Windsor
Trail Running Calendar near Windsor 2026-2027
Explore the top trail runs near Windsor for 2026-2027! We've gathered 261 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
April 2027
Trail 10 km and a two-lap half marathon from Dummer Down Farm with brewery finish, medal, pint cup and a free drink; canicross and camping options available.
A family-friendly inflatable obstacle course in St Albans on 24 April 2027 with multiple lap distances, music zones, and on-course hydration.
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 guided 30 mile trail run from Newlands Corner along the Greensand Way with coaching, varied single track and climbs including Leith Hill, plus an alcohol free beer at the end.
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.
Two-day self-supported navigation challenge in the Surrey Hills for teams of two, with camping at Newlands Corner and a points-based course across both days.
Inflatable obstacle course in Guildford on 8 May 2027 offering 2.5K, 5K, 10K and 15K routes with music zones, inflatables and a finisher's medal.
A one-day 30 km trail run in the Chiltern Hills from Tring with guided technique instruction, checkpoint support, bag storage and a finisher's medal.
Two days of obstacle racing in Henley-on-Thames with Sprint 5 km, Super 10 km, Beast 21 km and kids races along the riverside.
A weekend running festival in Hackney featuring a 21.1 km half, night 10 km, community and trail 5 km races, schools events and a free two day 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.