Trail Running calendar near Chepstow 2026-2027

Join a weekend fell and trail running retreat in the Black Mountains, Wales from 27 Feb to 1 Mar 2026 at Dinas Castle Inn. Guided runs on the Dragons Back ridge, skills coaching and bunkhouse accommodation make for an inspiring weekend for..

Take on the spectacular South West Coast Path, including the iconic Durdle Door and Kimmeridge Bay. Choose from 10 km, 27 km, or 50 km distances on a course featuring steep elevation and off-road terrain. The event includes fully stocked ai..

The Castle2Castle #Ultra is a 32-mile point-to-point run from Welshpool's Powis Estate to Chirk. The route features a mix of flat trails and gentle hills. An optional shuttle bus helps with logistics.

A point-to-point, fully marked long-distance race along the Taff Trail from the Brecon Beacons to Nantgarw, covering about 70 km. The course mixes upland trails and valley cycle paths, with six checkpoints and a Merthyr drop bag for mid-rac..

Two winter mountain races between Brecon and Cardiff. The Brecon to Cardiff Xtreme is about 75 km (47.5 miles) over 11 summits with roughly 2680 m ascent, while the Taff Xtreme Marathon covers the second half at about 26.2 miles and 1300 m..

Weymouth Bay 10K is an accurately measured road race along Bowleaze Cove with an out and back layout and two laps near Pleasure Pier. The event offers medals and trophies, on-day registration, and supports Margaret Green Animal Rescue.

The Imber Ultra is a 33.5-mile multi-terrain charity run circling the Imber Range Perimeter Path. Starting in Westbury, the 2026 event will be run clockwise. It's an affordable, TRA-licensed event with awards for top finishers and age categ..

A trail running event at Breamore House offering 5k, 10k, 5k Canicross and a half marathon on mainly rural trails, with marshals, aid stations and finisher medals.

Tackle mud, hills, and a stream crossing on this annual multi-terrain challenge over approximately 6 miles at Baggeridge Country Park. It's organised by the cardiac rehabilitation charity Action Heart. A friendly, gritty event with a 90-min..

Celebrate St David's Day with a flexible 7-hour time challenge run in Wales' scenic Dare Valley Country Park. Choose your own distance on well-maintained footpaths and earn a medal for any run over 3 km. Free parking, an aid station, and go..

Push your limits at Haldon Horror on 1 March 2026 in Haldon Forest Park with 3 hour, 6 hour or 12 hour formats on 5 mile laps and canicross options. Medals, live GPS tracking and free photos await, just bring a headtorch.

The Brave returns to Exmouth for a scenic cliff and beach run. Choose between a 5km or 10km mixed-terrain course starting at Sideshore. The event supports a local community project focused on youth and the coastline.

A trail championship at Matterley Basin near Winchester on 4 March 2026, offering 10 km and 20 km races run on 5 km laps with mass starts and on-course water stations.

The MTC Winter Green Man Ultra offers 30 and 45-mile loops on Bristol's Community Forest Path. With four checkpoints and pacers guiding various finish times, it's a winter ultramarathon challenge. All finishers receive a medal and technical..

Trail running at Hinton Admiral Estate on 7 March 2026 with 21.6 km, 15 km and 10.1 km routes; running, canicross and hike options through woodlands, heath and meadows. Finishers receive a medal, a drink and goodies.

Tackle 580m of ascent on this challenging 7.8km fell race through Carding Mill Valley. Part of the Shropshire Winter Series, it features rocky tracks and steep descents. Full mandatory kit is required for all participants.

Run a flexible-distance coastal challenge with views of the Isle of Wight. Choose from 5K to ultra-marathon on a mixed-terrain, lap-based course. Enjoy an aid station and a relaxed start window.

Choose from a marathon, 20 miles, half marathon, 10km, or a 1 mile fun run at the Larmer Tree Gardens in Dorset. All finishers get a colourful medal.

A women's trail running event at the Culden Faw Estate near Henley on Thames. It features three different trail distances: 13 km, 6.5 km, and a 3 km option.

A flexible three day running event based at The Unicorn Inn in Telford with options of 8 miles, a half marathonish distance or a full marathon across one, two or three days, and a ticket range from about £42 to £115.