Challenge walks in South East
Find challenge walks 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.
- Sat 6 - Sun 7 Sep
- £199
- 14 charities
- Sat 6 - Sun 7 Sep
- £199
- 14 charities
South Coast Ultra Challenge | Full 100km over 2 days
The full distance option of the South Coast Challenge over 2 days with 57km on day 1 and 43km on day 2, meaning you experience the route in daylight with the chance to sleep overnight.
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 100 km trail running + 2100 m ascent
- Sat 6 Sep
- £139
- 15 charities
- Sat 6 Sep
- £139
- 15 charities
South Coast Ultra Challenge | 1st Half
The first half option of the South Coast Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckemere Haven, over the South Downs to finish via Brighton's promenade.
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 57 km trail running + 1250 m ascent
- Sat 6 Sep
- £89
- 15 charities
- Sat 6 Sep
- £89
- 15 charities
South Coast Ultra Challenge | 1st Quarter
The first quarter option of the South Coast Ultra Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckmere Haven, over the South Downs to finish at Alfriston for a celebration!
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 14 & over
- 25 km trail running + 660 m ascent
- Sat 6 - Sun 7 Sep
- £139
- 15 charities
- Sat 6 - Sun 7 Sep
- £139
- 15 charities
South Coast Ultra Challenge | 2nd Half
The second half option of the South Coast Ultra Challenge is a scenic ‘marathon plus’ adventure across the South Downs towards Arundel with wonderful coastal views and a celebratory finish!
- Chip timing
- Enter online
- GPS tracking
- Hilly
- Age 18 & over
- 43 km trail running + 850 m ascent
- Sat 13 Sep
- £169
- 18 charities
- Sat 13 Sep
- £169
- 18 charities
Thames Path Ultra Challenge | 3/4 Challenge
Start this epic 3/4 distance of the Thames Path Challenge near Hampton Court and follow the meandering waterway to Runnymede for a big celebration finish and hot meal at Henley on Thames.
- Chip timing
- Enter online
- GPS tracking
- Flat
- Age 18 & over
- 72 km trail running + 60 m ascent
- Sat 13 - Sun 14 Sep
- £139
- 18 charities
- Sat 13 - Sun 14 Sep
- £139
- 18 charities
Thames Path Ultra Challenge | 2nd Half
The second half option of the Thames Path Challenge from Runnymede along the meandering river through Cookham to Henley-on-Thames, home of the regatta, to a celebration finish and family BBQ!
- Chip timing
- Enter online
- GPS tracking
- Flat
- Age 18 & over
- 50 km trail running + 150 m ascent
- Sat 13 Sep
- £89
- 18 charities
- Sat 13 Sep
- £89
- 18 charities
Thames Path Ultra Challenge | 2nd Quarter
The second quarter event of the Thames Path Challenge takes a route from near Hampton Court and follows the meandering waterway to Runnymede of Magna Carta Fame, for a celebratory finish and hot meal!
- Chip timing
- Enter online
- Flat
- Age 14 & over
- 22 km trail running + 20 m ascent
- Sat 13 - Sun 14 Sep
- £89
- 18 charities
- Sat 13 - Sun 14 Sep
- £89
- 18 charities
Thames Path Ultra Challenge | 3rd Quarter
The epic third quarter option of the Thames Path Challenge starts from Runnymede of Magna Carta Fame following the meandering waterway to finish at Cookham to finish with a celebration and fizz at the
- Chip timing
- Enter online
- Flat
- Age 14 & over
- 28 km trail running + 20 m ascent
- Wed 17 Sep
- £89
- 18 charities
- Wed 17 Sep
- £89
- 18 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
- Fri 19 - Sun 21 Sep
- £65-£300
- Fri 19 - Sun 21 Sep
- £65-£300
Trailwalker
Are you Trailwalker strong? As a team of four, trek 100km non-stop across the South Downs in under 30 hours.
- Newcomers
- Enter online
- GPS tracking
- Fundraising required
- Hilly
- Event village
- Park
- Age 18 & over
- 100 km trekking
- Sat 27 Sep
- £139
- 13 charities
- Sat 27 Sep
- £139
- 13 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
- 13 charities
- Sat 27 Sep
- £89
- 13 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
- Sun 5 Oct
- £30
- Sun 5 Oct
- £30
The Palace Walk
Walk 13 miles around iconic Windsor landmarks with stunning views of Windsor Castle, followed by a Finish Festival to celebrate your huge achievement and receive your medal.
- Chip timing
- Enter online
- GPS tracking
- Fundraising required
- Age 14 & over
- 13 miles walking
- 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