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.
June 2027
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.
A trail running event at Cranleigh Showground on Saturday 19 June 2027 with routes from 5 km to 53 km across Surrey hills and forests. Fully marked courses, varied outposts, free parking and an event village with food and a non alcoholic beer.
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.
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.
July 2027
A 5 km cross-country fundraiser at Stanmer Park on 3 July 2027, featuring grassy start and woodland terrain with steep inclines, organised by Cancer Research UK.
Race for Life Brighton at Stanmer Park offers 10k, 5k and 3k routes across fields and woodland with mixed surfaces and inclines. The event includes fundraising support, on-site facilities and a finisher medal.
Group guided 10 km trail run across the boardwalk and heathland of Thursley National Nature Reserve with evening and night options, car parking and a post-run alcohol-free beer.
A Pretty Muddy 5k at Tilgate Park with obstacles on woodland and lakeside paths, a double lap course and a minimum age of 13.
September 2027
Guided 10 km trail run around Silent Pool near Guildford, following parts of the North Downs Way and Netley Heath forest. Sessions run at dusk or at night with headtorches in a led group and a recommended pace of about 10 min per mile.
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.
October 2027
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.
A 5 mile night trail run in Litlington with a self navigated Strava GPX route, Halloween fancy dress and timed results for runners aged 18 and over.
December 2027
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 guided 30 mile trail run from Haslemere that follows sections of the Serpent Trail and Sussex Border Path, aimed at runners attempting an ultra for the first time. Group pace, varied terrain, cost £55.
July 2028
A continuous 200 mile trail across the South Downs with marked support, 14 aid stations, three sleep stations and a 100 hour time limit.