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.
April 2027
An untimed inflatable obstacle event in St Albans on a 2.5 km lap with distances from 2.5K to 15K, medals, music zones, and on-site facilities.
An alternative to the London Marathon at Walton on Thames featuring a UKA certified 3.28 mile lap. Options include full and half marathon or a seven hour timed event, with a 150 mm finish medal for participants.
May 2027
A 100 miles point to point trail race from Richmond to Oxford along the Thames Path with marked route, at least twelve aid stations and a 30 hour cut off.
Guided 30 mile trail run near Guildford on 1 May 2027 following the North Downs Way and Greensand Way, including climbs such as Leith Hill.
Rapid Relays at Culden Faw Estate on 2 May 2027 offers 4 km loop relay racing for solo runners, pairs and teams amid woodland and Chilterns views.
A guided 12.5 mile trail run around Box Hill that gains about 1000 metres of elevation across woodland, heathland and open fields. Group pace with technical climbs and scrambling and a chance of an alcohol free beer at the finish.
A two day self supported navigation challenge for teams of two through the Surrey Hills with basic farm camping and virtual controls.
An inflatable obstacle course event in Guildford on 8 May 2027 offering 2.5k to 15k lap distances, music zones, finisher medals and family friendly entries.
A guided 30 km trail run through the Chiltern Hills with technique instruction, checkpoints, refreshments and a finisher's medal near Tring Station.
Two days of Spartan obstacle racing at Culden Faw, Henley-on-Thames, featuring Sprint, Super, Beast and Kids races along a riverside course.
Experience London's energetic Hackney Moves Festival featuring a half marathon on closed roads, a sunset 10K, and a community festival at Hackney Marshes.
A weekend of waymarked trail runs and walks at Mapledurham House near Reading, featuring ultras, a half marathon and supported marathon-length walks.
A 50 km multi terrain ultra in Maidenhead along the Thames Path, Jubilee River and Green Way with chip timing, four aid stations, live tracking and a cut off of 8 hours 57 minutes.
A 5 km obstacle event at War Memorial Park on 23 May 2027 where participants climb, crawl and slide across mixed grass and path terrain; entrants must be 13 or older and a minimum fundraising target of £50 applies.
A guided trail half marathon around the Surrey Hills, about 13 miles from St Martha's Hill in Guildford, following parts of the North Downs Way and notable viewpoints. The run is social in format with a guided pace and evening options.
A supported trail challenge from Richmond to Brighton offering distances from 10 km to 100 km with rest stops, GPS tracking, camping, and on route medical support.