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.
October 2026
Forest of Bere timed event with flexible start format, a 3.28 mile lap and options from 5 km to ultra. Aid station offers sweet and savoury food including signature potatoes and vegan choices; 20% of proceeds go to 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.
Community organised 5k in Aldershot on 11 October 2026 with a flat course on the Polo Fields and Basingstoke Canal towpath, chip timing and finisher medals.
A hip hop themed coastal run at Milford on Sea offering flexible distances from 5K to ultra and 5.3 km laps, with aid stations, a cupless policy, bag drop and a themed medal.
A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.
November 2026
Coastal 15.3k, 10k and 5k runs on West Wittering Beach with chip timing, water stations, on-course marshals and a finisher medal.
Trail routes of 21.3 km, 16.5 km and 12 km from Goodwood through the South Downs with varied surfaces, canicross options and certified finishers' items.
A torchlit trail run from Winchester Athletics Track with 12 km and 22 km options across the South Downs Way and local trails. The course is fully marked; headtorches and at least 500 ml of fluid are required.
A supported endurance event on 7 November 2026 with a 76 km ultramarathon or 36 km run or walk from Aldershot or Petersfield to Portsmouth, featuring break stops, satellite tracking, medical cover and charity fundraising options.
Timed multi lap event on the Itchen Way in Winchester on 14 November 2026, with 2.62 mile laps that add up to half marathon, marathon and ultra distances. Flexible start format, aid station with vegan options, bespoke finisher's medal.
Trail runs from Roundhill Campsite near Brockenhurst through New Forest woodland and heathland, offering three distances, wildlife sightings and a finisher medal.
MoRunning at Southampton Common offers chip timed 1.5k, 5k, 10k and a half marathon with medals, finisher headbands and on-site race facilities. The course mixes paths, trails and grass and is dog friendly and buggy usable.