Chesham
Trail Running Calendar near Chesham 2026-2027
Explore the top trail runs near Chesham for 2026-2027! We've gathered 201 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 7 hour Time Challenge along the River Thames in Staines offering distances from 3 km up to 50 km, themed medals and distance pins, an aid table, goody bags including a vegan option, and on the day number collection.
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.
Single loop 50K trail race around the Chilterns from Berkhamsted with three aid stations, fully marked navigation and a 9 hour cutoff.
Halloween-themed Time Challenge in Staines along the River Thames with distances from 3 km up to 50 km and medals for finishers.
November 2026
Autumn trail races at Wendover Woods offering Marathon, Half Marathon, 10k and Junior Run on hilly, multi-terrain loops with on-site facilities and a six hour cut off.
Two days of marathon and half marathon races around Caldecotte Lake in Milton Keynes on 6 and 7 November 2026, with multi-lap clockwise courses, on-course water and toilets, enforced time limits, and bespoke finisher medals.
Take on flat, scenic laps along the Thames towpath in Walton on Thames with flexible starts and distances from 5 km to ultra. Limited places, aid stations, digital results and medals make this a friendly, festival style challenge.
A seven hour timed event in Staines upon Thames on 6 Nov 2026 offering distances from 5 km to ultra, a poppy finisher medal, and on-course aid with vegan options.
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.
A riverside marathon and half marathon on 8 November 2026 featuring a two minute silence pause, flat towpath laps, limited places and medals for all participants.
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 13.1 mile race along the Grand Union Canal from Cowley to Cassiobury Park with chip timing, four water stations and an optional coach transfer from the finish.
Second Sunday 5 on 8 November 2026 at Richardson Evans Memorial Fields in Wimbledon Common is an informal two lap event organised by Thames Hare & Hounds.