Trail Running calendar near Chesham 2025-2026

We have found 381 Trailruns within 80 miles of Chesham. See below where and when you can find the races.

Middlesex Cross Country Championships return to Hillingdon Sports and Leisure Centre in Uxbridge on Saturday 13 December 2025. Youth and senior races from 2k to 12k, chip timed, open to clubs, schools and individuals.

'Twas The Run Before Christmas at Brandon Country Park on 14 Dec 2025 invites runners to tackle four or six hour timed challenges on a 5.3 km multi terrain lap through Thetford Forest. Bring your own bottle and earn a finisher medal.

Mince Pi Run - races of 2 decimal places is a 14 December 2025 off-road event at Shalford Park, Guildford. Participants choose from 3.14 to 31.4 miles (1–10 laps) on a scenic, mostly flat course with one or two hills. A Pi marathon option a..

Let it Stow is a festive half trail marathon in Stowmarket, featuring 13.1 miles of footpaths, woodland and country lanes for a scenic run. Finishers earn an eco friendly medal, top runners get trophies and photos capture the day.

Join the Salcey Forest Christmas Race on 14 December 2025 for 10k, 5k or a 1.2km junior fun run on mostly flat forest trails. Fancy dress, festive prizes and bespoke medals, with proceeds supporting Shelter.

Celebrate the season with MV Festive Orienteering at Buchan Country Park on 14 December, exploring woodland trails around the lakes. Courses for all levels, family friendly and every finisher gets a warm drink and mince pie.

Night street orienteering in Colchester on 17 December from the Berechurch Arms. Choose a 3.4 km short or 5.4 km long course, use MapRun or printed maps and hunt controls by torchlight for a fun, technical evening.

Run the Search For Santa night trail on 17 December, a 6 mile self navigation adventure with hidden Santas, chocolate and a secret clue stop that can earn time bonuses. Costumes and quirky humour are encouraged and prizes await.

Join the ZigZag 2025 Christmas Canter in Bury St Edmunds on Dec 20 for festive 5k, 10k, half, marathon or ultra on scenic rolling roads. Limited to 300 runners, it offers medals, aid stations and included parking for a cheerful festive run.

Join the 20th Christmas Pudding Dash in Pett near Hastings for festive, family friendly cross country races across farmland and woods. Multiple distances, medals, prizes and mince pies make this muddy, fun run a great seasonal tradition.

Join the Chelmsford Brew Co 12ks of Christmas for a festive 12k trail from the Voodoo Keller Bar to the brewery and back, finishing in the town bar. Expect drinks, a Santa hat and prizes for the best Christmas fancy dress.

Take on Winter Wanderlust, a 50 km trail ultramarathon along the scenic North Downs Way from Detling to Wye. Enjoy rugged chalk downs, three well stocked checkpoints, hot food and a finisher medal for those who make the cut.

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.

Join the Festive Friston Forest, a five mile night trail through Litlington woods and downs on 22 December 2025. This friendly timed adventure features festive fancy dress, a finisher medal and a pint or hot drink back at the pub when you r..

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..

Run on Christmas Day along the Thames at the Christmas Day Cracker Run, a 7 hour time challenge where you choose laps from a 3 km minimum to ultra distances. Finishers get a medal and festive food and treats at race HQ.

Join the festive Runners v Riders at Friday Woods, Colchester, where runners and cyclists battle muddy off road trails for the Markham Cup. The senior race is about 3.5 miles, with free junior sign ups on the day.

Join Pitsea Running Club for the Crown to Crown Boxing Day 5k, an upbeat off road loop through Willow Park starting and finishing at Westley Heights Country Park. A friendly community race perfect for festive miles and post Christmas fun.

Winter X is a scenic trail running day from Meonstoke with routes along the South Downs Way. Distances from 10km to 70km, with checkpoints, chip timing, marshal support and a finisher shirt.