Trail Running calendar near Windsor 2026-2027

A lakeside Christmas event in Milton Keynes offering marathon and half marathon options with 7½ and 3½ clockwise laps of Caldecotte Lake. Finishers receive a bespoke medal and the event is held under 100 Marathon Club rules.

A 10 km trail run and canicross at Renegade Brewery on the Yattendon Estate. The course is mostly off road with one water refill station and finishers receive a medal, a pint cup with a free drink and a mince pie.

A 7 hour Time Challenge along the River Thames at Wraysbury Skiff and Punting Club offering flexible distances from 3 km up to 50 km. Finishers receive a Christmas medal, distance pins for longer races, goody bags and a festive aid table.

A traditional 3.5 mile Boxing Day run around Hindhead commons and the Devils Punch Bowl, with Mens, Ladies and a Drinking Run category. All profits support Holy Cross Hospital.

A cupless charity run through Rathfinny Wine Estate in the South Downs, presented as two 5 km loops over grass and chalky trails. Part of the entry fee supports the WOLO Foundation and parking rules aim to reduce car travel.

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.

Winter X is a mid-winter trail-running event in the Meon Valley offering 10, 30, 50 and 70 km on marked public trails with checkpoints and post-event food. Entries for 2025 are closed; a provisional date for 2026 is 28 December 2026.

A winter cross-country event at Butlers Lands Farm featuring water crossings, Roman Walls, fields and footpaths. Distances are 10K and 10 Mile with entry fees from £32 to £35; finish-line refreshments include mulled wine and mince pies.

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 cross country meeting in Penshurst on 3 January 2027 offering a 5-mile race and a 5-mile canicross option on winter trails, organised by Penshurst Cross Country Run.

A 43 mile point to point ultra from Wendover to Little Venice mixing country trails, roads and canal towpath. The event uses GPS tracking, has five checkpoints and a baggage transfer, and is open to runners aged 18 and over.

The Doughnut Dash is a flexible-distance run along a flat Thames riverside trail. Participants can run from a single lap to ultra marathon distances while enjoying doughnuts. All finishers receive a custom, neon-colored medal.

Trail runs from Sparsholt College around Farley Mount in Hampshire, offering 21.4 km and 12.1 km routes, chip timing, water stations, finisher medal, and first aid.

A road event on the Windmill Way in Bury St Edmunds on 16 January 2027 offering distances from 5k to ultra with aid stations every 10 km. Parking is included and finishers receive a bespoke or lucky dip medal.

A six hour loop event at Ryton Pools Country Park on a 3.3 mile crushed stone route around pools and pasture. Participants run as many laps as they wish within six hours; canicross and rucking are permitted and a portion of entries supports..

Trail races at Moors Valley Country Park and Forest feature a half marathon and a 10K on marked woodland routes with chip timing. The event includes aid stations, limited canicross places, event photography and several eco friendly measures..

Trail runs of 21.6 km, 15.2 km and 7.9 km around Queen Elizabeth Country Park in the South Downs, featuring tree lined trails, varied off road surfaces, chip timing and a finisher medal.

A twilight trail run in Hurn Forest with 5 or 10 mile out and back routes. Torches are required, 20% of entry fees go to Forestry England, and basic on-site facilities include an aid station and toilets.

A winter trail 10 km through medieval Lavenham along an old railway line, featuring mixed terrain, mud and shallow streams. All finishers receive a medal and podium trophies are awarded for top finishers.

Squirrel Challenge at Daventry Country Park is a six hour timed event on a 3.3 mile off-road loop where participants complete as many laps as they choose. Canicross is permitted and the route passes woods, open grassland and water.