near Exeter, Devon. It features single-loop courses of 10K and 5K distances, with the 5K open to children aged 8 and above if accompanied by an adult. The event also offers kids' races: a 1K for ages 3-7 and a 2K for ages..

The Cardiff Trail 10k is an exciting running event set against the stunning backdrop of Castell Coch. Scheduled for January 18, 2026, this newly introduced race offers participants a unique blend of competition and natural beauty, making it an ideal choice for both experienced runners and newcomers...

The Dirty Devil Stampede is a challenging and muddy running event held at the Bovington Tank Range in Bovington Lane. Participants can choose from 5k, 10k, or 15k distances, with a special Dark 10k race taking place at dusk on a different course. The race takes place on an army training ground, offe..

The Crocodile Challenge is a 6-hour running event held at Ryton Pools Country Park near Coventry in Warwickshire. The course is a runnable, relatively flat 3.3-mile loop around pools and open pasture with crushed stone paths and some minor rises. Participants can complete as many laps as they wish w..

The Holly Challenge is an exciting running event organized by How Hard Can It Be Events, set to take place in Lightmoor, Telford. Participants can choose from four distances: 5K, 10K, Half Marathon, or Marathon, making it suitable for runners of all levels. This event marks the first race of the yea..

Saturn Running's "Spice Up Your Run - Wales" is a fun and inclusive running event held at Dare Valley Country Park in Aberdare. Participants can walk or run a minimum of 3km, with options to complete laps of approximately 7km each, allowing distances up to 50km, including half-marathon, marathon, an..