Trail runs in South East
Find trail runs near me in South East for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.
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Click an event for full event details, location, route, sustainability, what's included and how to enter.
- Sun 14 Sep
- £39
- 14 charities
- Sun 14 Sep
- £39
- 14 charities
The Henley 10K
A fabulous 10km loop through Remenham countryside with a start and finish near Henley Bridge on Sunday morning. Take it on as a walk, jog or run and get your family and friends involved!
- Chip timing
- Enter online
- Flat
- Age 15 & over
- 10 km trail running
- Wed 17 Sep
- £89
- 17 charities
- Wed 17 Sep
- £89
- 17 charities
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
- Sat 27 Sep
- £139
- 12 charities
- Sat 27 Sep
- £139
- 12 charities
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
- 12 charities
- Sat 27 Sep
- £89
- 12 charities
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
- 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
- £39
- 13 charities
- Sat 27 Sep
- £39
- 13 charities
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
- 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
- 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
- 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
- Sat 11 Oct
- £139
- 6 charities
- Sat 11 Oct
- £139
- 6 charities
Kent Downs 50 Ultra Challenge | 50km
Set in an Area of Outstanding Natural Beauty offering dramatic views, vibrant communities, a rich historic heritage, and diverse wildlife and habitats – featuring the North Downs Way National Trail.
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Age 16 & over
- 50 km trail running + 1000 m ascent
- Sat 11 Oct
- £89
- 6 charities
- Sat 11 Oct
- £89
- 6 charities
Kent Downs 50 Ultra Challenge | 25km
The 25km loop sits within the 50km loop and splits off at the picturesque village of Aylesford - one of the River Medway’s hidden jewels heading east on Augustine Camino to Detling via Boxley.
- Enter online
- GPS tracking
- Undulating
- Age 14 & over
- 25 km trail running + 450 m ascent
- Sat 11 Oct
- £39
- 6 charities
- Sat 11 Oct
- £39
- 6 charities
Kent Downs 50 Ultra Challenge | Maidstone 10K
The 10km loop sits within the 50km and 25km events and splits off at the Pilgrim Way returning to Detling via Boxley and back to the Kent Showground. You’ll be rewarded with a medal and glass of fizz!
- Enter online
- Undulating
- Age 8 & over
- 10 km trail running + 180 m ascent
- Sun 19 Oct
- £31
- Sun 19 Oct
- £31
Bedgebury Forest Half Marathon
An unforgettable race between the pines and beneath the majestic canopy of Bedgebury Forest - a trail race that will ignite your racer's heart.
- Chip timing
- Enter online
- Undulating
- Traffic free
- Age 17 & over
- 13.1 miles trail running
- Sun 19 Oct
- £7
- Sun 19 Oct
- £7
Bedgebury Forest Junior Race
A chip-timed run for aspiring junior racers! The race will take place before the main race, on the trails and paths around Bedgebury and will be fully marshalled.
- Chip timing
- Enter online
- Undulating
- Traffic free
- Age 9 & over
- 2 km trail running
- Sun 19 Oct
- £26
- Sun 19 Oct
- £26
Bedgebury Forest 10K
An unforgettable race between the pines and beneath the majestic canopy of Bedgebury Forest - a trail race that will ignite your racer's heart.
- Chip timing
- Enter online
- Undulating
- Traffic free
- Age 15 & over
- 10 km trail running
- Sat 25 Oct
- £70
- Sat 25 Oct
- £70
Thames Trail Ultra
This 47-mile point-to-point along England’s longest river is one of the most popular events in the British ultra running calendar, boasting an interesting route and top runner reviews.
- Newcomers
- Enter online
- GPS tracking
- Event village
- Rural
- Age 18 & over
- 47 miles trail running + 913 ft ascent
- Sun 2 Nov
- £46
- Sun 2 Nov
- £46
Wendover Woods Marathon
An autumnal trail treat to delight the senses and lift your spirit as you clock the miles and enjoy the majestic beauty of Wendover Forest. See you there!
- Enter online
- Undulating
- Age 18 & over
- 26.2 miles trail running + 2979 ft ascent
- Sun 2 Nov
- £25
- Sun 2 Nov
- £25
Wendover Woods 10K
An autumnal trail treat to delight the senses and lift your spirit as you clock the miles and enjoy the majestic beauty of Wendover Forest. See you there!
- Enter online
- Undulating
- Age 15 & over
- 10 km trail running + 721 ft ascent
- Sun 2 Nov
- £6
- Sun 2 Nov
- £6
Wendover Woods 1K
A fun 1K race for younger runners where all children who finish receive a medal! A wonderful, traffic-free event to inspire our younger people.
- Enter online
- Undulating
- All ages
- 1 km trail running
- Sun 2 Nov
- £30
- Sun 2 Nov
- £30
Wendover Woods Half Marathon
An autumnal trail treat to delight the senses and lift your spirit as you clock the miles and enjoy the majestic beauty of Wendover Forest. See you there!
- Enter online
- Undulating
- Age 17 & over
- 13.1 miles trail running + 1505 ft ascent
- Sun 23 Nov
- £24
- Sun 23 Nov
- £24
ATW Wendover Woods Trail Run | 5K Canicross
Set in the stunning Wendover Woods, this is the perfect chance to challenge yourself and your dog on scenic trails surrounded by woodland. Enjoy the fresh air, stunning views and rewarding trails.
- Enter online
- Undulating
- Traffic free
- Age 16 & over
- 5 km trail running + 338 ft ascent
- Sun 23 Nov
- £27
- Sun 23 Nov
- £27
ATW Wendover Woods Trail Run | 10K
Set in the stunning Wendover Woods, this is the perfect chance to challenge yourself over 10K on scenic trails surrounded by woodland. Enjoy the fresh air, stunning views and rewarding trails.
- Enter online
- Undulating
- Traffic free
- Age 15 & over
- 10 km trail running
- Sun 23 Nov
- £35
- Sun 23 Nov
- £35
ATW Wendover Woods Trail Run | Half Marathon
Set in the stunning Wendover Woods, this is the perfect chance to challenge yourself over half marathon distance on scenic trails. Enjoy the fresh air, stunning views and rewarding trails.
- Enter online
- Undulating
- Traffic free
- Age 17 & over
- 13.1 miles trail running
- Sun 23 Nov
- £19
- Sun 23 Nov
- £19
ATW Wendover Woods Trail Run | 5K
Set in the stunning Wendover Woods, this is the perfect opportunity to challenge yourself on scenic trails surrounded by beautiful woodland. Enjoy the fresh air, stunning views, and rewarding trails.
- Enter online
- Undulating
- Traffic free
- Age 11 & over
- 5 km trail running + 338 ft ascent
- Sat 10 Jan 2026
- £80
- Sat 10 Jan 2026
- £80
Country to Capital Ultra
A fabulous 43-mile point-to-point race, well established as the season opener to the Ultra race calendar and always sells out. From the countryside along the Grand Union Canal into London.
- Recycling
- Newcomers
- Chip timing
- Enter online
- GPS tracking
- Undulating
- Event village
- Age 18 & over
- 43 miles trail running + 1404 ft ascent