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 418 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
Free Sunday trail runs every two weeks from Surrey Trek and Run through the Surrey Hills and North Downs with multiple distances and places limited to ten per leader.
A guided 10 km trail run through Ashdown Forest followed by an hour of yoga at Tranquility Yoga Studio, with tea and light snacks in Heron's Ghyll on Dec 6, 2026.
A 200 mile continuous loop from Juniper Hall across the North and South Downs with a 96 hour limit, GPX navigation and three major aid stations.
Timed lap event on a flat 5.3 km riverside course with distances from 5 km to ultra and a seven hour maximum time limit.
A festive time challenge along the River Thames in Staines where runners choose distances from 3 km up to 50 km. The event is signed, offers medals and pins, aid stations and goody bags.
A point to point winter trail race of 100 miles from Amberley Museum to Juniper Hall across the South Downs and North Downs with a 35 hour cut off.
An offroad multi-lap event at Shalford Park, Guildford offering runs from 3.14 to 31.4 miles, a Pi marathon option, a 1-mile kids run, and bespoke Pi Pie medals.
A festive, untimed fun run at Denbies Wine Estate with Santa suits provided, a 5 km mixed-surface route, charity support and post-run mulled wine and mince pie.
Community festive run at Stocklund Square on 13 December 2026 with 5 km and 10 km options, medals and fundraising for Knowle Park Trust Cranleigh.
A 5 mile night trail run in Friston Forest with a self navigated GPX route, festive fancy dress, finisher medal and a bar exchange for returned race numbers.
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.
Dawn to dusk winter trail at Box Hill, Dorking with a 10.1 mile loop and 2,400 ft climb per lap. Runners may stop after any completed loop.
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 festive trail run around Pett with a fully marked course, finisher medals, prizes and tea and cake at Pett Village Hall.
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 in the Chilterns offering a family Santa Mile plus 5 and 10 mile races with chip timing, medals, and finishers refreshments.
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 small, social 10 mile winter trail run across the South Downs with a custom event T shirt and festive snacks, limited to 25 runners.