Trail Running calendar near Windsor 2026-2027

A 10 mile canicross loop at Grafham Water on 6 December 2026, following reservoir paths, woodland and the dam wall. Dog friendly with required harnesses, aid station water bowls and finishers medals plus a dog charm.

Bauble Bimble at Ferry Meadows is a four or six hour multi‑terrain event on a 5.3 km lap, letting runners cover distances from 5k to ultras with an aid station each lap and an event medal.

A festive 5 km off road Santa Dash at Tinkley Gate raising funds for Allsorts. Costumes, dogs on short leads and a 2.5 km one lap option for younger participants make this a family friendly event.

A festive trail running event at Moors Valley Country Park on 6 December 2026, offering a 2 km fun run for children plus 5 km and 10 km trail races; on-site parking is available for £5 and entry fees range from £12 to £26.

A 10 km trail championship at Wendover Woods on 6 December 2026 with entry by invitation for top 20 percent finishers at Runaway Racing events, age category winners and volunteers. The course is marked and timed, with awards and support fac..

A continuous 200 mile trail loop around the South of England starting and finishing at Juniper Hall, Dorking. Runners have up to 96 hours, live tracking, crew access and three major aid stations with food and sleeping facilities.

Join the Christmas Jumper Friday Run on 11 December in Walton on Thames for a relaxed rock up and run along the riverside towpath. Pick 5k to ultra, run laps within a 7 hour window and earn a bespoke finisher medal.

A festive midweek 7 hour Time Challenge along the River Thames at Wraysbury Skiff and Punting Club. Distances range from 3km up to 50km with medals, distance pins and a post-run goody bag including a vegan option.

A 100 mile winter point to point trail across the South Downs and North Downs from Amberley Museum to Juniper Hall with a 35 hour limit, three aid stations, crew and drop bag support, medical cover and a strict mandatory kit list.

A timed trail event in the Forest of Bere featuring a 3.28 mile lap and distance options from 5 km to ultra. Aid station serves sweet and savoury food including potatoes and vegan choices, and 20% of proceeds support Forestry England.

A lap based off road event at Shalford Park offering distances from 3.14 to 31.4 miles plus a one mile fun run for children. Junior lap limits, car parking and course warnings are provided by the organisers.

Seasonal trail races through Salcey Forest on 13 December 2026 offer 10k, 5k and a 1.2 km junior run. The event uses mostly flat forest trails, awards bespoke medals and prizes, welcomes seasonal fancy dress and raises funds for Shelter.

A 10 mile cross country run on the West Wight with notable hills and coastal views, organised by West Wight Sports and Community Centre on 13 December 2026. Past entrants note strong on-course support, windy conditions, a scarf memento and..

A pre Christmas anniversary timed run in Stroud on 13 December 2026 with flexible lap-based entry on a 3.28 mile canal route; distances range from 5 km to ultra and all finishers receive a bespoke medal and a memento.

Join a festive Christmas run along the flat Jubilee River. Choose your own distance in this 6-hour timed event on a scenic towpath. All finishers receive a bespoke festive medal.

A festive multi terrain cross country in Pett, East Sussex with a main five mile loop, a 2 Mile Fun Run and a children's Drumsticks Scurry. The event raises funds for Shelter and includes a bespoke medal and free photos.

Christmas Canter at Suffolk Running Centre offers 5k, 10k, half, full and ultra distances, a bespoke finisher medal, aid stations every 10k and parking included. The event uses loop and out and back formats and has a seven hour cut off.

A dawn to dusk winter trail challenge at Box Hill where runners repeat a roughly 10 mile loop with 2,400 ft elevation per lap and may stop after any completed lap; entry includes insurance, medical cover, aid stations and a finisher medal.

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.