Maidenhead
Trail Running Calendar near Maidenhead 2026-2027
Explore the top trail runs near Maidenhead for 2026-2027! We've gathered 228 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
A low key multi-lap half and full marathon along the River Thames in Walton on Thames on 28 December 2026. The UKA certified flat towpath course awards medals to all finishers and has limited places.
Trail event at Butlers Lands Farm with water crossings, Roman Walls and fields, offering 10K and 10 Mile options plus finish line mulled wine and mince pies.
January 2027
A 10.000 km trail race around Box Hill with steep climbs and scenic views, registration and parking at Denbies Vineyard. The event includes a kids fun run and a ladies race and uses a B Course around Denbies if Box Hill is unavailable.
A guided 10 km trail run in the Chilterns from Church Farm Cafe, Aldbury, featuring hills, woodland routes, on site parking and bag drop.
A long running mixed trail and road race at Epsom Racecourse offering ten mile and 10k options, timed results, wooden finisher medals and local charity fundraising.
A riverside 3.28 miles out-and-back event at Wraysbury offering distances from 5K to ultra and a six hour challenge, licensed by TRA and run under UKA rules.
Friday timed runs on a flat riverside 5.3 km lap with flexible entry options, charity allocation for the £10 run and commemorative finishers' medals.
Lap the Thames towpath in Walton-on-Thames with distances from a 5.3 km lap up to ultra plus flexible starts and medal or no medal entry options.
A 43-mile ultra from Wendover to Little Venice mixing trails, roads and canal towpath with GPS tracking, checkpoints, mandatory kit and an 11-hour cutoff.
A guided 30 mile trail run from St Martha's Hill exploring the Surrey Hills and Box Hill with an experienced ultra runner and coach. Group pace, recommended 22 miles training, cost £55 and an alcohol free beer may be available.
A flexible 7 hour time challenge along the River Thames in Staines offering distances from 3 km up to 50 km, medals, distance pins and on-course aid.
Scenic winter trail run in Windsor offering 10K and half marathon distances, with chip timing and proceeds supporting Brain Research UK.
February 2027
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.