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 88 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
January 2027
Timed out and back event on the Itchen Way in Winchester with 2.62 mile laps, flexible starts, an aid station with hot potatoes and medals for all participants.
February 2027
Single-loop trail races of 50 miles, 50K and 20 miles around Ditcham Park School in Hampshire, following parts of the Staunton and Monarchs Ways and the South Downs Way.
Two coastal half marathons in Portsmouth and Langstone Harbour over a Valentine weekend with an optional ferry crossing and a bonus medal for completing both.
Coastal trail running around the Chidham Peninsula with AONB views, low-tide foreshore crossing and two measured distances including a 21.3k half marathon.
March 2027
Trail races through New Forest woodlands and heathland with 21.4k, 15.1k and 10k options plus chip timing and a finisher medal.
Coastal out-and-back at Milford on Sea with distances from 5K to ultra, 5.3 km laps, an aid station, medal and local facilities.
Join a themed trail run on the Meon Valley Trail with distances from 5km to Ultra Marathon and a flexible six hour time limit for all participants.
Trail races at Breamore House include 5k, 10k (11.5k) and a half marathon, plus a 5k Canicross and on-site parking.
Coastal trail run in Swanage on 13 March 2027 offering 21k, 16.5k and 10.5k routes, finishing at Corfe Castle with a vintage train return to Swanage.
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 at Stansted Park, Hampshire, offering woodland and countryside routes in three distances with chip timing, finisher medal and on-course refreshments.
Trail running in the South Downs around Winchester with 5 km, 16 km and 24 km marked, timed routes featuring outposts and free parking.
A simple trail event at Robin Hill on a single 5 km loop where runners complete as many laps as they choose, solo, in pairs or in small teams.
A Bowie inspired trail event at Hurn Forest with lap-based distances from 5K to ultra-marathon, aid stations, club facilities, and a Bowie inspired finisher medal.
A space and Beastie Boys themed trail event in Hurn Forest offering lap-based distances from 5K to ultra, themed medals, aid stations with space snacks, and a 5.3 km out-and-back lap.
April 2027
Final of the Wacky Runs series at Alexandra Sports in Portsmouth on 18 April 2027, with multiple distances, a six hour format, and a Mutley finisher medal.
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.
A multi-distance trail running event at St Giles House in April 2027 with marathon, shorter races, junior options, virtual entries, camping and charity fundraising.