Trail runs in South East
Find trail runs near me in South East for 2025/2026 - filter by date or location, display on a map or use the advanced search to find your perfect race.
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Select an event for photos, video, route, location, reviews, entry fees and how to enter.
- Wed 17 Sep
- £89
Thames Path Ultra Challenge | 4th Quarter
The epic fourth quarter option of the Thames Path Challenge starts in gorgeous Cookham and follows the meandering waterway to Henley-on-Thames, home of the regatta, to a fabulous celebration finish!
- Chip timing
- Enter online
- Flat
- Age 14 & over
- 22 km trail running + 10 m ascent
- Sun 21 Sep
- £16-£18
Fraggle Run | 3K
Come and join the day of running and aim to complete a 3K at your own pace on a scenic course then receive a themed medal and goody bag at the finish!
- Enter online
- Flat
- Traffic free
- All ages
- 3 km trail running + 0 ft ascent
- Sun 21 Sep
- £23-£27
Fraggle Run | 5K
Come and join the day of running and aim to complete a 5K at your own pace on a scenic course then receive a fantastic themed medal and goody bag at the finish!
- Enter online
- Flat
- Traffic free
- Age 12 & over
- 5 km trail running + 0 ft ascent
- Sun 21 Sep
- £23-£27
Fraggle Run | 10K
Come and join the day of running and aim to complete a 10K at your own pace on a scenic course then receive a fantastic themed medal and goody bag at the finish!
- Enter online
- Flat
- Traffic free
- Age 16 & over
- 10 km trail running + 0 ft ascent
- Sun 21 Sep
- £23-£35
Fraggle Run | Half Marathon
Welcome to a 7-hour timed running event where you can run a half marathon at your own pace on an out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 17 & over
- 13.1 miles trail running + 0 ft ascent
- Sun 21 Sep
- £23-£35
Fraggle Run | Marathon
Welcome to a 7-hour timed running event where you can run a marathon at your own pace on an out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 18 & over
- 26.2 miles trail running + 0 ft ascent
- Sun 21 Sep
- £23-£35
Fraggle Run | 50K
Welcome to a 7-hour timed running event where you can run 50K within the time limit on a scenic out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 20 & over
- 50 km trail running + 0 ft ascent
- Sun 21 Sep
- £23-£35
Fraggle Run | Ultra Marathon
Welcome to a 7-hour timed running event where you can run an ultra at your own pace on an out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 18 & over
- 30.6 miles trail running + 0 ft ascent
- Sun 21 Sep
- £23-£35
Fraggle Run | Time Challenge
Welcome to a 7-hour timed running event where you can run as far as you can in 7 hours at your own pace on a scenic route, with fuel stations each lap, and a themed medal and goody bag!
- Enter online
- Flat
- Traffic free
- Age 20 & over
- 7 hrs trail running + 0 ft ascent
- Sat 27 Sep
- £139
Chiltern 50 Ultra Challenge | Full 50km
The full 50K route of the Chiltern 50 Ultra Challenge starts from basecamp in Henley on a loop via Greys Court, the Ridgeway, Shakespeare's Way, The Chilterns and Hambleden Village to a party finish!
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Age 18 & over
- 50 km trail running + 920 m ascent
- Sat 27 Sep
- £89
Chiltern 50 Ultra Challenge | Henley 25km Loop
An exciting 25km loop as part of the Chiltern 50 Ultra Challenge from Henley Showground past the River Thames, Greys Court and the pretty Hambleden Village to a celebratory finish!
- Enter online
- GPS tracking
- Undulating
- Age 14 & over
- 25 km trail running + 500 m ascent
- Sat 27 Sep
- £75
Fortitude Ultra | Denbies
10Hrs: 10 Laps: You-vs-You. Complete 10 laps of the ~3-mile, 4-mile or 5-mile loops in the given time through the scenic Denbies Wine Estate.
- Newcomers
- Enter online
- Hilly
- Traffic free
- Event village
- Rural
- Free venue entry
- Sustainability policy
- Age 20 & over
- 10 hrs trail running
- Sat 27 Sep
- £16-£18
Romp Run | 3K
Come and join the day of running and aim to complete a 3K at your own pace on a scenic course then receive a fantastic themed medal and goody bag at the finish!
- Enter online
- Flat
- Traffic free
- All ages
- 3 km trail running
- Sat 27 Sep
- £23-£27
Romp Run | 5K
Come and join the day of running and aim to complete a 5K at your own pace on a scenic out-and-back course then receive a fantastic themed medal and goody bag at the finish!
- Enter online
- Flat
- Traffic free
- Age 12 & over
- 5 km trail running + 0 ft ascent
- Sat 27 Sep
- £23-£27
Romp Run | 10K
Come and join the day of running and aim to complete a 10K at your own pace on a scenic out-and-back course then receive a fantastic themed medal and goody bag at the finish!
- Enter online
- Flat
- Traffic free
- Age 16 & over
- 10 km trail running + 0 ft ascent
- Sat 27 Sep
- £23-£35
Romp Run | Half Marathon
Welcome to a 7-hour timed running event where you can run a half marathon at your own pace on an out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 17 & over
- 13.1 miles trail running + 0 ft ascent
- Sat 27 Sep
- £23-£35
Romp Run | Marathon
Welcome to a 7-hour timed running event where you can run a marathon at your own pace on an out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 18 & over
- 26.2 miles trail running + 0 ft ascent
- Sat 27 Sep
- £23-£35
Romp Run | 50K
Welcome to a 7-hour timed running event where you can run 50K within the time limit on a scenic out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 20 & over
- 50 km trail running + 0 ft ascent
- Sat 27 Sep
- £23-£35
Romp Run | Ultra Marathon
Welcome to a 7-hour timed running event where you can run an ultra at your own pace on an out-and-back route, with fuel stations each lap, and a medal and goody bag at the finish.
- Enter online
- Flat
- Traffic free
- Age 18 & over
- 30.6 miles trail running + 0 ft ascent
- Sat 27 Sep
- £23-£35
Romp Run | Time Challenge
Welcome to a 7-hour timed running event where you can run as far as you can in 7 hours at your own pace on a scenic route, with fuel stations each lap, and a themed medal and goody bag!
- Enter online
- Flat
- Traffic free
- Age 18 & over
- 7 hrs trail running + 0 ft ascent
- Sat 27 Sep
- £39
The Chiltern 10K
A beautiful 10km loop from the basecamp at Henley Showground exploring public footpaths and wonderful woodlands within the Culden Faw estate to be rewarded with a medal and glass of fizz!
- Enter online
- Undulating
- Age 15 & over
- 10 km trail running + 235 m ascent
- Sun 28 Sep
- £65-£80
Hever Castle | Marathon
Get active in the award-winning grounds and surrounding Kent countryside in a full marathon! Recruit your friends and celebrate completing your challenge in the festival village.
- Chip timing
- Enter online
- Relay
- Age 18 & over
- 42.2 km trail running
- Sun 28 Sep
- £45
Hever Castle | Half Marathon
Get active in the award-winning grounds and surrounding Kent countryside in a half marathon! Recruit your friends and celebrate completing your challenge in the festival village.
- Chip timing
- Enter online
- Age 17 & over
- 21.1 km trail running
- Sun 28 Sep
- £35
Hever Castle | 10K
Get active in the award-winning grounds and surrounding Kent countryside in a 10K run! Recruit your friends to join in then celebrate completing your challenge in the festival village.
- Chip timing
- Enter online
- Age 15 & over
- 10 km trail running
- Fri 3 Oct
- £16-£18
Midweek Chasing Numbers Oct | 3K
The aim of the midweek runs is to hold events as cheaply as possible in order for people to be able to build their numbers or simply to help people achieve their own goals at an affordable price.
- Enter online
- All ages
- 3 km trail running + 0 ft ascent