Trail Running calendar near Woking 2026-2027

A cupless charity run across vineyard trails at Rathfinny Wine Estate, featuring two 5 km loops, limited to 75 local runners; part of each entry fee supports the WOLO Foundation and basic facilities are provided at Race HQ.

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 year-end cross-country event at Butlers Lands Farm featuring water crossings, Roman walls, fields and footpaths. Two routes are offered and entry includes a medal, engraved iTAB, free photos and chip timing.

Winter Runderland in Walton on Thames is a timed lap event on a 5.3 km riverside towpath course. Runners may select distances from 5 km up to ultra, and a lower-cost no-medal entry option is available.

A New Year trail race at Box Hill with an exact 10.000 km route, 473 m of ascent and rough tracks offering steep sections and wide views. Registration and parking are at Denbies Vineyard and headphones are not permitted.

Experience a winter trail adventure at the Penshurst Village Cross Country Run. Participants can choose between a standard five mile cross country course or a five mile cani cross run through scenic local landscapes.

A 43 mile point to point ultra from Wendover to Little Venice in London combining trails, roads and canal towpath. The event includes real time GPS tracking, checkpoints, finishers medals and prizes for top finishers.

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.

Winchester Trail Run in January 2027 offers two off road routes around Farley Mount near Winchester, including a half marathon and an Epic course with a short climb and countryside views.

The Benfleet 15 will take place in Hadleigh, Benfleet on Sunday 17 January 2027. You can run 15 miles.

A trail half marathon and 10K in Moors Valley Country Park, Dorset, run on gravel woodland paths with lap-based routes and limited canicross places. The event is chip timed, fully marked and follows several eco-friendly measures.

A twilight out and back trail in Hurn Forest offering 5 mile and 10 mile options. The event uses 2.5 mile laps, provides aid at the start and finish, and donates 20% of entry fees to Forestry England.

The Ashdown Forest 10 Mile will take place in Wych Cross on Sunday 31 January 2027. You can run between 5 and 10 miles.

An evening running event at Westonbirt Arboretum on 6 February 2027, with 5 km and 10 km routes that pass through collections of over 2,500 trees. The surface is solid underfoot and ticket sales are currently sold out.

A single-loop 53 mile trail race starting and finishing at Ditcham Park School in Petersfield. The route has about 6400 ft of ascent, six aid stations, full way marking and is worth 3 ITRA points.

Follow in the footsteps of ancient pilgrims on this 66 mile two day ultra adventure along the historic North Downs Way. Experience a supported winter trail challenge with overnight accommodation and full logistics included.

A winter running event through Westonbirt Arboretum's tree collections offering 5 km and 10 km wave entries on Sunday 7 February 2027. The organiser is Relish The Great Outdoors and tickets are currently sold out.

Join this 5 km canicross adventure through the scenic woodland tracks of Irchester Country Park. This dog-friendly event features a staggered start, professional support, and finishers medals for both runners and their canine partners.

The Bedgebury Forest 10 and 5 Mile will take place in Goudhurst on Sunday 7 February 2027. You can run between 5 and 10 miles.

A 28.2 trail marathon along the River Adur in February, starting at Shoreham Sea Scout Hut, with muddy paths and fully stocked aid stations. Prior trail marathon experience, suitable clothing and a mobile phone are required.