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 374 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!
September 2026
A 10 mile, traffic free trail run at Eridge Park on 27 September 2026 featuring steep climbs, muddy sections, route maps and finish-line cake and a pint.
Trail races at Amport Cricket Club with 5k, 10k, 10 mile and canicross on marked multi-terrain routes, cupless stations, first aid and finish-line refreshments.
Trail event near Marlow offering Half Marathon, 10K and a 1K fun run with chip timing, medals and on course water stations.
A Kent LDWA challenge event from Wye Village Hall with 27, 20 or 15 mile routes across the North Downs, close to Wye railway station.
A 5km handicap trail race in Firle on 27 September 2026 with a mostly trail course, a 50 person entry limit, prizes for the top three and village hall facilities.
A timed lap based run at Buchan Country Park in Crawley on 27 September 2026 with distances from 5 km up to ultra and flexible start options. Entry choices include a medal or a lower cost no medal option.
Point to point runs from Central Park, Dartford along the River Darent with 5K, 10K and 18K options plus a finisher medal and post race refreshments.
A mixed terrain 10 km race across the grounds of Highclere Castle on 27 September 2026 supporting Thames Valley Air Ambulance and Newbury AC.
A lululemon Guildford hosted all-levels 5 km trail run at Blackheath Common with music provided, post-run refreshments by Pull & Pour and limited parking.
October 2026
A 7 hour Time Challenge on a signed riverside loop in Staines offering flexible distances from 3 km up to 50 km, with medals, distance pins, aid stations and goody bags.
A timed track event in Walton on Thames on 2 October 2026 offering 6, 12 and 24 hour formats with chip timing, 400 m laps and distance options from 5 km up to 100 mile equivalents. The track is limited to 100 runners at once.
A single loop 100 miles trail race from Plumpton Racecourse across the South Downs, with 12,000 ft ascent, 12 aid stations, a 34 hour limit and a 50 mile qualifier requirement.
Guided 30-mile trail run on the North Downs Way from St Martha's Hill to Box Hill with coach support, group pacing, and nearby transport; entry £55.
Looped night trail races on the South Downs from Plumpton Racecourse, offering 50k, half marathon and 20 mile options with marked course and staffed aid stations.
Trail running from Queen Elizabeth Country Park across the South Downs with five distances from 6 km to 51 km, marked courses and on-course fuel outposts.
A guided 30 mile trail run from St Martha's Hill exploring the Surrey Hills and Box Hill with an experienced ultra runner and coach. Group pace, recommended 22 miles training, cost £55 and an alcohol free beer may be available.
An inflatable obstacle course event at Kempton Park Racecourse on 3 October 2026 with 2.5K, 5K, 10K and 15K options for ages 5 and up.
A family friendly 5k obstacle and colour run near Dorking Surrey in October 2026 with mud, water features and obstacles for ages 6 and up.
Wild Run Cotswolds showcases rugged off road trails on a private estate with fully marked routes, chip timing and a family friendly supporter zone. Entries are limited to 600; choose 10K, half, marathon or the six hour 360 challenge.
Thames Valley LDWA challenge walk in Marlow on 4 October 2026 offering 25 km, 40 km and 50 km routes with checkpoints, mandatory kit and entry limits.