Trail Running calendar near Haywards Heath 2025-2026

The Castle Trails 30km is a scenic point-to-point trail race in Kent, launching in 2026 as part of the Three Castles 50km Ultra weekend. Starting at Little Fant Farm near Maidstone and finishing in Tonbridge, the course follows the River Medway, passing historic sites like East Farleigh’s stone brid..

The Three Castles 50km Ultra Marathon is a scenic race held in Kent, England, starting in Rochester and finishing at Tonbridge athletics track. The flat course follows the River Medway, passing three medieval castles, charming villages, and lush countryside along the Medway Valley Walk. Runners expe..

Beat The Sunset 50km Ultra Marathon takes place in Maidenhead, Berkshire, starting and finishing at Summerleaze Park (NMCC Sports Club). The 50-kilometre, multi-terrain course is about 75% off-road and features around 235 metres of ascent. It is a fully signed, single-loop route that traverses the T..

The Circuit du Sore Legs is a unique running event held at Wodson Park Sports and Leisure Centre in Ware, Hertfordshire. Participants run on a traffic-free 400-meter athletics track, with distances ranging from 5k to a 6-hour challenge, including half marathon, full marathon, and 50k ultra options...

Surrey Hills Half Marathon is a guided trail half marathon based in Guildford, Surrey, covering about 13 miles. The route travels through the Surrey Hills, with highlights including St Martha's Church and hill, the village of Shere, and views from Newlands Corner and Hackhurst Downs, including secti..

The Sundowner Marathon is a unique running event held in Purleigh, Chelmsford, England, featuring a scenic course that passes along canals, over waterfalls, through vineyards, woodlands, and coastal saltmarshes. This marathon offers a distinctive experience by starting early on a summer evening and..

Dell 10km takes place in the Hampshire countryside at Dummer Down Farm, hosted by Dummer Down Brewery. The event features a 10km multi-terrain route (and a Canicross 10km) that weaves through private farmland, woodlands, fields and local lanes, finishing back at the brewery taproom. The course is ab..

Centurion Running’s South Downs Way 50km is a 50km non-stop trail ultramarathon through the South Downs National Park. The course starts at Matterley Bowl near Winchester and finishes in the Event Field at Queen Elizabeth Country Park, following the chalk ridgeway along the South Downs Way with expa..

South Downs Way 100 is a 100-mile non-stop ultramarathon along the South Downs Way National Trail, from Matterley Bowl near Winchester to Eastbourne. In its 15th year, Centurion Running's event follows the chalk ridgeway across rolling hills, ancient forts, pretty villages and expansive views of Sou..

Bewl Water Summer is a bi-annual trail-running event at Bewl Water Visitor Centre near Lamberhurst, Kent. The series offers ultra (50 km), marathon (26.2 miles), half marathon (13.1 miles), and 10 km, all starting and finishing beside the Visitor Centre. Courses follow the clockwise Bewl reservoir c..

YHA 14 mile trail run is a 14-mile off-road event held near Southease along the Lewes–Seaford line in East Sussex. The course begins with a climb and includes muddy sections, chalk descents, and rewarding views, designed as a single-loop trail with several elevation gains. A trail narrative and link..

Wendover Woods Half Marathon & 10k, staged in Wendover Woods, Upper Icknield Way, Aston Clinton, Buckinghamshire, offers trail runners a forest challenge. The course comprises a hilly 10k multi-lap route through Wendover Wood forest, with Half Marathon option also on offer. Runners can expect scenic..

Solstice at the Lakes is a timed trail running event held at Leybourne Lakes Country Park in Kent, featuring 6-hour, 12-hour, and 24-hour race options. Participants can compete solo or in teams (pairs or up to four runners) on a flat, fast, and scenic 2.5km loop combining trail, gravel, and tarmac s..

Beyond Trails London is a trail running event set in Greater London, offering two distances: a 25km trail and a 55km ultra. Both routes follow parts of the Capital Ring footpath, showcasing iconic sights such as Eltham Palace, Wimbledon Common, and Richmond Park, alongside hidden trails, parks, wood..

P24 - The Longest Attended Day takes place at Denbies Wines Estate, London Road, Dorking, Surrey, on the summer solstice weekend of 20-21 June 2026. The concept is simple: run 1 mile on the hour for 24 hours on a flat-ish, off-road 1-mile loop through the estate. Attended participants benefit from f..

The Centaur 100 Mile Ultra, hosted by Phoenix Running, is a unique 100-mile trail running event held at Denbies Wine Estate in Dorking, Surrey. Designed for both seasoned ultra runners and first-timers, the race features a flat-ish, single 1-mile loop course through the scenic wine estate trails. Pa..

The Phoenix Denbies Marathon & Half Marathon, held at Denbies Wine Estate in Dorking, Surrey, offers a unique off-road trail running experience on a flat-ish 1-mile loop with slight inclines. Scheduled for June 2026, the event features flexible start times over a 30-hour window, allowing participant..

The Midsummer Munro will take place in Walton on the Hill on Sunday 21 June 2026. You can run 13 miles.

The Summer Solstice Challenge - Colchester will take place in Colchester on Sunday 21 June 2026.

Dunstable Downs Half Marathon is a scenic trail race set in the National Trust’s Dunstable Downs estate. In its sixth edition (2026), the 21.2km course with about 450m of ascent mixes ridge views, fast descents and climbs. The route begins at the National Trust Countryside Centre, visits Tree Cathed..