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.
October 2026
Forest of Bere timed event with flexible start format, a 3.28 mile lap and options from 5 km to ultra. Aid station offers sweet and savoury food including signature potatoes and vegan choices; 20% of proceeds go to 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.
A hip hop themed coastal run at Milford on Sea offering flexible distances from 5K to ultra and 5.3 km laps, with aid stations, a cupless policy, bag drop and a themed medal.
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.
A torchlit trail run from Winchester Athletics Track with 12 km and 22 km options across the South Downs Way and local trails. The course is fully marked; headtorches and at least 500 ml of fluid are required.
Timed multi lap event on the Itchen Way in Winchester on 14 November 2026, with 2.62 mile laps that add up to half marathon, marathon and ultra distances. Flexible start format, aid station with vegan options, bespoke finisher's medal.
Trail runs from Roundhill Campsite near Brockenhurst through New Forest woodland and heathland, offering three distances, wildlife sightings and a finisher medal.
MoRunning at Southampton Common offers chip timed 1.5k, 5k, 10k and a half marathon with medals, finisher headbands and on-site race facilities. The course mixes paths, trails and grass and is dog friendly and buggy usable.
An underground marathon at UCAP BUNKER near Portsmouth on 21 November 2026. The multi lapped route runs through low tunnels, has a six and a half hour cut off, and requires a headtorch and cycle helmet.
Scenic 10 mile off road trail race in the New Forest hosted by Totton Running Club with medals, water stations, parking and trophies for overall and age category winners.
December 2026
Coastal 10 Mile and 10K races from Hengistbury Head along Bournemouth seafront with chip timing and a finisher's medal.
Seasonal trail runs at Moors Valley Country Park featuring a 2 km Santa fun run for children plus 5 km and 10 km trail races, entries from £12.
A timed trail event in the Forest of Bere featuring a 3.28 mile lap and distance options from 5 km to ultra. Aid station serves sweet and savoury food including potatoes and vegan choices, and 20% of proceeds support Forestry England.
A 10 mile cross country run on the West Wight with notable hills and coastal views, organised by West Wight Sports and Community Centre on 13 December 2026. Past entrants note strong on-course support, windy conditions, a scarf memento and post-race..