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!
May 2027
Multi-terrain running festival at The Springs Resort and Golf Club with 2 km kids run, 5 km, 10 km and 10 mile options plus chip timing and finisher medals.
A four month summer series at Dinton Pastures with 5km, 10km and a 2km kids race on flat traffic free lakeside trails, featuring medals, chip timing and on course marshals.
Obstacle-course weekend in Henley-on-Thames on May 15 and 16 2027 with Sprint 5 km, Super 10 km, Beast 21 km and kids races by the River Thames.
An inflatable obstacle course at Brands Hatch offering 2.5K laps with giant inflatables, music zones, on-course water, and medals for all participants.
A 50 mile point to point trail race along the North Downs Way from Farnham to Knockholt Pound with 5,600 ft of climb and six fully stocked aid stations.
Looped event at Denbies Wine Estate offering distances from 5 km to ultra, run as many 5.3 km laps as desired within a 7 hour limit.
Community 3k and 5k events at North Walls Recreation Ground, Winchester on 16 May 2027 with mixed grass and tarmac surfaces and wheelchair access with assistance.
Runs of 5k, 10k and 20k through the parish of Deddington, open to all ages and raising funds for local school groups and the Firefighters Charity.
Looped trail event at Wiston Estate with a marked 10K circuit and distances from 10K to 100K, plus aid stations, a dedicated 100K area and on-site camping.
A coastal relay event on 16 May 2027 based at The Valiant Sailor and Lilly Roo's in Capel Le Ferne, CT14 0AT, organised as a team relay along the coast.
A 7 hour timed running event along the River Thames in Staines offering distances from 3 km up to ultramarathon with medals, distance pins, goody bags and aid stations.
Mixed terrain off-road races in the Chiltern Hills with 1 km, 10 km and a half marathon, raising funds for Bledlow Ridge School.
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 along the Thames Path and Jubilee River with four aid stations, chip timing, live tracking and race photos.
Trail races on the Fox Way around Godalming, Surrey, offering 62K, 41K and 20K routes with cupless aid stations and chip timing.
Multi terrain marathon and 16 mile runs across the Berkshire Downs with aid stations, timing, a finisher mug and proceeds to Berkshire Women’s Aid.
Stand & Deliver challenges runners to repeat a scenic 4.2-mile loop at The Dell in 12-hour, 6-hour or Backyard formats, with solo, pairs and teams of three options.
A muddy 5k obstacle event at War Memorial Park with climbing, crawling and sliding, organised by Cancer Research UK and linked to fundraising.
Guided 13 miles through the Surrey Hills from Guildford, run as a steady group with trail sections, car parking and nearby train access.