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.
May 2027
A 10 km trail run from Marlow Rugby Club with local trails, woodland and Thames towpath, finishing with a medal, a pint cup and a free drink.
June 2027
A 24 hour relay at Wasing Park, Reading where Solos, Pairs and Teams run an undulating 8 km trail lap with camping and an on-site event village.
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.
Two supported trail runs in London: a 55 km ultra and a 25 km route on the Capital Ring with signed routes, feed stations, chip timing and finish refreshments.
Trail running at Wendover Woods on 6 June 2027 with Half Marathon, 10k, a new 5k and a junior run on hilly forest trails and on-site facilities.
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.
Scenic June 2027 trail races near Kingsclere offering marathon, half marathon and 10K on clearly marked single-lap courses with aid stations and finish-line amenities.
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.