Isle of Wight
Walking Events Calendar near Isle of Wight 2026-2027
Monthly updates for Isle of Wight
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Isle of Wight for 2026-2027! We've gathered 11 great walks in the area. Check out our detailed list below to find your next local walk.
August 2026
Walkers can choose 2.5k, 5k, 10k, 15k laps around Bournemouth on a 2.5k loop of giant inflatable obstacles and music zones, with no timing and a midway water station.
September 2026
Walkers can take part in a free, non competitive event at Tinwood Estate in Chichester, following a route through the vineyard and surrounding countryside. The event is open to all and optional donations support cancer research.
Teams walk 100km from Queen Elizabeth Country Park along the South Downs Way over rolling chalk hills and sea views, with free camping, manned checkpoints with water, toilets and showers at the finish.
Woodland Walk from New Park Showground in Brockenhurst offers a gentle route through New Forest woodland alongside the event races. The course is not suitable for wheelchairs and cyclists and child buggies are not permitted.
November 2026
Walkers are welcome on the 15.5 mile and 21.5 mile courses from Swanmore Village Hall via the Meon Valley and South Downs Way. About 80% trail with climbs and tricky underfoot; fully stocked checkpoints, finish food and hot drinks, and walker..
January 2027
Walkers can use the rolling 21.4k or 12.1k routes from Sparsholt College across tracks, bridleways and footpaths around Farley Mount with water stations and ample parking.
Walks of 21.6k, 15.2k and 7.9k from Queen Elizabeth Country Park on hard packed trails through woodland, South Downs Way and gravel tracks with water stations.
March 2027
Walkers can choose 21k, 16.5k or 10.5k routes from Swanage seafront on firm chalk and sandy coastal trails past Old Harry Rocks and Corfe Castle, with water stations and on-course refreshments.
May 2027
Walk options 106km, 50km, 25km and Cowes 10 mile from Chale basecamp along southern coastal cliffs, with rest stops ~12.5 km, food, medics, GPS and ferry transfers.
July 2027
Walkers can choose 100 km, 75 km, 50 km, 20 km or 10 km routes from Petersfield Rugby Club across South Downs heath, woodlands and sandy tracks, with coach transport to starts and checkpoints.
Walkers can choose 2.5k, 5k, 10k or 15k, each lap a 2.5k circuit of giant inflatable obstacles in Southampton, Hampshire. The route is clearly marked with a midway water station, toilets and bag drop and there is no timing so walkers..