Haywards Heath
Trail Running Calendar near Haywards Heath 2026-2027
Explore the top trail runs near Haywards Heath for 2026-2027! We've gathered 159 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Night orienteering on Wimbledon Common with two technical courses, race centre at The Crooked Billet and online only entry.
27 mile night time group training run at Devil's Dyke with about 1,000 m ascent, guided route and required head torch to practise gear, pacing and night running skills.
Celebrate Fireworks night with a flexible distance run along the flat Downslink trail in Southwater. Choose your distance on the day and run as many laps as you like over seven hours to earn a bespoke medal.
A rolling 10-mile loop around Ashdown Forest across heathland, woodland and sandy tracks with varied climbs and a GPX route for a social trail run.
A 14 mile trail run on 22 Nov 2026 with an initial climb, downloadable route maps, water stations, limited parking and a 50-place field.
Two chip timed races around Wimbledon Common on 22 November 2026, offering a Half Marathon and a 10K on mixed gravel and path terrain with medals and free photos.
A 10 km road and riverside run starting and finishing at Kingston Hawker Centre, using chip timing and offering a finisher medal, refreshments and baggage drop. The event supports Kingston Hospital Charity and notes nearby train and local parking o..
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey with hills, group navigation, kit support, parking and scheduled sunset and night dates.
Complete as many 5 km laps as possible on a marked trail loop from Peaslake Community Hall, with a 2 km ascent toward Pitch Hill and a downhill return. Solo and three-person team entries are available, with refreshments and prizes included.
Trail running from Plumpton Racecourse into the South Downs with three distances, scenic climbs, chip timing and on-course support plus a finisher medal.
A guided 30 mile trail run from Haslemere on the Serpent Trail and Sussex Border Path, led by an experienced ultra runner at a social group pace.
Lap-based timed running on the Downslink at Southwater with distances from 5 km to ultra, flexible start times and a seven hour limit; all participants receive a finisher medal.
A festive Santa Dash in Northchapel on Sunday 29 November with 5K, 2.5K and a toddler scramble, medals for finishers and funds raised for Northchapel Village School.
December 2026
Guided trail run at Box Hill covering 12.5 miles with about 1000 m of ascent across woodland and technical climbs, led at a steady group pace by an experienced guide.
Single loop winter trail ultras on the South Downs from Plumpton Racecourse, offered as 50k, 55 miles and 100 miles with winter conditions and required qualifiers.
A winter adventure race in the Surrey Hills combining trail running and mountain biking with map and compass navigation, multiple time-based options and bike hire available.