Trail Running calendar near Heyshott 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 guided 10-mile trail run through the Chilterns along canals, reservoirs and past Britain’s oldest post windmill; includes trail technique coaching and a finisher’s medal for 2026. On-site parking and a 15 minute walk from the station.

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.

Woodland half marathon and 10k at Bedgebury National Pinetum in Kent on 18 October 2026, with traffic-free forest trails, downloadable GPX maps, medals, free photos and limited free parking.

An off‑road cross‑country race in Hardwick, Buckinghamshire, covering about 6 miles across varied terrain and water crossings. Entry is limited to 300 runners, with medals and category prizes including team awards.

A *10 km* trail run through the private grounds of Hole Park, a historic estate near Cranbrook, Kent, on 18 October 2026. Entry is priced at £25 and the event includes timed results, finisher medals and official race photography.

A trail running event on 18 October 2026 from Fernhurst Recreation Ground to the Temple of the Winds on Blackdown, featuring a 10 km route with a 866 ft climb and an approximate 4.5 km alternative. Entries online only.

Trail runs of 10 km and 5 km around Blackpit Brewery on October 18 2026, using private multi terrain trails through woodlands and estate tracks. Entrants receive a medal, a pint cup and a free drink at the finish.

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 point to point 47 miles ultra along the Thames Path and Ridgeway from Iffley to Henley-on-Thames, mostly on trails, with five aid stations, mandatory kit checks, baggage transfer and live GPS tracking.

A 30 mile out and back ultra along the River Stort and Lee navigations on the Hertfordshire Essex border, mostly flat grassy and gravel trail with checkpoints every 5 miles, electronic timing, medals for finishers and trophies for top three..

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, self-supported anti-clockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre, with a pub check at about 10 km, a four hour cut off, and a route mainly on sea wall and coastal paths.

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.

Essex Walker offers a 26 miles figure of 8 route and an 18 miles variant on footpaths and bridleways around Blackmore. It is part of the Essex and Herts Triple Challenge and includes checkpoints, refreshments, and a finishers certificate.

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.

A single-loop 50K trail race on 31 October 2026 starting and finishing in Berkhamsted. Fully marked route with three aid stations, about 800 m of ascent, a nine hour time limit and a 350 runner field.

Experience a festive 6.66 km Halloween trail run starting and finishing at a local brewery in Chelmsford. Participants enjoy a costume focused event with medals and drinks for finishers in a social atmosphere.

A night gravel trail run in Alice Holt Forest with 5 km laps and three distance options, head torch navigation, on-course outposts and on-site parking and facilities.

An evening Halloween run at Hogmoor with kids and adult loop options, varied sandy and muddy terrain, fancy dress encouraged, free parking and medals for finishers.