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.
October 2026
An annual 25 km or 50 km countryside challenge in Kent Surrey and Sussex with written route directions, checkpoints, included food and GPX files.
Trail races at Bedgebury National Pinetum & Forest on 18 October 2026, offering half marathon, 10 km and junior distances on traffic free woodland trails.
Timed multi-lap running at Buchan Country Park in Crawley with lap based distances from 5 km up to ultra, flexible start times and a seven hour time limit. Medal and lower cost no medal entry options are offered.
An 8 km trail loop around Herstmonceux with over 70% trail, a 60 person entry limit, prizes for first male and female, and tea and cake after the race.
A trail running weekend at Beachy Head offering Ultra, marathon, half and 10k distances with coastal scenery, staffed aid stations and marked routes.
A social 8 km trail run on the North Downs from Greyfriars Vineyard, finishing with lunch, a glass of English sparkling wine and a guided wine tasting.
An overnight self supported 50 km ultra from East Grinstead to Brighton on 30 to 31 October 2026, in person event with tickets at £14.46 and no refunds.
A relaxed night obstacle run at OPP over two 1.5 km laps, with technical obstacles, surprise elements and a strict headtorch requirement.
November 2026
A 27 mile night-time group training run at Devil's Dyke with about 1,000 m ascent, guided route, head torches required and minimum age 16.
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 14 mile trail race on 22 November 2026 that starts with a climb and follows muddy and chalky descents, with water provision en route and tea, coffee and cake at the finish. Route files and a trail narrative are available to download.
A Half Marathon and a 10k on Wimbledon Common in London supporting Beder, with a trail marked course, course marshals and an event village offering food, drink and partner goodies.
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, 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.