Trail Running calendar near Chepstow 2025-2026

Tackle the wild trails of May Hill with muddy climbs and an open summit offering panoramic views. Pick the shorter course or the longer Mayhem loop, or join the canicross for a lively weekend of cross country fun.

Explore the Shropshire Hills from Carding Mill Valley with marathon, half marathon or 10k routes across The Long Mynd and National Trust terrain. Enjoy stocked aid stations, a medal and a fun cake competition after your run.

Run the Starburster twilight trail at Hurn Forest, starting from St Leonards Cricket Club, with 5 mile or 10 mile out and back options under sunset skies. Bring a head or chest torch, enjoy the forest trails and support Forestry England.

Oxford Town v Gown 2026 brings a lively interclub orienteering clash on Saturday 31 January, with starts in University Parks and assembly at St Anne's College. Expect a 5 to 6 km course studded with artificial barriers that will reshape you..

Join the DirtRun Dudmaston 10k on 1 Feb 2026 for a scenic off road 10 km through Comer Woods at Dudmaston Estate. Enjoy a finisher medal and goodie, with category prizes including real ale for top performers.

Take on Round 4 of the West Glamorgan XC League at Kenfig Nature Reserve on 1 February 2026, a scenic 4.2 mile cross country hosted by Cornelly Striders. Entries are capped so book in advance to guarantee your place.

Hit the trails at Haldon Forest Park for Haldon 5K & 10K on 1 February 2026, with scenic routes, finisher medals and free race photography. Open to runners and canicross participants and forming part of the PGE trail running championships.

The Westonbirt Arboretum Winter Night Race is a unique running event set in the stunning National Arboretum, featuring over 2,500 tree species. Participants can choose between 5km and 10km routes, which offer a beautiful and varied landscap..

Enjoy a winter run through Westonbirt Arboretum's stunning tree collections on solid underfoot trail style paths. Distances of 5 km and 10 km suit all paces. Tickets are sold out.

Explore the stunning Portland Coastal Ultra Trail along the South West Coast Path with 10k, half and full marathon options. Enjoy rugged sea views, chip timing and a finisher medal; GPS route download required.

Run a scenic 27 km loop from Sidmouth Watersports Hub, visit four trig points in order and tackle about 900 m of climb along coastal cliffs. Supportive local event with a slate finisher medal and proceeds to Cardiac Risk in the Young.

Join the Wye Valley Brewery Muddy Woody on 8 February 2026 for a muddy, runnable trail romp of about 6 miles through forestry and stiff hills. Limited to 300 places, entrants get a bespoke Muddy T shirt and chip timing.

Take on the Wiltshire 10, a scenic 10 mile route from Melksham to picturesque Lacock, with medals for all and prizes in veteran categories. Entry capped at 300 with on site facilities and water stations.

Tackle scenic bridleways and ancient woodland trails at The One in the Woods, Henley, with a half marathon, 10k and family Little Sprinters 1k. Enjoy a lively event village and a finisher medal to celebrate your run.

Tackle the Purbeck Hill Challenge 2026, a one day navigation run across the Purbeck Hills and Jurassic Coast from Knoll Beach. Choose four distances, solo or pair, and tackle orienteering through wild coastal terrain.

Take on the rolling countryside at Dalwood 3 Hills on 15 February 2026, with 10 mile, 5 km and 3 km trail routes featuring hills, mud and river crossings. Friendly village HQ and rustic parking promise a proper off road winter challenge.

Join the SMaRTT Smasher on 15 February 2026 in Calne for a flat, traffic free 10k along the national cycle network to Stanley and back. A lively 1 mile fun run for under 17s adds family fun and all finishers get a memento.

Run Brimscombe's canal towpath at the Back to the 80s timed event, choosing any mix of 2.62 mile laps to make 5k to ultra distances. Enjoy a relaxed one hour start window, seven hour limit and a bespoke finisher medal to mark your effort.

Choose distances from 9 miles up to a 37 mile ultra on the Winter Railway Ultra, a scenic route along the River Severn on a disused railway between Ironbridge and Bridgnorth. Enjoy regular aid stations, great riverside views and nearby vill..

Experience Bath's Two Tunnels from Brickfields Park, running through lit, traffic free tunnels and scenic river and trail sections. Distances range from 500 m to a 50 km ultra and marathon, but entries are sold out.