Haywards Heath
Trail Running Calendar near Haywards Heath 2026-2027
Explore the top trail runs near Haywards Heath for 2026-2027! We've gathered 145 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
May 2027
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 on a fully marked 10K loop at Wiston Estate, with distance options from 10K to 100K solo or team and regular aid stations.
A 10th anniversary half marathon and new 10k in Chislehurst that explores local green spaces and raises funds for The Maypole Project.
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 from Falmer to Eastbourne along the South Downs Way, with over 3,500 ft of climb, four aid stations and GPS tracking.
A 13.5 mile loop from Eastbourne across the South Downs to Friston Forest, the Seven Sisters and Beachy Head, with about 2,000 feet of ascent and basic race support.
June 2027
Community 3k and 5k runs at Dunorlan Park on mainly grass and woodland terrain with some inclines and limited general parking.
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.
Run one mile on the hour for 12 consecutive hours at Denbies Wine Estate with chip timing, a finisher medal, camping and a simultaneous virtual option.
Timed event at Denbies Wine Estate on 20 June 2027 using a 1 mile loop; runners choose distances from 1 mile to ultra and run laps within a six hour limit.
Multi-distance evening run at Cowdray Estate on 25 June 2027 offering 3 km, 5 km, 10 km and dog-friendly CaniRun options plus series medals and on-site refreshments.