Trail Running Calendar South East (England) 2026-2027

A 100K trail race on an anticlockwise loop of the Chiltern Hills, starting and finishing in Chesham and passing The Ridgeway, Ashridge Estate and other landmarks. Fully marked with open GPS tracking and organised support at aid stations.

A point to point 50 km ultramarathon from Horsham to Brighton seafront on 9 May 2026, featuring multi terrain trails, four feed stations and a 9.5 hour cut off. Individual and two runner relay entries are offered with team prizes.

Goring Gap Trails offers ultramarathon, half marathon and walking distances near Reading on 9 and 10 May 2026. The TRA licensed event includes affiliated and unaffiliated entry options and on site camping.

An inflatable obstacle-course event at Stoke Park, Guildford on 9 May 2026 offering 2.5k, 5k, 10k and 15k lap options with large inflatables, music zones, a finisher medal and family and charity entry choices.

Test your endurance at Stanmer Park by completing 4.167 miles every hour until only one runner remains. This out and back course offers a personal challenge with support facilities and refreshments for all participants.

Riverside lapped races from Wraysbury Skiff & Punting Club near Runnymede, with 10 km, half marathon and marathon options along the Thames Path. The marked route includes marshals, a bespoke finisher medal and podium prizes.

Experience the twilight beauty of Ardingly Reservoir during this evening run in West Sussex. Choose between a 5K or 10K distance on an undulating trail course featuring scenic water views and a finisher medal.

A camp-based Backyard Ultra at Chilton Manor Farm featuring a repeated loop through private trails, fields and woodland with a high point at Bugmore Hill Trig Point and on-site aid, toilets and course photography.

Off road 10k, 5k and junior races at Milton Creek Country Park on 10 May 2026 raising funds for the Oliver Fisher Special Care Baby Trust. The stone trail route includes hills and pacers for the 10k, with medals and photos.

Run two laps or one around the undulating Rathfinny Wine Estate trails. The off-road course features grass, wooded sections and marked aid stations while supporting the WOLO Foundation and reducing single-use plastics.

Trail races in the South Downs around Cocking on 10 May 2026, offering 10 km and 20 km senior courses plus 3 km and 5 km junior races on mostly off road trails with water stations, marshals and age category awards.

Hairy Legs is an all ages cross-country event at Sheepcot Recreation Ground on 10 May 2026, with children's laps, teenage and adult loops plus solo and relay options, and proceeds supporting two local primary schools.

A one lap *10 km* trail through Hampton Estate and Puttenham Common with undulating hills and bluebell woods. Chip timing, finish medals and on-site parking, with food and refreshments available at the finish.

A community 5k trail run and walk around East Hendred with a separate 1k kids event on the Sportsground. Entries are limited and close on 8 May 2026.

A four evening summer series at Dinton Pastures with 5 km and 10 km races plus a 2 km kids event. Off road and traffic free, the series offers chip timing, finisher medals, instant results and on site first aid.

A 50 mile point to point run on the North Downs Way from Farnham to Knockholt Pound with 5,600 ft of climb, six aid stations and a 13 hour limit. Entry requires a prior marathon finish within that race’s cut off.

The Twenty Sixth Compton Downland Challenge in Compton, Berkshire on 16 May 2026 features a full marathon and a 16 mile race with a seven hour time limit; route maps, elevation profiles and videos are provided.

An inflatable obstacle course at Brands Hatch on 16 May 2026 offering laps of a 2.5 km circuit with 2.5 km, 5 km, 10 km and 15 km options, music zones, water stations and a finisher medal.

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

A weekend obstacle race in Henley on Thames on May 16-17, 2026, featuring Sprint, Super and Beast distances plus a Kids Race and spectator tickets, run along historic town landmarks and a riverside course.