Trail Running calendar near Chepstow 2025-2026

Take on The Proud Run at Pengethley Manor on 13 January 2026, an off road lap course through vineyards and rolling hills. Choose distances from 5k to ultra, walkers are welcome and you have a seven hour time limit to conquer your chosen cha..

Take on the Lusty Run at Pengethley Manor in Ross on Wye, an offroad multi lap challenge through vineyards with a hill on each lap. Choose a distance from 5k to ultra and aim to complete your target within seven hours.

On 15 January 2026 tackle vineyard loops at Pengethley Manor in Ross on Wye and pick a distance from 5k to ultra. Off road laps, a hill and 7 hour time limit create a rewarding challenge, with Seven Deadly Sins medals and a virtual option.

Run the Gluttonous Run on 16 January at Pengethley Manor, a scenic off road loop through vineyards and rolling hills with distances from 5k to ultra. Earn a unique Seven Deadly Sins medal or take part virtually.

Haldon Night offers atmospheric night trail racing at Haldon Forest Park on 17 January 2026. Bring a head or chest torch and choose distances from 1K to 10K including a canicross option, with fully marked routes, medals and post race cateri..

The Greedy Run on 17 Jan 2026 at Pengethley Manor near Ross on Wye lets runners and walkers pick distances from 5k to ultra on a tough off road vineyard course with short hills. Entrants must finish within a seven hour limit.

Enjoy gravel trails through ancient woodland in the New Forest at Maverick New Forest Gravel on 17 January 2026. Choose from 22 km, 12 km or 6 km routes with scenic forests, wildlife and a friendly festival vibe.

Dark Skies Series brings winter night trail running to Somerset with three atmospheric events offering 5 km and 10 km routes. Enter individual races or the full series and collect a bespoke wooden finisher's medal to mark the achievement.

Discover the new Cardiff Trail 10k, a scenic 10 km trail run through Fforest fawr near Castell Coch. Expect muddy singletrack, sweeping views and a friendly atmosphere perfect for trail runners looking for a January adventure.

Take on the Riverbank Rollick, a scenic 9.6 mile trail run along riverbanks, woodland and fields with about 80% off road and likely muddy January conditions. Finishers get a bespoke buff and a linkable metal medal in the Thornbury series.

Take on the Envious Run, part of the 7 Deadly Sins series, on 18 January 2026 at Pengethley Manor. Off road laps through vineyards and a rolling hill make this 5k to ultra event a scenic challenge for runners and walkers.

Join the Axmouth Challenge on 18 January 2026 for scenic village runs with distances to suit every runner. Finishers enjoy complimentary refreshments while funds raised support the village hall.

Tackle scenic mixed terrain around Cosmeston Lakes in the CF64 Winter Race, a 6.4 mile off road challenge through woodland, meadows and trails. Join fellow runners on Sunday 18 January 2026 for a spirited winter test of fitness.

Take on the third West Glamorgan cross country race at Margam Park on 18 January 2026, a scenic but testing 5 mile course hosted by Run4All Neath. Pre registration opens 1 January and no on the day entries will be accepted.

Run orienteering in Micheldever Forest on Sunday 18 January with an updated ISOM map and courses for all abilities. EMIT eCards, parking on forest tracks, toilets and nearby pubs make it a convenient winter forest adventure.

Take on the Holly Challenge this January on the leafy lanes of Lightmoor Nature Reserve in Telford, with multiple distance options and medals for every finisher. With only 50 places, this small friendly event offers marshals, an aid station..

Join the Blackdown Beast, a social self guided run across the Blackdown Hills from Dunkeswell on 24 January 2026 with 10 and 16 mile options. Enjoy scenic trails and refreshment stops while helping Macmillan Cancer Support.

Spice Up Your Run Wales, 24 January 2026 at Dare Valley Country Park, is a 7 hour Time Challenge where you pick your laps and earn a Spice Girls themed medal for 3 km or more. Scenic trails, snacks and festival vibes await.

Explore marked trails around Stonehenge in a friendly untimed event for walkers and runners, from 5 km to 40 km. Half the proceeds go to Salisbury Hospice and local athletics. Places are limited and it is cupless so bring your own cup.

Enjoy scenic woodland trails at Moors Valley Country Park with muddy sections, wildlife sightings and two distance options: 10K and half marathon (two laps). Eco friendly event with chip timing, aid stations and limited canicross places.