South East (England)
Trail Running Calendar South East (England) 2026-2027
Explore the best trail runs in South East (England) for 2026-2027! Our updated list features 363 exciting trail runs across the region. Find your next trail run in South East (England) below and join the trail community at these great events!
December 2026
A dawn to dusk trail challenge at Box Hill where runners complete laps of a roughly 10 mile loop with about 2,400 ft ascent per lap; entries include insurance, medical cover and a finisher medal.
A timed festive event on the Itchen Way in Winchester with flexible rock up start times, a measured out-and-back course, lap options up to ultramarathon distance, and a bespoke finisher medal.
A roughly 4 mile trail run around Pett on 19 December 2026 with a marshalled, fully marked course, Christmas finisher medal, prizes and post-race tea and cake.
A 50 km trail ultra along the North Downs Way from Detling to Wye with about 1,000 m of ascent, three checkpoints and mandatory kit requirements. The route passes Boxley Warren, Thurnham Castle, Lenham Cross and the Wye Downs.
Trail runs at Wendover Woods on 20 December 2026 include a Santa Mile plus 5 mile and 10 mile races, with medals, merchandise and festive refreshments for finishers.
Phoenix Running West Sussex stages a timed Jingle Bell Bauble Run on the Downslink at Southwater with 5 km laps, flexible starts and a 7 hour time limit.
Community Santa fun run in Lewes on 20 December 2026 offering 5 km, 10 km, 15 km and a junior 1 mile Elf Run with proceeds to Friends of Lewes Victoria Hospital.
A lakeside Christmas event in Milton Keynes offering marathon and half marathon options with 7½ and 3½ clockwise laps of Caldecotte Lake. Finishers receive a bespoke medal and the event is held under 100 Marathon Club rules.
A 10 km trail run and Canicross 10 km on December 24th around Yattendon Estate with hilly woodland trails, a medal, mince pie and a pint cup included.
A 7 hour Time Challenge along the River Thames in Staines offering distances from 3 km up to 50 km, medal and goody bag, plus an optional Christmas dinner at The Last Hop.
A charity off-road three mile run in Saltwood on 26 December 2026 that usually attracts over 1,000 entrants, with medals for all finishers and several entry options.
A charity event on 27 December 2026 near Waterlooville with a 10k mixed road and trail run and a 5k walk, raising funds for Rowans Hospice.
A low key multi-lap half and full marathon along the River Thames in Walton on Thames on 28 December 2026. The UKA certified flat towpath course awards medals to all finishers and has limited places.
Winter X is a mid winter trail running event in Hampshire's Meon Valley offering 10 km, 30 km, 50 km and 70 km routes on public trails including sections of the South Downs Way. Checkpoints, marked routes and a rock memento are provided.
Trail event at Butlers Lands Farm with water crossings, Roman Walls and fields, offering 10K and 10 Mile options plus finish line mulled wine and mince pies.
Off road races at Longmoor across sand dunes, ponds and mud with single and two lap options and medals for all finishers.
January 2027
A 10.000 km trail race around Box Hill with steep climbs and scenic views, registration and parking at Denbies Vineyard. The event includes a kids fun run and a ladies race and uses a B Course around Denbies if Box Hill is unavailable.
An annual New Year five mile cross country in Penshurst village over rolling hills and woodland trails. Open to ages 10 and above with entry fees supporting Hospice in the Weald and awards across junior, local and canicross categories.
Kickstart the New Year with a 10.5 mile trail run over Beachy Head followed by a random distance draw to complete a unique virtual mileage challenge.