Maidenhead
Trail Running Calendar near Maidenhead 2026-2027
Explore the top trail runs near Maidenhead for 2026-2027! We've gathered 228 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
June 2027
A forest trail event at Wendover Woods offering a hilly multi-lap 10 km course with Half Marathon, 10k and Junior Run options, on-site facilities for spectators, route maps and GPX files, and medals plus free photos for participants.
An urban ultramarathon in central London with 100km, 50km and 25km routes that pass over 100 city landmarks, with checkpoints and training resources.
A muddy 5k obstacle course at Cassiobury Park where participants climb, crawl and slide through timed waves while raising funds for cancer research.
A 75 mile off road ultra on a one mile loop at Denbies Wine Estate with up to 30 hours to finish, chip timing and multiple concurrent race options.
A 100 mile ultra on a flat one mile trail loop at Denbies Wine Estate offering 12 hour and 24 hour options plus 50, 75 and shorter races.
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.
Run one mile on the hour for 12 consecutive hours at Denbies Wine Estate with chip timing, a finisher medal, camping and a simultaneous virtual option.
A trail running event at Cranleigh Showground on Saturday 19 June 2027 with routes from 5 km to 53 km across Surrey hills and forests. Fully marked courses, varied outposts, free parking and an event village with food and a non alcoholic beer.
Timed event at Denbies Wine Estate on 20 June 2027 using a 1 mile loop; runners choose distances from 1 mile to ultra and run laps within a six hour limit.
Scenic trail half marathon across Dunstable Downs in June 2027, 21.2 km with 450 m ascent, marked route, two aid stations and a 250 runner limit.
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.
July 2027
A 21.1 km trail race along The Ridgeway between Wendover and Princes Risborough in Buckinghamshire, fully marked with two aid stations and a 4 hour time limit.
Group guided 10 km trail run across the boardwalk and heathland of Thursley National Nature Reserve with evening and night options, car parking and a post-run alcohol-free beer.
A Ridgeway trail event on 10–11 July 2027 offering 50 km and 100 km formats, finishing at Avebury Standing Stones with marked trails, pitstops, medical support, and on course services.