Trail Running calendar near Ventnor 2026-2027

Join a 30 mile guided group run exploring the scenic Surrey Hills and Box Hill. This event offers professional coaching on the trails and is an ideal entry point for those new to ultra running.

Experience the worlds largest inflatable obstacle course at Kempton Park. Navigate a variety of bouncy structures in this fun event located in South London on Saturday 3rd October 2026.

Experience a scenic 50km ultra marathon from Moors Valley Country Park to the Bournemouth coastline. This flat point to point course features forest trails and seafront paths with full medical and navigation support.

Experience an ultra distance eco trail through the ancient woodlands of London. This event takes runners on a 50 km journey starting from Capel Road into the natural paths of Epping Forest.

Experience the South Downs after sunset with looped races starting at dusk. Choose from three distances featuring rolling trails and reflective course markings under an official Dark Sky Reserve.

A *50 km* point-to-point ultramarathon from Moors Valley Country Park to Hengistbury Head, featuring forest trails, coastal paths and a fully signed flat course. The race includes four feed stations, a GPS route file, medical cover and a 9...

Experience a flat and fast riverside trail race along the scenic Thames Path in Richmond. Choose from 10km, half marathon, or marathon distances on a well marshalled out and back course.

Explore the scenic Hambleden and Stonor valleys with three distance options starting from Marlow. Enjoy a managed challenge event featuring checkpoint snacks and a finish line meal in the heart of the Chilterns.

A flexible 6-hour timed run along the flat Jubilee River towpath. Run one 5.24-mile lap or see how many you can complete. The scenic route passes through countryside with views towards Windsor Castle.

Experience the iconic trails of Surrey with a choice of three distances through woodland paths and ridgelines. Enjoy a chip timed challenge featuring elevation and scenic views at Box Hill.

Test your endurance at Pippingford Park with 10 laps in 10 hours. Choose between three different loop distances on a private estate and earn your finisher shirt based on your performance in this unique timed challenge.

Choose a scenic 10k or shorter 5k through the Chiltern Hills around Frieth, combining woodland paths and country roads. Expect rolling climbs and panoramic views for a rewarding, hilly challenge for road and trail runners.

The Titsey Trail 10k is a community running event held on Sunday, 11th October 2026. Organized by runners for runners, it raises funds for a variety of local charities.

The FOOBS Trail and Fun Runs return in October. Choose from a chip timed 10K, 6K, or a family friendly 2K fun run through the countryside near Old Basing. The event supports local schools through community fundraising.

MacTuffX Swindon features a series of repetition based running formats including solo and team categories. Participants choose between multiple 400m or 800m loops in this structured athletic event for adults.

Experience the landscape of the Isle of Purbeck and the Jurassic Coast with three trail distances starting near Corfe Castle. This dog friendly event features technical coastal paths and views of historic landmarks in Dorset.

A 100 mile trail race through Oxfordshire featuring four 25 mile out and back spurs. Runners navigate the historic Ridgeway and Thames Path trails supported by 16 aid stations and full medical coverage.

Join this annual cross country challenge through the footpaths of Kent, Surrey, and Sussex. Choose between 25km and 50km distances with full checkpoint support and post event catering included.

Roughly 12K trail run on bridle paths and the Imber Range near the Westbury White Horse on 18 October 2026. Limited to 200 places so book early for a bespoke finisher medal and category prizes.

Experience a premier trail running weekend in Eastbourne featuring an ultra, marathon, half marathon, and 10k. Run along the scenic Seven Sisters with well stocked aid stations and a supportive atmosphere for all participants.