Trail Running calendar near Isle of Wight 2026-2027

We have found 338 Trailruns within 80 miles of Isle of Wight. See below where and when you can find the races.

Run under the stars at Stonor Park for the Maverick Dark Oxfordshire Trail on 7 November 2026. Choose 7 km, 13 km or 17 km marked, timed routes with atmospheric night running and outposts on the longer courses.

Explore autumn trails at Stonor Park and the Chilterns on 7 November 2026 with 7 km, 13 km and 22 km routes, wildlife and scenic woodland. Fully marked, timed and a finisher medal await in this friendly trail event.

Run from Alexandra Gardens in Windsor along flat, fast off road trails through parkland and woodland. Choose 10K or half marathon with chip timing, free photos and an event village serving food and giveaways.

Join the Remembrance Run on 8 November 2026 at Wraysbury for a moving riverside event honouring those who died, with a two minute silence during the race. Choose distances from 3 km to ultras and earn a finisher medal.

Join the Remembrance Run on 8 November 2026 for a scenic timed challenge along the River Thames where you pick your distance from 3 km up to ultra. A two minute silence will be observed and finishers from 3 km receive a medal.

Run through ancient woodland and heathland in the New Forest near Brockenhurst, where free roaming ponies, horses and deer may appear. Choose the half marathon or a shorter route and enjoy a medal, finisher's gift and drink.

Tackle the Wendover Woods 50, a rugged 50 mile trail challenge across five 10 mile loops through scenic woodland with roughly 10,000 feet of climb. Expect technical forest trails, full support and a dramatic finish at Trig Point Field.

UTMB Index

Run under the stars around historic Corfe Castle this November with Maverick Race. Choose 5, 11 or 15 km routes over ridge paths, woods and muddy trails, then warm up by fire pits with hot food and a finisher medal.

Join the Thames Path Trail Run in Berkshire on Saturday 21 November 2026 for scenic riverside running from Alexandra Gardens. Choose 21 km or 16 km on flat trails and finish with a medal, drink and goodies.

Take on the Kingston 10k on 22 November 2026, a lively road race that winds through Kingston streets and along the river towpath. Enjoy chip timing, a finisher medal and goodie bag, and support Kingston Hospital Charity.

Guided 10km trail run around the dramatic Devil's Punchbowl in Hindhead, led by an experienced trail coach. Social group sessions run at dusk or night with headtorches for a fun, steady off road challenge.

Join the Sussex Downs Trail Run on 28 November 2026 from Plumpton Racecourse for scenic ridge top views across the South Downs and the sea. Pick 9 km, 12 km or 21 km trails and finish with a medal and goodies.

Take in riverside views at the Riverside Marathon and Half Marathon in Walton on Thames on 28 November 2026. Flat, UKA certified towpath course, limited places, medals for all finishers and virtual entry available.

Run a flat UKA certified riverside course along the Thames at the Riverside Marathon and Half in Walton on Thames. Choose attended or virtual entry, grab a limited spot and earn a finisher medal after laps on the scenic towpath.

Run 30 miles from Haslemere, Surrey along the Serpent Trail and Sussex Border Path in a led, social ultra. Expect hilly, scenic trails through woods, heath and downs for a rewarding challenge.

December 2026

Tackle Box Hill on a guided 12.5 mile trail run with about 1000 m of climbing through woodland, heathland and open fields. An experienced guide will lead a steady group pace for runners who can hold roughly 10 min per mile, with parking nea..

Choose 10 Mile or 10K starting at Hengistbury Head and run Bournemouth seafront via Boscombe Pier on largely flat, traffic free paths with sea views. Chip timed and marshalled, the event offers water, post race treats and a medal for finish..

Experience the dramatic Jurassic Coast around Swanage on 6 December 2025 with wet, challenging trail and coastal climbs from 10K to ultra. Fully marked course with electronic timing and finishers medals, but entries are full.

Take on the Freedom Racing Hurtwood 50k on 6 December and tackle a fully signed trail through the scenic Surrey Hills, starting from Dorking. Expect a five mile loop for lead runners, regular aid stations and live timing with a generous 10..

The Mince Pie 10 will take place in Peacehaven on Sunday 6 December 2026. You can run 10 miles.