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.
November 2026
A three day 84 mile ultra along the Ridgeway from Buckinghamshire to Wiltshire with overnight stays in Watlington and Didcot and full or single day entry options.
A flexible Friday running event on a flat 5.3 km out and back course along the Thames offering distances from 5 km to ultra, timed over a seven hour limit with bespoke finishers medals.
Timed multi-lap run on a flat Thames towpath in Walton on Thames with distances from 5 km to ultra, a seven hour limit, flexible one hour start window and finishers medal options.
A half-day 10 km trail run in the Chiltern Hills followed by a private Tring Brewery tour with a tasting and a beer option.
Mud- and water-filled trail laps at Spider Hill with 5 km and 10 km options across marshes, swamps and steep climbs.
A Half Marathon and a 10k on Wimbledon Common in London supporting Beder, with a trail marked course, course marshals and an event village offering food, drink and partner goodies.
A 10 km road and riverside run starting and finishing at Kingston Hawker Centre, using chip timing and offering a finisher medal, refreshments and baggage drop. The event supports Kingston Hospital Charity and notes nearby train and local parking o..
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.
Complete as many 5 km laps as possible on a marked trail loop from Peaslake Community Hall, with a 2 km ascent toward Pitch Hill and a downhill return. Solo and three-person team entries are available, with refreshments and prizes included.
A charity Friday run in Walton on Thames where the £10 entry fee is donated to Rays of Sunshine. Flexible rock up and run format on a flat 5.3 km riverside lap with a finishers' medal for all participants.
A riverside marathon and half marathon along the River Thames on an accurately measured UKA certified course. Multiple laps on a flat towpath route with medals for all finishers and virtual entries.
A timed 21k trail run across the private Farleigh Wallop Estate with cupless water stations, medics, parking included and a bespoke sustainable finisher medal.
A community silent disco run at Rose Hill Community Centre on 28 November 2026 with a group warm up, headphones for music, glow items, post-run music, raffle and on-site refreshments.
A guided 30 mile trail run from Haslemere that follows sections of the Serpent Trail and Sussex Border Path, aimed at runners attempting an ultra for the first time. Group pace, varied terrain, cost £55.
Join the Christmas Advent Run on Sunday 29 November in Walton on Thames for a festive riverside run. Tackle timed laps to suit you and enjoy optional medal and chocolate advent calendar plus a prize draw.