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.
February 2027
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.
A two day 66 mile winter trail event on the North Downs Way with marked routes, staffed aid stations, overnight accommodation and luggage transfers.
Two coastal half marathons in Portsmouth and Langstone across Valentine’s weekend, with an optional ferry crossing and a bonus medal for completing both days.
BigMud Trails (EARTH) offers three single lap trail races in the Meon Valley from Queen Elizabeth Country Park. Courses include climbs to Butser Hill, stocked aid stations, mandatory fluid carry and an option to plant a tree instead of a medal.
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.
Coastal trail runs around Chidham Peninsula with views across Chichester Harbour, offering 21.3k and 16.1k routes plus chip timing and on-course refreshments.
March 2027
A coastal mixed terrain event at Milford on Sea with an out and back 5.3 km lap. Runners pick their distance from 5K to ultra with aid stations, toilets, and a medal for anyone completing at least one lap.
A 24 hour endurance format at Alice Holt Forest where runners repeat a 6.7 km loop each hour, finishing laps within 60 minutes. Wooden medals are given to finishers and a wooden trophy is awarded to the overall champion.
Point to point trail races on the South Downs Way offering a 50 mile ultra, a 50 km ultra and a marathon with marked routes, aid stations, coach transfers and an option to plant a tree instead of taking a medal.
Trail races of 21.4k, 16.1k and 10k through South Downs woodlands and estate grounds with chip timing, medals and on course support.
Trail running at Matterley Basin on 20 March 2027 with three route choices through South Downs chalk downland, woodland and ridgelines; marked courses, hydration outposts and free parking.
A David Bowie themed trail event at Hurn Forest with lap based distances from 5K to ultra and a Bowie inspired finisher medal.
A space‑themed trail event at Hurn Forest with distances from 5 km to ultra, 5.3 km laps, themed medal and aid station, and 20% of fees to Forestry England.
A two lap multi terrain 10 km trail race on Easter Monday around Mortimer Fairground and local woodlands, with a canicross option, chip timing, medal and free race photos. The undulating course is not suitable for pushchairs or wheelchairs.
April 2027
A 40 or 50 mile trail ultra along the Testway from Linkenholt to Totton in Southampton, with aid stations every 10 miles, marshals and medical support. A shuttle option is available for an extra £10 and there is a 14 hour cutoff.
A blindfolded navigation challenge in Winchester where participants are dropped at unknown locations and must find their way back on foot. Options include 6 miles for visitors and 10 or 15 miles; no maps or GPS and a sealed emergency bag is used.
May 2027
A five mile off road race through woods and farmland around Hurstbourne Tarrant in the North Wessex Downs. Organised entirely by volunteers since 2009, the annual event donates all proceeds to local charities.