Trail Running Calendar South East (England) 2026-2027

A Star Wars 50th Anniversary weekend on 5 and 6 June 2027 at Caldecotte, Milton Keynes featuring marathon and half marathon races around Caldecotte Lake, unique finisher medals, on-course water and toilets, and time limits for each race.

A 5k obstacle course at Royal Windsor Racecourse with mud obstacles to climb, crawl and slide, mixed tarmac and grass surfaces, staggered wave starts and a minimum age of 13. Earlybird entry prices and a fundraising target apply.

A 5 km obstacle course at Prospect Park in Reading where participants climb, crawl and slide across grassy slopes and woodland. Waves run every 15 minutes and the event is open to people aged 13 and over.

A 5k muddy obstacle course at Willen Lake with staggered wave starts, on-site toilets and parking, blue badge parking nearby, and a fundraising target of £50. The event is not wheelchair accessible.

Backyard Ultra at Chilton Manor Farm on 5 June 2027 features a 6706 m loop run each hour until one runner remains, with weekend camping, on route water stations, event camp facilities and medical support.

A point to point 50 km trail ultramarathon from Rochester to Tonbridge along the River Medway. The predominantly flat, fully marked course features four stocked aid stations, chip timing, live GPS tracking and an athletics track finish.

A *30 km* point-to-point trail along the River Medway from Little Fant Farm to Tonbridge, fully marked and chip-timed with three staffed checkpoints and an athletics track finish. The event has mandatory checkpoint cut-offs and an eight-hou..

At Prospect Park in Reading this Race for Life event offers a 10k run as two laps of the 5k course plus a separate 5k option, with grass and woodland terrain and some steep slopes.

Park-based 3k and 5k runs at Dunorlan Park with mixed grass and woodland terrain. The event is organised by Cancer Research UK and includes a fundraising pack and a finishers medal.

A 100 mile nonstop race along the South Downs Way from Matterley Bowl near Winchester to Eastbourne, with 12 aid stations, medical support and a 30 hour cut off.

A non-stop 50 km trail ultra along the South Downs Way with about 1150 m climb, four aid stations, full medical cover and a nine hour cut off.

Trail ultramarathon on 19th June 2027 at West Dean Gardens with 30k, 50k, 80k and 100k route options across the South Downs and coast.

A muddy 5k obstacle course around The Common in Southampton where participants climb, crawl and slide through obstacles while raising funds for cancer research. Waves run every 15 minutes and participants must be 13 or older.

A point to point 50 mile ultra and a marathon along the Three Shires Way through Bucks, Beds and Northants, finishing with a Grafham Water loop. Licensed trail races with aid stations, electronic tracking and mandatory kit requirements.

A 24 hour running festival in Milton Keynes where individuals or teams complete as many 6.55 mile laps as they wish, with camping, showers and on-site food and facilities.

Hydra 75 Mile Ultra is a 75 mile off road loop race at Denbies Wine Estate offering a single 1 mile lap, chip timing, and up to 30 hours to finish. Multiple distances and timed events take place on the same course.

A 100 mile off-road ultra at Denbies Wine Estate on 19 June 2027 using a flat one mile loop, full chip timing and multiple race options including 50 and 75 miles plus timed events.

A timed off-road Marathon and Half Marathon at Denbies Wine Estate near Dorking on a flat 1 mile loop with a flexible start window, up to 30 hours to finish, chip timing and a physical memento for all entrants.

A 24 hour attended challenge at Denbies Wine Estate in Dorking where runners complete 1 mile on the hour for 24 consecutive hours; onsite tent camping, daytime cafe service and a simultaneous virtual option are provided.

A 50 mile off-road ultra at Denbies Wine Estate on 19 June 2027 featuring a flat-ish one mile loop, chip timing and up to 30 hours to finish. Multiple timed and multi-distance options run alongside marathons and half marathons.