Haywards Heath
Trail Running Calendar near Haywards Heath 2026-2027
Explore the top trail runs near Haywards Heath for 2026-2027! We've gathered 146 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
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 race from Plumpton Racecourse through the South Downs with three route choices, notable climbs, coastal views and chip timing.
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.
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.
December 2026
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.
Three single loop winter trail races from Plumpton Racecourse across the South Downs with marked routes, aid stations, GPS tracking and variable winter weather.
A December 10 mile undulating race around Peacehaven with mostly off road sections, marked route, finishers' medal and festive prizes.
Timed lap event at Tilgate Park, Crawley with 5 km laps and distances from 5 km to ultra, a 7 hour limit, and a finisher medal for all participants.
A 200 mile continuous winter trail adventure forming a giant loop across the south of England with a 96 hour time limit and 22500 feet of elevation.
Mince Pi Run on 13 December 2026 at Shalford Park, Guildford offers looped offroad races from 3.14 to 31.4 miles, a Pi marathon option and a one mile fun run shaped like the Pi symbol. The course runs along the water and results are posted online.
A self-navigated festive night trail of about 5 miles through Friston Forest and downland, with medals, a bar perk and a fancy dress dessert prize.
A dawn to dusk trail challenge at Box Hill where runners complete laps of a roughly 10 mile loop with about 2,400 ft ascent per lap; entries include insurance, medical cover and a finisher medal.
Phoenix Running West Sussex stages a timed Jingle Bell Bauble Run on the Downslink at Southwater with 5 km laps, flexible starts and a 7 hour time limit.
January 2027
A 10.000 km trail race around Box Hill with steep climbs and scenic views, registration and parking at Denbies Vineyard. The event includes a kids fun run and a ladies race and uses a B Course around Denbies if Box Hill is unavailable.
An annual New Year five mile cross country in Penshurst village over rolling hills and woodland trails. Open to ages 10 and above with entry fees supporting Hospice in the Weald and awards across junior, local and canicross categories.