Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester for 2026-2027! We've gathered 99 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 103 mile trail run along the North Downs Way from Farnham to Ashford, featuring 11,000 ft of ascent, 12 aid stations and a 30 hour finish cut off.
Trail races in Bordon with wet, sandy and technical single track; choose a 5 km single lap or a 10 km double lap with a 75 minute first lap cut off.
This timed event on August 15, 2026, offers a flexible, multi-lap format on a smooth riverside course in Winchester. Runners can choose their start time and distance, from a single lap to an ultra marathon, within a 7-hour window. All finishers recei..
Point-to-point mixed terrain running from Mayflower Park following the Old Way pilgrim trail, with 15 Mile and Marathon options. The route includes a short boat crossing of the Hamble River and passes several historic landmarks.
September 2026
Point to point 50 km ultramarathon linking Ramsbury Brewery and Renegade Brewery with mostly off-road terrain, four aid stations and a nine hour cut off.
Trail marathon and half marathon in North Hampshire on 05/09/2026, with climbs to 280 m, scenic countryside routes, marked courses, aid stations and chip timing. A Military Cup allows serving units to compete as teams.
A 12-hour looped run at Bloor Homes Southern Regional Office in Newbury where participants complete 3.5 km loops to earn a bespoke medal, with prizes for most loops. The event supports New Life Special Care Babies, is limited to 100 entrants and is 1..
Community led 10 km trail at Dummer Down Farm with chip timing, post run food and brewery drinks, a race village and a donation to Mind.
A 100 km team endurance trek across the South Downs in September 2026, combining checkpoints, support crews and fundraising for The Gurkha Welfare Trust.
A trail running event on 13th September 2026 in Seale, based at Myrtle’s Courtyard, with marathon and half marathon routes along the Pilgrims Way and North Downs Way that raise funds for local charities.
A scenic trail running event at Hambledon Vineyard offering races from 1 km to 20 km, chip timed with trophies and fundraising for Brain Tumour Research and Hambledon Primary School.
BigSky is the "Air" event in the Classic Element Trail Series on 20 September 2026 at Hyde Common, New Forest. Routes of 18 miles, marathon and 50k run over marked trails with multiple aid stations, mandatory fluid carriage and a bespoke finishers me..
A technical looped forest trail at Avon Tyrrell in the New Forest with choices from 5K to ultra, on-course aid, facilities and a finisher medal.
Trail races at Salisbury Racecourse offer marathon, half marathon and 10 km over undulating downland with woodland and Martin Down turf. GPX routes are provided and finishers receive a medal; top three men and women earn trophies.
Multi terrain trail event in Amport with 5 km, 10 km, 10 mile and canicross options, age rules, marked routes and cupless hydration.