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.
October 2026
Conquer 58 floors and over 1,500 steps at 22 Bishopsgate to support RNLI lifeboats while enjoying panoramic views of the London skyline.
Looped events where runners choose how many laps to run on the day, with maps, aid stations every lap and distances from 5K to 50K across several venues.
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.
A single loop 50K trail across the Chilterns from Berkhamsted with 800 m ascent, three staffed checkpoints and a 9 hour cutoff on 31 October 2026.
November 2026
Trail races in Wendover Woods on hilly, multi terrain forest loops with marathon, half marathon, 10 km and a junior run plus on site amenities and parking.
A timed remembrance run in Walton on Thames offering lap options from a single 5.3 km circuit up to ultra distances along a flat riverside course.
Experience a scenic trail run through the Bedfordshire countryside with a choice of a half marathon or metric half marathon along the Grand Union Canal and woodland paths.
A trail event in Windsor on 8 November 2026 offering a 10K and a half marathon on flat off road trails from Alexandra Gardens. The event features chip timing, race photos, post race goodies and an event village.
Remembrance Day Marathon and Half Marathon on 8 November 2026 in Walton on Thames features a race freeze two minute silence and flat riverside out and back laps.
Join a community of runners at Richmond Park for a series of timed races supporting Movember. Enjoy a hilly tarmac course with distances ranging from a kids mini run to a half marathon in a supportive atmosphere.
A point to point trail half marathon along the Grand Union Canal from Cowley to Watford with chip timing, four water stations and a wooden finisher medal.