Gerrards Cross
Trail Running Calendar near Gerrards Cross 2026-2027
Explore the top trail runs near Gerrards Cross for 2026-2027! We've gathered 243 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 miles through the Chilterns along canals, reservoirs and past Britain’s oldest post windmill, with trail instruction and a finisher’s medal included.
A night time closed road 10K in East London from Silverworks Island through the Royal Docks and London City Airport runway, women focused and currently sold out.
Off road cross country race of about 6 miles around Manor House Farm in Hardwick, with water crossings, limited to 300 runners and minimum age 17.
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.
A charity tower climb at 22 Bishopsgate, London covering 58 floors and over 1,500 steps with a fundraising target and included t-shirt and medal.
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.
Social 8 km trail run with North Downs views, finishing at Greyfriars Vineyard for lunch, a glass of English sparkling wine and a guided tasting.
A 7 hour time challenge along the River Thames in Staines with flexible distances, chooseable medals, on course aid and goody bags.
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 single-loop 50K trail race from Berkhamsted through The Ridgeway and Ashridge, with 800 m ascent, fully marked navigation and three on-route aid stations.
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.
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.