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 93 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
Halloween themed Backyard Ultra at Meoncross School: repeat 6.7 km out-and-back laps until one runner remains, with free parking, indoor access and medals for all.
November 2026
A coastal run on West Wittering Beach with expansive sandy flats at low tide, sea views and three distances 15.3k, 10k and 5k, chip timed with on-course water and medal.
Event Seven of the Wacky Races series is a seafront running event on 1 November 2026 at The Shack, Lee-on-the-Solent with 5K, distance-building options and a 6-hour challenge.
A 5 km run at Osborne House, Isle of Wight on 1 November 2026, on undulating woodland and parkland paths with coastal views; up to three spectators per runner receive free entry.
Nighttime trail run around Winchester on signed routes including the South Downs Way, offered in 12 km and 22 km options with mandatory headtorches.
A 7 mile chip timed trail race around The Blue Pool in Dorset on 7 November 2026. The route passes woodland, hills, heath and ridges and includes a capped canicross category; entry includes pool access for one adult and up to two children.
Trail runs near Brockenhurst in the New Forest on wide, firm gravel tracks with 21.6k, 16.7k and 10k options and on-course support.
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.
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 evening trail run from Corfe Castle with three routes across muddy heath and woodland, lit by headtorches and offering ridge views of Purbeck.
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.
A 10 miles off-road trail race in the New Forest on 22 November 2026, organised by Totton Running Club with limited entries and a Trail Running Association permit.
December 2026
Coastal 10 mile and 10K runs from Hengistbury Head along Bournemouth seafront with chip timing, water stations and a finisher medal.
Festive trail runs at Moors Valley Country Park on 6 December 2026, featuring a 2 km fun run for children and 5 km and 10 km trail races with on site parking.
A festive seafront running event in Portsmouth on 6 December 2026 with a flat course, themed medals, spot prizes, and limited entry.