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 73 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 30 mile ultra run from Studland Bay around the Isle of Purbeck with about 4600 ft elevation. The guided coastal route uses the Purbeck Way and South West Coast Path and passes Corfe Castle, Kimmeridge Bay, Swanage and Old Harry Rocks.
A team endurance event across the South Downs covering 100 km in under 30 hours, with teams of four or a relay option and support crews meeting at checkpoints.
Three fell races around Ventnor on the Isle of Wight offer routes from 3.8 km to 21 km with notable ascent. The series follows FRA rules, has entry limits and also serves as the SEAA Fell Running Championships.
Start the IOW Fell Running Series with St Boniface Fell in Ventnor on Sat 12 Sep 2026, a punchy 3.9 km race with 235 m of climbing across scenic Isle of Wight terrain. Pre entry or on the day entries welcome.
Tackle the Wroxall Round on 13 September 2026, a scenic 21.1 km fell run around Ventnor with about 487 m of ascent. Open to adults, with on the day entries and team places, this is race 3 of the Isle of Wight Fell Running Series.
Trail running at Hambledon Vineyard with races from 1 km to 20 km, vineyard facilities, chip timing and charity fundraising.
BigSky is the "Air" event in the Classic Element Trail Series on 20 September 2026 at Hyde Common, New Forest. Routes of 18 miles, marathon and 50k run over marked trails with multiple aid stations, mandatory fluid carriage and a bespoke finishers me..
A technical looped forest trail at Avon Tyrrell in the New Forest with choices from 5K to ultra, on-course aid, facilities and a finisher medal.
October 2026
A point to point 50 km ultramarathon from Moors Valley Country Park to Hengistbury Head, following forest trails, the Castleman Trailway and the Bournemouth seafront, with feed stations, GPS route files and a bespoke finisher medal.
Timed trail event in the Forest of Bere using a 3.28 mile out and back lap with distances from 5 km to ultra. Aid station offers sweet and savoury food including potatoes and vegan options; 20% of proceeds support Forestry England.
A seaside 12 km race in Studland Bay, Dorset, starting and finishing at the National Trust visitors centre. Prizes for the top three men and women and a race memento for all participants.
Coastal out and back run at Milford on Sea with a hip hop theme, flexible starts and distance choices from 5K to ultra marathon.
A timed, lap-based run along the Itchen Way in Winchester with 2.62 mile loops, a seven hour limit, flexible start times, an aid station with vegan options, and a bespoke finisher's medal.
November 2026
Coastal 15.3k, 10k and 5k runs on West Wittering Beach with chip timing, water stations, on-course marshals and a finisher medal.
Trail routes of 21.3 km, 16.5 km and 12 km from Goodwood through the South Downs with varied surfaces, canicross options and certified finishers' items.