Maidenhead
Trail Running Calendar near Maidenhead 2026-2027
Explore the top trail runs near Maidenhead for 2026-2027! We've gathered 266 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail races around Box Hill in the Surrey Hills offering three distances, steep climbs, aid stations and chip timing from a base at Box Hill National Trust.
A guided trail half marathon of about 13 miles in the Chiltern Hills with grouped pacing, a midway refreshment point and a finisher’s medal.
Off road races of 15 km and 21 km through Hurtwood Forest near Guildford, with day of registration, free parking and water stations on course.
A non-competitive, all-surface 25 km loop from Leyton with run leaders, a halfway energy stop, kit demos and community-focused proceeds for Hackney Foodbank.
Community-supported trail runs at Old Basing offering 10K and 6K chip timed races plus a 2K fun run to raise funds for local schools.
A scenic approximately 15 km trail race in Tring on 11 October 2026, running through Ashridge Estate and the Ridgeway with marshals, water stations and post-race facilities.
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 monthly five mile run in Wimbledon organised by Thames H&H running club, held on the second Sunday of each month with online entries and published results.
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.
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.