Trail Running calendar near Winchester 2026-2027

We have found 555 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

A timed charity run along the Thames with lap options from 5.3 km up to ultra distances. The Run for a Tenner entry donates £10 to Rays of Sunshine and all finishers receive a bespoke medal.

A mixed-terrain *10 km* organised by Emersons Green Running Club at Mangotsfield School, limited to 200 entries, with recycled-material medals and proceeds funding tree planting.

Trail running event in the South Downs National Park with 100k, 75k, 50k, 20k and 10k options from Petersfield Rugby Club; coach transport to starts and weekend camping are provided.

Vivo Life Superhuman Games is an outdoor functional fitness competition at Greville Smyth Sports Ground on 4 July 2026. Teams and pairs compete in five 20-minute AMRAP workouts that test lifting, carries, obstacles and VO2 capacity.

Choose your own challenge at the Summer Sun Run, a flexible lap event set in the scenic Denbies Wine Estate. Complete as many 5.3 km laps as you like within 7 hours, with a large medal for all finishers. Enjoy a flexible start window and a..

Race 2 of the Orion Harriers Forest Five series takes place on 04 July 2026 at Jubilee Retreat as part of a three-race series with age-category aggregate trophies and prizes for individual and team placings.

An evening trail event on 4 July 2026 based at the Fox Inn in Ansty, Dorchester with a 10k course and 220 m of elevation, venue music and food, accommodation options, finisher medals and trophies to third place male and female.

A muddy obstacle 5k at Kempton Park Racecourse on 4 July 2026 featuring climbs, crawls and slides with staggered wave starts. The event includes free on-site parking, nearby train and bus links and a minimum fundraising target.

A 21.1 km off-road half marathon along The Ridgeway between Wendover and Princes Risborough. The fully marked course has 526 m+ ascent, aid stations at Cadsden, field limit of 350 and UTMB World Series index status.

Two off road races around Bewl Water on 5 July 2026 organised by Wadhurst Runners. The 15 mile route includes the nature reserve and a four hour time limit; finishers receive a medal, t shirt and refreshments.

A women only trail event at Denbies Wine Estate on 5 July 2026 offering 50K, 25K, 10K and a kids race. Routes have GPX downloads, there are no cut offs, and both attended and virtual participants receive a memento.

Trail races of 5, 10 and 15 miles take place in Moors Valley Country Park in Dorset on 5 July 2026. The event includes chip timing, feed stations, medical support and a bespoke finisher medal.

Timed multi-lap road event on The Itchen Way in Winchester offering 2.62 mile laps, a seven hour running window, an American theme with costume trophies, and on-course aid with vegan options.

A riverside running event on Sunday 5 July 2026 offering 10 mile, 10k and children's races between Hertford and Ware, with proceeds donated to the Essex & Herts Air Ambulance and T-shirts and medals for adult finishers.

A 5k obstacle course at Fairlands Valley Park where participants aged 13 and over climb, crawl and slide through muddy challenges while fundraising for Cancer Research UK. The mixed grass and paved course includes staggered wave starts and..

A community trail run hosted by Muslim Runners in Epping Forest on July 5, 2026. Multiple pace groups and a 30 minute walking option, with bag drop and coffee afterwards at Butlers Retreat.

A 10 km group trail run across Thursley National Nature Reserve in Surrey, set on mainly flat heathland and boardwalks. Evening and night options include headtorch runs and there may be an alcohol free beer at the end.

An off‑road two-lap race through Hainault Forest organised by Ilford Athletic Club on 8 July 2026, supporting St. Francis Hospice and forming Leg 5 of the Elvis Grand Prix.

A 6-hour timed run along the flat Jubilee River in Slough on July 9, 2026. Participants complete laps of 5.24 miles, choosing their own distance. Every finisher gets a medal.

SATURN Midweek Chasing Numbers on 10 July 2026 is a 7 hour timed challenge along the River Thames with options from 3 km up to 50 km. The event includes aid stations, medals, goody bags and distance pins.

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