Trail Running calendar near Chepstow 2025-2026

Warm up your winter with the Winter Hot Chocolate Series, three friendly cross country races around Bramshill Plantation based at St Neot's School. Enjoy chip timing, themed medals and hot chocolate treats, plus a fun 1 mile kids race.

Take part in Festive 5 on 11 Jan 2026, a 5 mile off road run along the River Avon through Fladbury and Lower Moor. Organised by Friends of Fladbury, this fundraiser offers free cake, spot prizes and supports local community projects.

Explore scenic off road trails around Farley Mount near Winchester with 12 km and 21 km options, chip timing and a finisher medal. Start and finish at Sparsholt College with great parking and welcoming race day support.

Enjoy scenic off road laps around Pengethley Manor and its vineyards, with a cheeky hill and rolling ups and downs. Choose distances from 5k to ultra, walk or run at your pace within a seven hour limit and earn a finisher medal.

Take on the 7 Deadly Sins 7in7, a seven day challenge at Pengethley Manor in Ross on Wye from 12 to 18 January 2026. Run or walk varied distances each day on a hilly 2.5 km off road lap and collect a unique medal daily.

The Proud Run at Pengethley Manor on January 13 invites runners and walkers to tackle laps through vineyards and a testing hill, choosing distances from 5 km to ultra. Off road, scenic and inclusive, entrants must finish within seven hours.

Lusty Run at Pengethley Manor invites runners and walkers to tackle scenic off road laps through vineyards and a testing hill. Choose distances from 5k to ultra or take part virtually with a personalised bib and medal.

On 15 January 2026 the Angry Run invites runners to tackle an offroad looped course at Pengethley Manor, choosing distances from 5k to ultra. Expect rolling hills, vineyard trails and a friendly festival atmosphere.

Tackle the Gluttonous Run at Pengethley Manor, part of the 7 Deadly Sins series on 16 January 2026. Pick 5k to ultra and brave a tough off road loop through vineyards with a hill each lap, or opt for the virtual challenge.

The Greedy Run at Pengethley Manor on Saturday 17 January 2026 invites runners and walkers to choose from 5k up to Ultra on an offroad loop through vineyards and rolling hills. Race day has hot drinks, food, free parking and a finisher meda..

Run a winter night trail at Haldon Forest Park on 17 January 2026 with 5K, 10K, 10K canicross and fun kids 1K and 2K. Fully marked and chip timed with medals, food, photos and post race beer, so bring a head or chest torch.

Run the Maverick New Forest Gravel at Holmsley Campsite, Burley, through ancient woodland with 6 km, 12 km and 22 km routes. Enjoy scenic gravel trails, some mud and short climbs for a true forest challenge.

Join the Axmouth Challenge around picturesque Axmouth Village Hall with quirky start and finish at the village phone box. Choose from 1 to 9 mile routes and enjoy free post race refreshments while supporting the village hall.

Tackle the Envious Run on 18 January 2026 at Pengethley Manor, a scenic offroad loop through vineyards with a hill each lap. Choose any distance from 5k to ultra or run virtually in January for a finishers medal.

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..

Take on the Riverbank Rollick a scenic 9.6 mile off road trail run along riverside paths, through woodland and a stream crossing. Earn a metal finisher medal that links to two other Thornbury Running Club races for a collectable series.

Take on the Crocodile Challenge at Ryton Pools Country Park, a timed six hour loop where you run as many laps as you like around scenic pools. Canicross and rucking welcome with dogs on short leads; finishers get a medal and a portion of fe..

The Holly Challenge is a multi-distance race organized by How Hard Can It Be Events, held at Burroughs Bank, Lightmoor, Telford, TF4 3QS, within the Lightmoor Nature Reserve. Runners can choose 5K, 10K, half marathon, or marathon distances...

Take on Spice Up Your Run Wales, a relaxed 7 hour time challenge at scenic Dare Valley Country Park where you pick your distance from 3 km upwards. Enjoy countryside laps, snacks and medals for finishers, with fancy dress warmly encouraged.

Join the social, self navigated Blackdown Beast, a scenic cross country run from Dunkeswell Airfield supporting Macmillan Cancer Support. Expect village hall and pub refreshment stops, stunning hills and 10 or 16 mile options.