Trail Running calendar near Ventnor 2026-2027

An annual 25 km or 50 km challenge across Kent, Surrey and Sussex footpaths, navigated from written route directions with checkpoints, food included and a ten hour completion objective.

A roughly 12K off-road race on 18 October 2026 that follows bridle paths along the Imber Range and passes close to the Westbury White Horse, with limited places, age and equipment restrictions, and finishing medals for all.

The Blackdown Hill Challenge on 18 October 2026 is a trail running event from Fernhurst Recreation Ground to the Temple of the Winds, featuring a 866 ft climb and wide views. A shorter adult trail of about 4.5 km is also offered.

Beachy Head Marathon Weekend runs multiple trail distances from a 10k to an ultra near Bede's Prep School in BN20 7XL on 24/10/2026. Runners comment on clear signage, friendly marshals, stocked aid stations and hilly coastal terrain.

A hip-hop themed coastal run at Milford on Sea with mixed terrain and coastal views. Runners choose distances from 5 km to ultra-marathon, completing 5.3 km out and back laps with an aid station and themed medal.

Looped races at Chalfont Park and Chalfont St Peter let runners choose distances from a 7K loop to multi lap ultras. Aid station, clear course marking, crew support and medical cover are provided.

A five mile night trail run at The Plough and Harrow in Litlington on 30 October 2026, self navigated via GPX with a tail runner, timed results, Halloween fancy dress prizes and an age limit of 18 plus.

Night trail laps in Alice Holt Forest by head torch with 5 km loops. Choose 5 km, 10 km or 15 km while using one outpost per lap for snacks and hydration.

An evening Halloween trail at Hogmoor with kids and adult loops: 3.3K, 6.6K (including canicross) and 10K. The sandy, muddy course features oversized statues, on-site playground, free parking and medals for finishers.

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.

A coastal beach run at West Wittering with 15.3k, 10k and 5k options along Blue Flag sands, chip timing, water stations and a finisher medal, plus course signage and first aid cover.

An off road ultramarathon from Maiden Newton of about 35.9 miles with roughly 1,300 m of ascent, passing hillforts and coastal views. Six aid stations offer water and cake, GPX files and maps are provided for navigation.

Take on flat, scenic laps along the Thames towpath in Walton on Thames with flexible starts and distances from 5 km to ultra. Limited places, aid stations, digital results and medals make this a friendly, festival style challenge.

Trail races from Goodwood Racecourse into the South Downs National Park offering 12k, 16.5k and 21.3k distances with mixed forest roads, bridleways and single-track trails. Canicross options available and entries include chip timing and a f..

A night trail run at Stonor Park in the Chiltern Hills offering three routes of about 17 km, 12–13 km and 7 km. Courses are fully marked and timed, with outposts on the middle and long routes and a cup-free policy at feeds.

A twilight off road 10k around Eastbury Park and Chettle with wooded sections and historic landmarks. Medals, trophies and refreshments included and entries are limited to 200.

Trail runs from Stonor Park through the Chilterns with three marked routes (7 km, 13 km, 22 km), notable wildlife, steep sections and fuel outposts; facilities include free parking, timing and a finisher medal.

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.

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.

A supported endurance event on 7 November 2026 with a 76 km ultramarathon or 36 km run or walk from Aldershot or Petersfield to Portsmouth, featuring break stops, satellite tracking, medical cover and charity fundraising options.