Trail Running calendar near Brentwood 2026-2027

Join the Christmas Jumper Friday Run on 11 December in Walton on Thames for a relaxed rock up and run along the riverside towpath. Pick 5k to ultra, run laps within a 7 hour window and earn a bespoke finisher medal.

Enjoy a flexible festive run along the River Thames with distances ranging from 3km to Ultra Marathon. This 7 hour time challenge welcomes runners and walkers of all abilities to earn a medal and goody bag.

Join the Mince Pi Run in Guildford for a Pi themed run by the water, with distances from a 1 mile kids fun run to the 3.14 mile loop and laps up to a Pi marathon. Every finisher gets a bespoke Pi Pie medal.

Celebrate the season with forest trail races in Salcey Forest featuring flat 10k, 5k, and junior routes. Enjoy a festive atmosphere with fancy dress prizes and bespoke medals while supporting the charity Shelter.

Experience a festive lap based run through the scenic pathways of Thetford Forest with distances ranging from 5k to Ultra Marathons. Celebrate your finish with a bespoke medal plus complimentary tea and cake at Oak Lodge.

Join a festive Christmas run along the flat Jubilee River. Choose your own distance in this 6-hour timed event on a scenic towpath. All finishers receive a bespoke festive medal.

Enjoy a festive multi terrain race through the muddy woods and farmland of Pett. This family friendly event features distances for all ages and raises money for the housing charity Shelter.

Celebrate the end of the year with this festive event in Bury St Edmunds. Choose between 5k and ultra distances on an undulating course with a seven hour cut off and bespoke medals for all finishers.

Test your endurance at Box Hill with this dawn to dusk trail challenge. Complete as many 10 mile loops as possible before the winter sun sets in this scenic winter event.

Experience a 50 km ultra trail adventure along the North Downs Way from Detling to Wye. This fully marked winter race features historic landmarks, three well-stocked checkpoints, and festive hot food at the finish line.

Celebrate the holiday season with a scenic trail run through Wendover Woods in the heart of the Chiltern Hills. Choose from three different distances with medals and festive treats for all finishers in this December event.

Celebrate Christmas Eve with the Die Hard Christmas races around scenic Caldecotte Lake in Milton Keynes, with marathon and half marathon options. Enjoy lakeside laps, friendly race support and a bespoke finisher medal.

Celebrate Christmas Day with a flexible 7 hour time challenge along the scenic River Thames in Egham. Run any distance from 3km to an ultra marathon and enjoy a unique themed aid station and finishers medal.

Experience a scenic 10 km trail run through the vineyards of the Rathfinny Wine Estate. Support a local cancer charity while enjoying hilly routes and beautiful views of the South Downs National Park.

Winter X is a mid-winter trail-running event in the Meon Valley offering 10, 30, 50 and 70 km on marked public trails with checkpoints and post-event food. Entries for 2025 are closed; a provisional date for 2026 is 28 December 2026.

Winter Runderland in Walton on Thames is a timed lap event on a 5.3 km riverside towpath course. Runners may select distances from 5 km up to ultra, and a lower-cost no-medal entry option is available.

Experience a historic trail race at Box Hill featuring significant elevation and panoramic views of the North Downs. This event offers a 10 km course on rough tracks with dedicated categories for men, women, and children.

Experience a winter trail adventure at the Penshurst Village Cross Country Run. Participants can choose between a standard five mile cross country course or a five mile cani cross run through scenic local landscapes.

Experience an iconic 43 mile ultra marathon journeying from the Buckinghamshire countryside to the heart of London. This season opener features scenic trails and historic canal paths with full GPS tracking and checkpoint support.

The Doughnut Dash is a flexible-distance run along a flat Thames riverside trail. Participants can run from a single lap to ultra marathon distances while enjoying doughnuts. All finishers receive a custom, neon-colored medal.