Haywards Heath
Trail Running Calendar near Haywards Heath 2026-2027
Explore the top trail runs near Haywards Heath for 2026-2027! We've gathered 138 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
May 2027
Three Forts Challenge is a Sussex trail running event across the South Downs from Lancing Manor Leisure Centre. It offers a full marathon, half marathon and a 5 mile run, and directs event profits to Ferring Country Centre and local charities.
A guided 12.5 mile trail run around Box Hill that gains about 1000 metres of elevation across woodland, heathland and open fields. Group pace with technical climbs and scrambling and a chance of an alcohol free beer at the finish.
A two day, two person self supported navigation event at Newlands Corner with camping, maps and a points based route across the Surrey Hills.
A point-to-point 50 km ultramarathon from Horsham to Brighton seafront on 8 May 2027, with mixed trails, four feed stations, full course signing and individual or two-person relay entry options.
Inflatable 5K in Guildford on 8 May 2027 offers lap-based inflatable obstacle distances from 2.5k to 15k, music zones, water stations and finisher medals.
Trail races through Rathfinny Wine Estate with single 10.7 km and double 21.4 km loops, marked off-road terrain and chip timing. The carbon neutral event supports the WOLO Foundation and provides aid stations, recycled medals and parking arrangements..
A multi distance trail event around Bewl Water reservoir near Lamberhurst, Kent. Races include 50km, marathon, half marathon and 10km on wooded trails and country lanes with start and finish at the Visitor Centre.
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 7 km cross-country fun run at Trenchmore Farm on 22 May 2027 with music, burgers and a free drink for each runner.
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.
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
Park-based 3k and 5k runs at Dunorlan Park with mixed grass and woodland terrain. The event is organised by Cancer Research UK and includes a fundraising pack and a finishers medal.
A trail half marathon from Chiddingly, Sussex along the Wealdway and Vanguard Way with two checkpoints, chip timing, a five hour limit and a choice to donate instead of a medal.
A 75 mile off road ultra on a one mile loop at Denbies Wine Estate with up to 30 hours to finish, chip timing and multiple concurrent race options.
A 100 mile ultra on a flat one mile trail loop at Denbies Wine Estate offering 12 hour and 24 hour options plus 50, 75 and shorter races.
A 24 hour attended challenge at Denbies Wine Estate in Dorking where runners complete 1 mile on the hour for 24 consecutive hours; onsite tent camping, daytime cafe service and a simultaneous virtual option are provided.