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 346 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!
May 2027
Inflatable 5K at Brands Hatch offers laps of 2.5 km with giant inflatable obstacles, multiple distance options, music zones, finisher medals and on course hydration.
A 50-mile point-to-point ultramarathon on the North Downs Way from Farnham to Knockholt Pound with about 5,600 ft of ascent, six aid stations, medical support and a 13 hour cutoff.
Several distances are available: 5k, 10k and 20k routes around Deddington. The event is open to all ages and organised to raise funds for Deddington Primary School PTA, Deddington PFSU and the Firefighters Charity via Deddington Fire Station.
Trail running at Wiston Estate on a marked 10K loop, offering 10K, half marathon, marathon and 100K with aid stations and an event village.
A weekend of waymarked trail runs and walks at Mapledurham House near Reading, featuring ultras, a half marathon and supported marathon-length walks.
A 7 km cross-country fun run at Trenchmore Farm on 22 May 2027 with music, burgers and a free drink for each runner.
A single-lap 50 km multi terrain ultra in Maidenhead on May 22 2027, mainly off road along the Thames Path, Jubilee River and the Green Way. Four aid stations, chip timing, live tracking and on-course nutrition support.
Point to point trail in Surrey offering 62K, 41K and 20K routes plus 2 and 3 leg relays with marked courses, chip timing and an event village with food and partner goodies.
A 5 km obstacle event at War Memorial Park on 23 May 2027 where participants climb, crawl and slide across mixed grass and path terrain; entrants must be 13 or older and a minimum fundraising target of £50 applies.
A 10 km trail race from Marlow Rugby Club featuring riverside towpath, woodland trails, two water refill stations, a branded pint cup and a free drink from Rebellion Brewery.
A guided trail half marathon around the Surrey Hills, about 13 miles from St Martha's Hill in Guildford, following parts of the North Downs Way and notable viewpoints. The run is social in format with a guided pace and evening options.
A point to point 50 km trail race along the South Downs Way from Falmer to Eastbourne with four aid stations, GPS tracking and an 11 hour cutoff that allows walkers.
An 86-mile point-to-point trail race along The Ridgeway from Ivinghoe Beacon to Avebury with GPS tracking, eight checkpoints and mandatory safety kit.
A 60 km point to point ultramarathon along the Ridgeway National Trail from Ivinghoe Beacon to Ridgeway View Campsite, fully marked with open tracking and four checkpoints.
A 24 hour off road trail event on 5 mile loops with solo, pairs and team categories, onsite campsite, parking, caterers and illuminated night routes.
A 13.5 mile single loop trail through the South Downs National Park from Helen Garden, Eastbourne, with about 2,000 ft of ascent and mostly trail terrain.
June 2027
A 24 hour relay at Wasing Park, Reading where Solos, Pairs and Teams run an undulating 8 km trail lap with camping and an on-site event village.
A Star Wars 50th Anniversary weekend on 5 and 6 June 2027 at Caldecotte, Milton Keynes featuring marathon and half marathon races around Caldecotte Lake, unique finisher medals, on-course water and toilets, and time limits for each race.
A 5k obstacle course at Royal Windsor Racecourse with mud obstacles to climb, crawl and slide, mixed tarmac and grass surfaces, staggered wave starts and a minimum age of 13. Earlybird entry prices and a fundraising target apply.
A 5 km obstacle course at Prospect Park in Reading where participants climb, crawl and slide across grassy slopes and woodland. Waves run every 15 minutes and the event is open to people aged 13 and over.