Trail Running calendar near Chepstow 2025-2026

We have found 273 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

The Medal Mix Challenge Day 1, organized by Running Events Devon, takes place near Capel Lane, Littleham, Exmouth on November 29, 2025. This 7-hour timed event welcomes runners and walkers of all abilities to complete as many 5.3 km laps as possible on a scenic, undulating out-and-back course along..

The Medal Mix Challenge Day 2, organized by Running Events Devon, takes place near Capel Lane, Littleham, Exmouth on Sunday, 30th November 2025. This 7-hour timed event features an accurately measured 5.3 km out-and-back course on a scenic, undulating old disused train line, fully paved and classifi..

Winter Bumble Bimble is a social winter trail run in the Bromsgrove countryside, starting and finishing at the Park Gate Inn on Kidderminster Road. The winter event offers a 5-mile option (11 miles in summer) through Dodford countryside, a valley, and Nutnells Wood, with marshals, arrows-marked rout..

RTT Afan Forest 10k & 5K is organised by Aspire X Events and takes place at Bryn Bettws Lodge, Pontrhydyfen, Port Talbot SA12 9SP. The next scheduled race date is 30/11/2025. The event runs on trails in Afan Forest and offers two separate distances. The organiser hand-picks trails and provides..

December 2025

The Telford T50 Trail Run is a winter 50-mile trail challenge from The Unicorn Inn in Little Dawley, Telford. For 2025, it follows the Telford T50 pathway, looping from Ironbridge to the Wrekin through industrial areas in Shropshire. The event features a marked course and four aid checkpoints with f..

Endurancelife Dorset runs in Swanage along the Jurassic Coast Path, a World Heritage-listed coastline since 2001. The event offers four distances—10K (6 miles), half marathon (13.1 miles), marathon (27 miles), and ultra (37.2 miles)—with substantial climbs (774, 1,719, 4,692, 7,027 ft) on an extreme..

UTMB Index

Secret Santa Figgy Pud 14km, Turkey Ten Miles & Half Marathon Du Mulled Wine is a trail event from Cwmdu Village Hall near Crickhowell, Powys. Distances are 14km, 10 miles and a Half Marathon. The courses head west toward Bwlch Mountain and follow the Beacons Way, with the Half Marathon routing via..

Limitless Trails’ Secret Santa Series heads to the Brecon Beacons, starting and finishing at Cwmdu Hall, Powys. Distances offered are 14 km, 10 miles, and 13.1 miles, beginning from Cwmdu along Beacons Way toward Bwlch Mountain, with the half marathon following Cockit Hill for lake views before turn..

The event is scheduled for 6 December 2025 at Old Fowler Barracks, Ludgershall Road, Ludgershall, SP11 9RR. It takes place on Salisbury Plain, which is described as the largest military training area in the UK and possibly Europe. The route follows well established footpaths and byways and includes..

Cardington Cracker is a 14.5 km fell-running race in Cardington, Shropshire, hosted by Telford Athletic Club at Cardington Village Hall. The route climbs about 793 m and is largely marked and marshalled, with a notable stretch down The Lawley and a few road crossings. It is limited to 250 online ent..

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..

Full MontyCute 10 trail race is a tough, mostly off-road 10.6-mile course in Ham Hill Country Park near Stoke-sub-Hamdon, Somerset. The route climbs 11 hills and threads through Montacute, St Michaels Tower, Ladies Walk, Witcombe Valley, and Parkland, finishing back at the Ham Hill Information Centr..

The Allsorts Tinkley Gate Santa Dash is a festive, family-friendly running event held at the scenic National Trust Tinkley Gate site in Woodchester, Gloucestershire. Participants can choose between a 5km off-road trail or a shorter 2.5km route, suitable for younger runners. The event welcomes runner..

Set in South Wales, Celtic Trail Races offers three trail challenges: the Ultra (34 miles), Marathon (26 miles), and Half Marathon (13 miles). The routes wind through Afan Forest and the Rhigos range, finishing along the Coed Morgannwg Way with dramatic views of the Brecon Beacons, Black Mountain, S..

Mortimer Forest Trail Race is a multi-terrain event staged by Ludlow Runners in Moor Park School, Ludlow, on 14 December 2025. The programme offers two courses: a 10-mile route over challenging forest tracks including the notorious Big Dippers and a climb to the top of High Vinnalls, finishing with..

A Nightmare Before Xmas Trail ½ Marathon, staged by Mad Running Junkies, takes place at the Bridgend Miniature Railway Centre in Aberkenfig, Tondu, near Bridgend (CF32 9BZ). The course blends the Hateful Eight 8‑mile route with a further 5+ miles of challenging trail, totaling around 13 miles of mix..

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-themed 19-kilometer trail race held in Sturminster Newton, Dorset, following a flat, hard-surfaced route along a former railway line known as the Somerset and Dorset (S & D). Despite its name, the course is fast and clean, ideal for runners of all abilities, including..

Santa Claws 10km is a winter cross-country event organized by Racing Line Running, held at Renegade Brewery in the grounds of the Yattendon Estate, Berkshire. The course is a multi-terrain 10km, with a Canicross 10km option for runners with dogs. It delivers a scenic, muddy yet beautiful route throu..