Gerrards Cross
Trail Running Calendar near Gerrards Cross 2026-2027
Explore the top trail runs near Gerrards Cross for 2026-2027! We've gathered 211 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail half marathon in the Chiltern Hills covering 13 miles with 300 m ascent, led groups, a midway refreshment point and a finisher’s medal.
Trail running in Hurtwood Forest near Guildford with 15 km and 21 km routes, on-site facilities, water stations and medals for all.
An all-surface 25 km loop from Leyton with run leaders, a midway energy stop and post-run kit and community space at Portal HQ.
A scenic approximate 15 km trail race around Tring and the Ashridge Estate with marshals, water stations, team prizes and a finisher snood.
A lap-based out and back run along the Thames in Walton on Thames offering distances from a single 5.3 km lap up to ultra distances with a seven hour limit.
A lap based Friday timed run on a flat 5.3 km out and back course along the river Thames, with distances from 5 km up to ultra. Both attended and virtual entrants receive a finisher medal.
A guided 10 mile trail through Chilterns waterways and reservoirs, passing Britain’s oldest post windmill, with trail instruction and a 2026 finisher’s medal.
An off road cross country race of about 6 miles across Manor House Farm in Hardwick village with varied terrain and water crossings. Entries are limited to 300 runners and a minimum age of 17 applies.
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 relaxed night obstacle run at OPP over two 1.5 km laps, with technical obstacles, surprise elements and a strict headtorch requirement.
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.