Trail Running calendar near Chepstow 2026-2027

We have found 488 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

Choose your own distance on a 3.28 mile out and back along Stroud Waterways canal with a one hour flexible start window and a seven hour maximum for the longest efforts.

Join the Crook Peak Cake Race in Axbridge on Wed 19 Aug 2026 for a spirited 3 mile fell challenge across stunning Somerset hills, finishing with cake and community cheer. On the day entry available for runners aged 14 and up.

Two ultra distances on the Community Forest Path around Bristol: a 45 mile full loop and a 30 mile partial loop. Four checkpoints supply basic food and drink, electronic timing is used and finishers receive a bespoke Green Man medal.

A 7 hour time challenge at Dare Valley Country Park where runners pick their distance from a 3km minimum. The event features a cupcake magnet medal, a baking competition, aid tables with vegan options, and free parking.

A point to point mixed terrain 15 Mile and Marathon following the Old Way from Mayflower Park, featuring coastal landmarks and a short boat crossing of the Hamble River. Finishes are at Titchfield Abbey and Boundary Oak School.

A children's fun run organised by Afan Valley Swimming Club on 23 August, covering approximately 1 mile of mixed grass and tarmac with uphill and downhill sections. Entry includes a finishers' medal and a bag of sweets.

A 10 mile trail race through Radnor forest in Mid Wales on 23 August 2026, held in aid of the Special Care Baby Unit in Hereford. The route reaches Black Mixen at 2130 ft and includes forestry roads, moorland and tree covered single track.

Trail races at Wimbleball Lake on August 28, 2026 offer 10K and 5K distances plus canicross. Courses use off road terrain with lake views and event facilities include medals, photos, showers and camping.

Experience a point to point mountain ultra from the Black Mountains to Cardiff featuring scenic ridges and historic castles. Choose between 33 or 44 mile distances with indoor aid stations and self navigation along the Cambrian Way.

A chip timed, multi-terrain 10 km through Pershore and nearby countryside, finishing in Abbey Park with Pershore Abbey nearby. Entry is online, limited to 325 places and restricted to participants aged 18 and over.

A 7 km fell race with 365 m of ascent in Machen on 31 August 2026. The route runs on steep, loose terrain so trail or fell shoes are recommended and entry is on the day with a £7 fee and age limit over 18.

September 2026

A looped off road ultrarunning event at Top Barn Campsite with 24 hour, 12 hour 50 mile challenge and a new 6 hour option, on a well marked circa 5.6 mile course with camping, water stations and medals.

A scenic mixed terrain race along the Thames at Remenham Farm on 5 September 2026, offering a half marathon, 10K and junior race. The event includes chip timed results, a themed medal, marked course and an event village with food and photos..

A guided 30 mile trail ultra from Knoll Beach, Swanage, tracing the Jurassic Coast and Isle of Purbeck with notable stops at Corfe Castle, Kimmeridge Bay and Old Harry Rocks. Group navigation, kit list and car parking provided; cost £45.

A new *15 mile* trail event in September 2026 on the Rhymney Valley Ridgeway Walk, with 2,267 ft of ascent, mostly off-road terrain, one fully stocked checkpoint and organised entry support from Rudry to Parc Penalta.

Trail running in Carding Mill Valley near Church Stretton with Marathon, Half Marathon and 10K options. The course crosses the Shropshire Hills and The Long Mynd and features marked routes and aid stations.

Enjoy a scenic trail run through the Staffordshire countryside starting and finishing at a canal side pub. This charity event features a 10k route followed by evening food and music.

A series of runs at Westonbirt Arboretum in Sept 2026 and Feb 2027, offering distances from 1 mile to half marathon on solid forest paths, with marked courses, feed stations, event medals and age‑based entry rules.

A long distance 45 mile walk or run across Wales with an 18 hour time limit. The weekend event includes overnight accommodation, coach transport to the start and refreshments along the route.

Point-to-point 50 km ultra on 5 September 2026 between Ramsbury Brewery and Renegade Brewery. Multi-terrain route with about 75% off-road, four aid stations, chip timing, live tracking and a 9 hour cut off.

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