Trail Running Calendar South East (England) 2026-2027

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.

Join the 20th Christmas Pudding Dash near Pett, Hastings for a festive muddy cross country with a looped main race of about 4.2 miles plus a fun run and children's scurry. Enjoy medals, photos, fancy dress prizes and support for Shelter.

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.

A seven hour Time Challenge along the River Thames at Wraysbury Skiff and Punting Club in Egham, with distances from 3 km up to 50 km. Finishers receive a Christmas themed medal, distance pins for half marathon and above, and a goody bag.

A cupless charity run through Rathfinny Wine Estate on 28 December, comprising two 5 km vineyard loops with limited places and a donation of £8 from each £12.50 entry to the WOLO Foundation.

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.

A January trail race around Box Hill with a measured 10.000 km course, 473 m ascent and 335 m descent. Registration and parking at Denbies Vineyard; earphones are not permitted and an alternative Denbies course is used if Box Hill is closed..

Join the Penshurst Village Cross Country Run on Sunday 3 January 2027 for challenging 5 mile and canicross races over scenic local trails and open ground. Enjoy a friendly village atmosphere and a great day out for runners and their dogs.

A 43 mile point to point ultra from Wendover to Little Venice, London, mixing country trails and Grand Union Canal towpath. The race includes GPS tracking, five checkpoints, baggage transfer, mandatory kit and an 11 hour cutoff.

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.

A countryside trail run around Farley Mount in Hampshire with two route options, including a Half Marathon. The course is rolling with tree-lined sections and vistas, starts at Sparsholt College with ample parking, and offers finisher medal..

This trail run through Moors Valley Country Park offers a half marathon and a 10K on woodland gravel paths. It's a dog-friendly event with chip timing and an eco-medal. Be prepared for muddy sections and inclines on the scenic course.

A 10 miles and 5 miles trail race at Pippingford Park Manor with hard packed trails, about 1568 ft of climbing and panoramic views. The event includes bespoke medals, cash prizes for podium finishers and free parking.

The Hibernal Hills 50 mile is a season-opening ultra on a 53-mile loop from Queen Elizabeth Country Park. With 6400 ft of climb on 99% trail, it's a UTMB Index race requiring a marathon qualifier. Runners are supported by six aid stations a..

Run 50k on the fully signed trails of the North Downs Way and through Norbury Park's ancient woodland. This trail ultra features four well-stocked checkpoints and is based from Denbies Wine Estate. Finishers are awarded a commemorative meda..

The Serpent Trail event offers a scenic run through the South Downs National Park on 3rd July 2027. Choose from five distances, from 10km to 100km, on a trail passing heathlands and woodlands. The event includes transport to the start and w..