Isle of Wight
Trail Running Calendar near Isle of Wight 2026-2027
Explore the top trail runs near Isle of Wight for 2026-2027! We've gathered 72 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
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.
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.
January 2027
Trail run near Winchester on 10 January 2027 with 21.4k and 12.1k routes around Farley Mount, chip timing and finishers medals.
A twilight trail run in Hurn Forest offering 5 or 10 mile out-and-back laps, head torches required, trail shoes recommended, and 20% of entry fees donated to Forestry England.
February 2027
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
Trail races at Hinton Admiral Estate in the New Forest offering 21.4k, 15.1k and 10k routes with chip timing, on-course refreshments and finisher medals.
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 coastal trail run from Swanage seafront to Corfe Castle with 21k, 16.5k and 10.5k options plus a vintage train return.
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.