Trail Running calendar near Chepstow 2025-2026

Take on the 5 Golden Rings Run on 11 Dec 2025 at Pengethley Manor near Ross on Wye for a tough off road course through vineyards with a climb on every lap. Distances from 5k to ultra, walk or run, or join virtually for a verified medal.

Brave the 6 Geese a laying Run on 12 December 2025 at Pengethley Manor, Ross on Wye. Choose 5k, 10k, half, marathon or ultra across a very tough off road course with a hill each lap and scenic vineyard views. Walkers welcome.

Take on 7 Swans a Swimming at Pengethley Manor: complete your chosen distance in 7 hours on a 2.5 km off road lap that climbs and winds through vineyards. Walkers and runners welcome and a flexible virtual option is available worldwide.

Choose from three challenging trail distances through Afan Forest, the Rhigos mountains and Coed Morgannwg Way, featuring climbs, long descents and river crossings. Finish at scenic Dare Valley Country Park on 13 December 2025.

Tackle muddy trails and dramatic climbs at the Mortimer Forest Trail Race on 14 December 2025. Choose a testing 10 mile or a shorter 4 mile route over forest paths and High Vinnalls with panoramic views across the Welsh Marches.

Tackle mud, hills and panoramic views at the Mortimer Forest Trail Race with a rugged 10 mile route or a shorter 4 mile option. The full course includes the Big Dippers, a climb to High Vinnalls and a downhill finish over the Welsh Marches.

Join 8 Maids a Milking on 14 Dec at Pengethley Manor, Ross on Wye for a festive offroad run through vineyards and rolling hills. Choose 5k to ultra and finish within a friendly 7 hour limit; walkers and runners welcome.

Take on the 12 Drummers Drumming Run at Pengethley Manor, an off road loop through vineyards and manor grounds with tough hills. Distances from 5k to ultra welcome runners and walkers, with virtual entries and medals available.

Run the spooky A Nightmare Before Xmas Trail half marathon in Bridgend on 20 December 2025, a festive mixed terrain course with hills, mud and scenic road views. Limited to 50 runners, with an eight mile option, mulled wine and a prize for..

Join the Santa Run Wales at Dare Valley Country Park on 20 December 2025 for a family friendly 3 km on scenic footpaths. Enjoy festive music, fancy dress prizes, mince pies and a themed medal at the finish.

Run on Weymouth Beach for The Will Mackaness Trust and help fund youth projects in Weymouth and Portland. Run a festive 5 km in a Santa suit or join the 2 km Chase the Elf for under 14s for a joyful family charity morning.

Celebrate the season at the Slow and Dirty, a family friendly trail race along a converted branch railway near Sturminster Newton, with a level 19k course or 11 mile option. Scenic Stour Valley running, dogs and buggies welcome.

Join the Santa Claws 10km, a festive winter multi terrain cross country run at Renegade Brewery on the Yattendon Estate on 24 December. Expect muddier trails than the summer event, a canicross option and a finisher medal plus a beer or alco..

Tackle the Midwinter Mortimer Trail on 27 December 2025, a scenic mixed surface challenge from Ludlow Castle to Kington through forests, limestone tops and ridges. Choose the 30 mile Ultra or the Croft 15 for a memorable winter adventure.

Take on Plain Crazy Winter, a 12.5 mile road and trail challenge on 29 December with hilly, scenic and wintry terrain and a bespoke finisher medal. The race supports the Royal British Legion and entries are limited, so book early.

The Bell Challenge Day 5, organized by Running Events Devon, takes place on January 2, 2026, in Exmouth at Capel Lane. This 7-hour timed event features a mainly flat, accurately measured 5.3 km out-and-back course on a scenic, disused train..

Run from Budleigh Salterton along the Jurassic Coast and Otter valley with two distances, 13.6 miles or 8.5 miles. Open to runners and walkers, expect mud and hills, friendly marshals and aid stations and a solid oak coaster for finishers.

Take part in Bodenham Bound at Bodenham Arboretum near Kidderminster in January, choosing 5 km or 10 km trail routes. Tackle muddy hills and wintery trails, earn a finisher medal and donut, and support Kemp Hospice and Harkaway Scouts.

Take on upland trails in the Elan and Claerwen Valleys with an annual 12 and 20 mile walking and running challenge. Parts of the route are waymarked and map reading skills are needed; route maps and GPX files are sent to entrants in advance..

Join guided recce runs of the East Devon Round Ultra in early 2026, including the new 25km Quarter route. Free for entrants or a small £3 donation for others, led by Ruby Red Running guides with groups adjusted by ability and pace.