Trail Running calendar near Chesham 2026-2027

Festive trail runs at Wendover Woods on 20 December 2026, with a Family Santa Mile and 5- and 10-mile races; finishers receive medals and seasonal treats. Entry fees range from £14 to £29.

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 Christmas Eve trail 10 km at Renegade Brewery in Yattendon that includes a medal, a pint cup with a free drink and a mince pie. Canicross entry is available and the event raises funds for Newbury Riding for the Disabled and PALS.

A seven hour Time Challenge along the River Thames in Egham with flexible distances from 3 km to 50 km, signed laps, medals, distance pins and goody bags, plus a Christmas dinner aid table and a small present for finishers.

The Boxing Day Run - Hindhead will take place in Hindhead on Saturday 26 December 2026. You can run 4 miles.

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.

A lapped multi terrain event at Brandon Country Park featuring a 5.3 km circuit and flexible four or six hour options. Aid stations are provided each lap, parking is chargeable and the event is cupless.

Multi-distance road event from Suffolk Running Centre near Bury St Edmunds offering 5k, 10k, half, marathon and ultra options. The Windmill Way and Golding Hills course has rolling hills, aid stations every 10 km and bespoke finisher medals..

A six hour lap event at Ryton Pools Country Park near Coventry where runners, walkers and canicross participants complete as many 3.3 mile loops as they can. A share of entry fees supports Roald Dahl's Marvellous Children's Charity.

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.

Trail runs start and finish in Queen Elizabeth Country Park on the South Downs, passing through Head Down, the South Downs Way and the Milky Way. Three route lengths are offered and finishers receive a medal, a drink and event goodies.

A winter trail run through medieval Lavenham along the old disused railway, covering a 10 km mixed terrain route with footpaths, forest trails and shallow streams. Manual timing, medals for all finishers and podium trophies for top places.