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Challenge walks in South East in September 2025

Find challenge walks near me in South East in September 2025 - search by date or place, display on a map or use the advanced search to find your perfect race.

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The full distance option of the South Coast Challenge from sunny Eastbourne, over the magnificent Seven Sisters, onto Cuckmere Haven and over the South Downs all the way to historic Arundel.
  • Sat 6 - Sun 7 Sep 2025
  • 11 charities
  • Sat 6 - Sun 7 Sep 2025
  • 11 charities
Polegate, East Sussex, UK

South Coast Ultra Challenge | Full 100km continuous charity places

The full distance option of the South Coast Challenge from sunny Eastbourne, over the magnificent Seven Sisters, onto Cuckmere Haven and over the South Downs all the way to historic Arundel.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 100 km trail running + 2100 m ascent
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.
  • Sat 6 - Sun 7 Sep 2025
  • 10 charities
  • Sat 6 - Sun 7 Sep 2025
  • 10 charities
Polegate, East Sussex, UK

South Coast Ultra Challenge | Full 100km over 2 days charity places

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
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.
  • Sat 6 Sep 2025
  • 11 charities
  • Sat 6 Sep 2025
  • 11 charities
Polegate, East Sussex, UK

South Coast Ultra Challenge | 1st Half charity places

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
The first quarter option of the South Coast Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckmere Haven, over the South Downs to finish at Alfriston.
  • Sat 6 Sep 2025
  • 11 charities
  • Sat 6 Sep 2025
  • 11 charities
Polegate, East Sussex, UK

South Coast Ultra Challenge | 1st Quarter charity places

The first quarter option of the South Coast Challenge from Eastbourne to the coastline, over the Seven Sisters to Cuckmere Haven, over the South Downs to finish at Alfriston.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 14 & over
  • 25 km trail running + 660 m ascent
The second half option of the South Coast Challenge is a scenic ‘marathon plus’ adventure across the South Downs towards Arundel.
  • Sat 6 - Sun 7 Sep 2025
  • 11 charities
  • Sat 6 - Sun 7 Sep 2025
  • 11 charities
Hove, East Sussex, UK

South Coast Ultra Challenge | 2nd Half charity places

The second half option of the South Coast Challenge is a scenic ‘marathon plus’ adventure across the South Downs towards Arundel.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 43 km trail running + 850 m ascent
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.
  • Sat 13 - Sun 14 Sep 2025
  • 11 charities
  • Sat 13 - Sun 14 Sep 2025
  • 11 charities
Egham, Surrey, UK

Thames Path Challenge | 2nd Half charity places

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
  • Undulating
  • Age 18 & over
  • 50 km trail running + 150 m ascent
The third quarter option of the Thames Path Challenge from Runnymede of Magna Carta Fame following the meandering waterway to finish at Cookham.
  • Sat 13 - Sun 14 Sep 2025
  • 11 charities
  • Sat 13 - Sun 14 Sep 2025
  • 11 charities
Egham, Surrey, UK

Thames Path Challenge | 3rd Quarter charity places

The third quarter option of the Thames Path Challenge from Runnymede of Magna Carta Fame following the meandering waterway to finish at Cookham.

  • Chip timing
  • Enter online
  • GPS tracking
  • Flat
  • Age 14 & over
  • 28 km trail running + 20 m ascent
The fourth quarter option of the Thames Path Challenge from Cookham along the meandering waterway to Henley-on-Thames, home of the regatta, to a fabulous celebration finish and family BBQ.
  • Wed 17 Sep 2025
  • 11 charities
  • Wed 17 Sep 2025
  • 11 charities
Maidenhead, Berkshire, UK

Thames Path Challenge | 4th Quarter charity places

The fourth quarter option of the Thames Path Challenge from Cookham along the meandering waterway to Henley-on-Thames, home of the regatta, to a fabulous celebration finish and family BBQ.

  • Chip timing
  • Enter online
  • GPS tracking
  • Flat
  • Age 14 & over
  • 22 km trail running + 10 m ascent
The full distance option of the Chiltern 50 Challenge from basecamp in Henley on a loop via Greys Court, the Ridgeway, Shakespeare's Way, The Chilterns and Hambleden Village.
  • Sat 27 Sep 2025
  • 10 charities
  • Sat 27 Sep 2025
  • 10 charities
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Ultra Challenge | Full 50km charity places

The full distance option of the Chiltern 50 Challenge from basecamp in Henley on a loop via Greys Court, the Ridgeway, Shakespeare's Way, The Chilterns and Hambleden Village.

  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 50 km trail running + 920 m ascent
The shorter 25km loop option of the Chiltern 50 Challenge from Henley Showground past the River Thames, Greys Court and the pretty Hambleden Village.
  • Sat 27 Sep 2025
  • 10 charities
  • Sat 27 Sep 2025
  • 10 charities
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Ultra Challenge | Henley 25km Loop charity places

The shorter 25km loop option of the Chiltern 50 Challenge from Henley Showground past the River Thames, Greys Court and the pretty Hambleden Village.

  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 500 m ascent

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