Trail Running calendar near Upper Woolhampton 2025-2026

Take on a 6 mile self navigation night trail where a written route leads to a secret stop with a cryptic clue for time bonuses. Spot Santas and chocolate, enjoy a refreshment, and bring a head torch, hi viz and phone.

Join the 12 Drummers Drumming Run on 18 December 2025 at Pengethley Manor, Ross on Wye for off road laps through vineyards with a cheeky hill each circuit. Pick a distance from 5k to ultra and enjoy a friendly walkers and runners vibe.

Run the festive Christmas Jubilee River Run 2025, a pop up six hour event on a flat 5.24 mile out and back along the Jubilee River with views toward Windsor Castle. Places are limited and every finisher receives a bespoke medal.

A seasonal 12 km trail run from the Voodoo Keller Bar in Chelmsford that stops at the Chelmsford Brew Co tap room for a brewery drink and a breather. Enjoy a Santa hat, drinks, crisps and a Christmas medal on this social non competitive fes..

Slow and Dirty is a friendly 19k trail run along the converted Somerset and Dorset railway, a flat firm route through the scenic Stour valley and towns. Canicross welcome, with aid stations, refreshments and a medal for a relaxed post run v..

Winter Wanderlust 50km on 21 December 2025 takes you along the scenic North Downs Way from Detling to Wye with about 1,000 m of climbing. Expect varied chalk country terrain, live tracking and hearty checkpoints to keep you going.

Enjoy the Soup Run, a friendly 6 mile multi terrain social run on hilly trails around Bembridge, starting and finishing at the community centre. Entry includes a souvenir, warming soup and roll and a prize draw ticket.

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 early with The Early Christmas Present, a timed loop along the peaceful Stroud Waterways canal where you can run from 5k up to ultra on flat towpath. Limited places, bespoke finisher memento and virtual entry available.

Run a 5 mile night trail through Friston Forest and downland under a head torch, finishing with a festive medal and a drink. Fancy dress and a prize add seasonal fun, this is more adventure than race.

The Die Hard Christmas Marathon and Half Marathon is a festive running event taking place on December 24, 2025, at Caldecotte Lake in Milton Keynes. Participants can choose between a full marathon, consisting of 7.5 scenic laps, or a half m..

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..

Join the Christmas Day Cracker Run, a friendly 7 hour time challenge along the Thames at Wraysbury. Run as many laps as you like from a short 3 km up to marathon and ultra distances, then celebrate with a festive goody bag and medal.

Finish the Crown to Crown series with a festive off road 5 km through bridleways and Willow Park on Boxing Day 2025. Scenic trail loop finishes by the Miller & Carter Crown pub with marshals and on course first aid.

Join the WIM Boxing Day Canter for a lively one hour score orienteering with a mass start and festive bonus controls to chase. Head to Moors Valley Country Park for waterproof maps, SI punching and a fun after Christmas adventure for all ab..

Take on the 7 Sins and Immortal trail runs at Wenchford Picnic Site, a hilly, muddy winter course where 7 or 14 miles test your legs and grit. Canicross waves welcome, so come prepared for wet, icy and steep trails.

Winter X is a scenic trail run through the Meon Valley and sections of the South Downs Way, offering distances of 10 km, 30 km, 50 km and 70 km to suit all endurance levels. Expect marked trails, stocked checkpoints, chip timing and a frien..

Run among the vines at Rathfinny on 28 December 2025 with two 5 km loops across rolling South Downs terrain. Just 75 places and most of the entry fee supports the WOLO Foundation for families affected by cancer.

Join a scenic 10 mile cross country in Hainault Forest on 28 December 2025, three undulating laps from Chigwell Row. Run in tribute to charity and enjoy a festive post Christmas challenge with entries open.

Enjoy mud and festive fun at the Gingerbread Run, a 5 mile off road course through farm tracks and fields near Swindon. Marshalled trails, a halfway prosecco and water stop, edible gingerbread medals and charity fundraising add to the cheer..