Trail Running calendar near Medstead 2026-2027

Looped trail event near Maidstone through the Kent Downs with 50 km, 25 km and 10 km options. The route is fully signed and supported with covered rest stops, medical teams, GPS tracking and weekend camping at basecamp.

A backyard ultra at Turvey House where runners repeat a 4.167 miles loop each hour; solo and paired entries are available, with 8 hour and 7 hour capped options and chip timing.

Inflatable obstacle course at Cheltenham Racecourse on 10 October 2026 with options from 2.5 km to 15 km, family rules for children, finishers medals and on-site facilities.

Trail races at Box Hill in Surrey with 21K, 31K and 50K options on marked routes. GPX files, chip timing and an event village with medals and post race food.

A guided half marathon through the Chiltern Hills covering about 13 miles with 300 m ascent, grouped by ability and led by qualified Run Leaders, including a refreshment point, finisher’s medal and Trees not Tees certificate.

A ten hour lap event at Pippingford Park where participants aim to complete ten laps of roughly three, four or five mile loops. Each lap must finish back at the race village within the hour and the final grade is set by the shortest loop co..

Woodland trail races in Epping Forest offering a half marathon and a 10K in October 2026, with marked courses, aid stations, chip timing and eco-friendly measures.

A military style obstacle mud run at Hever Castle on 10 and 11 October 2026 offering 3K, 6K and 12K routes with replica Commando obstacles, an event village and a 2-hour survival experience.

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.

A community-run event in Old Basing with chip-timed 10K and 6K trail races plus a 2K family fun run, raising funds for Friends of Old Basing Schools.

MacTuffX Swindon on 11 October 2026 at County Ground combines ten prescribed Xercises with repeated runs in Classic and 2X formats, offering solo, doubles and five-person relay entries for adults aged 18 and over.

A community off road running event in Marshfield on Sunday 11 October 2026 with children's and adult distances. Entries support Marshfield Primary School and the routes use temporary access across private land.

Black To The Trails 2026 brings family friendly and longer trail runs to Blaise Castle in Bristol on 11 October 2026, with 1K, 5K and 10K options and free entry for under 16s.

A nighttime backyard ultra from Vigo Rugby Club that sends runners repeatedly on a 4.167 mile loop, starting each hour. Options include an open-ended Backyard Ultra or a 7 hour Challenge, with buckle and medal awards plus a team prize.

Trail event at Burnbake Forest Lodges near Corfe Castle on 17 October 2026. Three marked routes of 24 km, 12 km and 6 km run on technical coastal and marshland trails with steep climbs, and outposts require a reusable cup.

A 100 mile continuous trail race based in Goring and Streatley that uses sections of the Ridgeway and Thames Path. The course consists of four 25 mile out and back spurs and features 16 aid stations and on-course medical support.

An annual 25 km and 50 km challenge walk, jog or run through footpaths and tracks in Kent, Surrey and Sussex on 17 October 2026. Entrants receive route files and have checkpoints, food and first aid included.

A guided 10 mile trail run around canals, reservoirs and Britain’s oldest post windmill near the Chilterns. Includes a run leader, trail technique instruction and a finisher’s medal; places are limited to 40.

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.