Highclere
Trail Running Calendar near Highclere 2026-2027
Explore the top trail runs near Highclere for 2026-2027! We've gathered 89 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
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.
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.
Experience a 9 mile trail race through the Wiltshire countryside featuring neolithic sites and muddy tracks with all profits supporting the local Air Ambulance.
Mud- and water-filled trail laps at Spider Hill with 5 km and 10 km options across marshes, swamps and steep climbs.
A timed 21k trail run across the private Farleigh Wallop Estate with cupless water stations, medics, parking included and a bespoke sustainable finisher medal.
A community silent disco run at Rose Hill Community Centre on 28 November 2026 with a group warm up, headphones for music, glow items, post-run music, raffle and on-site refreshments.
Trail running at Mapledurham Estate on 29 November 2026 with 10 km, 10 mile and half marathon routes across muddy paths, woodland and fields.
December 2026
A winter trail event on Salisbury Plain offering Marathon and Half courses, marked routes, stocked aid stations, marshal support and on-route medical cover.
A timed festive event on the Itchen Way in Winchester with flexible rock up start times, a measured out-and-back course, lap options up to ultramarathon distance, and a bespoke finisher medal.
A 10 km trail run and Canicross 10 km on December 24th around Yattendon Estate with hilly woodland trails, a medal, mince pie and a pint cup included.
Winter X is a mid winter trail running event in Hampshire's Meon Valley offering 10 km, 30 km, 50 km and 70 km routes on public trails including sections of the South Downs Way. Checkpoints, marked routes and a rock memento are provided.
Trail event at Butlers Lands Farm with water crossings, Roman Walls and fields, offering 10K and 10 Mile options plus finish line mulled wine and mince pies.
January 2027
Timed out and back event on The Itchen Way in Winchester with flexible starts, lap distances from 2.62 miles up to ultra distance, and on-course vegan options.
A winter trail run near Winchester with two off-road routes around Farley Mount, chip timing, on-course support and a finisher medal.
February 2027
A two-day, 66-mile ultramarathon along the North Downs Way with organised logistics, on-course support, and overnight accommodation.
A 30 mile non-competitive group trail run from Harting Down along parts of the South Downs Way, passing Beacon Hill, Cocking Down and Kingley Vale. Led by an experienced guide and recommended for those who have run at least 22 miles in training.