Trail Running calendar near Upper Woolhampton 2026-2027

Part of a festive Christmas series, the 8 Maids a Milking run offers a choice of distances on a tough, off-road course at Pengethley Manor. With a 7-hour time limit, it's open to both walkers and runners. You can also take part virtually fr..

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 10 mile cross country run featuring the hills and coastal scenery of West Wight. Finishers are rewarded with a unique memento and seasonal refreshments like mince pies and mulled wine in a festive atmosphere.

The 12 Drummers Drumming Run is a festive Christmas series event. Choose from 5k to Ultra distances on a tough off road course at Pengethley Manor. A virtual run option is also available.

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.

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.

Run a flat 19 km route along a historic former railway line through the scenic River Stour valley. This festive trail event is open to all runners including those with dogs and buggies.

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.

Trail races at Wenchford Picnic Site offering a 7 mile course with seven named hills and a 14 mile double lap option. Terrain can be muddy and wet and canicross waves are 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.