Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester for 2026-2027! We've gathered 104 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 50 km point to point multi terrain ultra linking Ramsbury and Renegade breweries, with chip timing, live tracking 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 running event in Newbury where entrants complete as many 3.5 km loops as they like to earn a medal and support New Life Special Care Babies.
A team endurance event across the South Downs covering 100 km in under 30 hours, with teams of four or a relay option and support crews meeting at checkpoints.
Trail marathon and half marathon through the Surrey Hills on 13 September 2026, based at Myrtle's Courtyard Seale, with on site parking and proceeds to local charities.
Trail running at Hambledon Vineyard with races from 1 km to 20 km, vineyard facilities, chip timing and charity fundraising.
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.
Trail races at Amport Cricket Club with 5k, 10k, 10 mile and canicross on marked multi-terrain routes, cupless stations, first aid and finish-line refreshments.
October 2026
Timed trail event in the Forest of Bere using a 3.28 mile out and back lap with distances from 5 km to ultra. Aid station offers sweet and savoury food including potatoes and vegan options; 20% of proceeds support Forestry England.
Half marathon and 10 km races at RAF Greenham Common in Thatcham, Berkshire. The traffic free, flat course has water stations, free parking and a children's race paid on the day for £5; proceeds support New Life Special Care Babies.
Trail and fun runs near Old Basing on 11 October 2026 with chip-timed 10K and 6K races plus a 2K family fun run supporting local schools.