Trail Running calendar near Maidstone 2026-2027

A 50 km trail ultra along the North Downs Way from Detling to Wye with about 1,000 m of ascent, three checkpoints and mandatory kit requirements. The route passes Boxley Warren, Thurnham Castle, Lenham Cross and the Wye Downs.

A festive trail running day at Wendover Woods on 20 December 2026 offering a Family Santa Mile plus 5 mile and 10 mile options, with medals and seasonal treats for finishers.

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.

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.

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 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.

A winter single loop trail ultramarathon in Hampshire covering about 53 miles and 6400 ft of ascent, mostly on the South Downs Way and linked trails. Entry requires a marathon qualifier and winter darkness trail running experience.

A two day, 66 mile trail ultra along the North Downs Way near Farnham, Surrey on 6 and 7 February 2027. Options include a full package with accommodation and meals or single day entries, with checkpoints and course support provided.

A point to point ultramarathon of about 48 miles along the Peddars Way from Knettishall Heath to the Norfolk coast, with GPS tracking, mandatory winter kit, three checkpoints and a shuttle bus option, plus a bespoke wooden medal at the fini..