Challenge walks in South East in September 2025
Find challenge walks near me in South East in September 2025 - filter by date or location, display on a map or use the advanced search to find your perfect race.
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- Sat 13 Sep
- £169
- Entries closed
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
- Entries closed
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
- Entries closed
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
- Entries closed
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
- Entries closed
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
- £75-£300
- Entries closed
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
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- Sat 27 Sep
- £25
Mighty Hikes | South Coast | Marathon
Take on a challenge and join Macmillan at the South Coast Mighty Hike - where you’ll explore the stunning South Downs Way and take in spectacular coastal views to support people living with cancer.
- Enter online
- Fundraising required
- Hilly
- Age 14 & over
- 26.2 miles hiking + 964.73 m 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
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- Sat 27 Sep
- £20
Mighty Hikes | South Coast | Half Marathon
Take on a challenge and join Macmillan at the South Coast Mighty Hike - where you’ll explore the stunning South Downs Way and take in spectacular coastal views to support people living with cancer.
- Enter online
- Fundraising required
- Hilly
- Age 14 & over
- 13 miles hiking + 481.14 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
- Sun 14 Sep
The Great Southern Walk | 15 Mile Challenge Walk
- 15 miles walking + 1300 ft ascent