Gerrards Cross
Trail Running Calendar near Gerrards Cross 2026-2027
Explore the top trail runs near Gerrards Cross for 2026-2027! We've gathered 263 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A relaxed Halloween-themed 3 km obstacle run on a new course with waves of participants, mandatory headtorch, on-course burpee penalties, and optional costumes.
A fully marked single loop 50K trail race around the Chilterns with three checkpoints, a 9 hour limit and start finish at Berkhamsted Cricket Club.
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
Trail races at Wendover Woods offer marathon, half, 10k and junior distances on hilly mixed forest trails with views from Haddington Hill.
Night orienteering on Wimbledon Common with two technical courses, race centre at The Crooked Billet and online only entry.
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 remembrance midweek run by Saturn Running in Staines upon Thames offering multiple distances and a poppy finisher medal along the River Thames.
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.
Trail event in Windsor on 8 November 2026 with chip timed 10K and half marathon from Alexandra Gardens, featuring medals, free photos and an event village.
Riverside marathon and half marathon on Remembrance Sunday 8 November 2026, built around a two minute silence at 11:00 with flat 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.
Second Sunday 5 on 8 November 2026 at Richardson Evans Memorial Fields, Putney Vale, a relaxed two lap run organised by Thames Hare & Hounds.