Trail Running calendar near Winchelsea Beach 2026-2027

A guided trail run around Box Hill designed to gain over 1000 metres of elevation in a short distance. It features technical climbs and group pacing with a provided kit list and optional trail shoe testing.

An 80 mile December ultramarathon across Essex, Suffolk and Norfolk on December 5, 2026, with multiple checkpoints, mandatory safety kit and live tracking that includes an SOS function.

Three single-loop ultra races of 50k, 55 miles and 100 miles start and finish in Eastbourne, crossing the Seven Sisters and running toward Plumpton. Courses use grass trails, farm tracks and woodland paths on the South Downs.

A 50 km trail ultramarathon from Dorking along the Greensand Way through the Surrey Hills, with a 5 mile loop, marked and supported aid stations, electronic timing and a finisher medal.

Winter Downs 200 is a 200 mile continuous trail run that forms a loop around the South of England on established long distance trails. Runners have up to 96 hours to complete the single stage course and may use crew and three major aid stat..

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 7 hour Time Challenge in Staines along the River Thames, offering distances from 3 km up to 50 km and medals for all finishers. Signed laps, aid stations, and goody bags including a vegan option support self-paced efforts.

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 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.

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.

A dawn to dusk winter trail challenge at Box Hill, Dorking. Runners loop a roughly 10 mile trail with about 2,400 ft ascent per lap and may stop after any completed lap; entry includes insurance, medical cover, aid stations and a finisher m..

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 flexible 7 hour Time Challenge along the River Thames in Staines with distances from 3 km up to 50 km, finisher medals and goody bags. An optional Christmas Dinner at The Last Hop is available for an extra fee.

Final round of a four event winter trail series with over 95% off road on public footpaths and bridleways. Held at Trifarm in Boreham, the event uses a mostly clockwise 10 km course with on site parking and basic facilities.

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.

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.

Looped 7K and 10K courses in Chalfont St Peter and Gerrards Cross let runners choose distances from a single loop to ultramarathon. Aid stations, marked routes, crew access and medical support are provided, with prizes for top finishers in..

An annual New Year five mile cross country in Penshurst village over rolling hills and woodland trails. Open to ages 10 and above with entry fees supporting Hospice in the Weald and awards across junior, local and canicross categories.