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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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An end-of-season looped charity challenge in some of the Chilterns' finest countryside, with historic trails, rolling hills, nature reserves and fantastic views with routes from 10km up to 50km.
  • Sat 28 Sep
  • £10-£30
  • Entries closed
  • Sat 28 Sep
  • £10-£30
  • Entries closed
Henley-on-Thames, Buckinghamshire, UK

Chiltern 50 Ultra Challenge

An end-of-season looped charity challenge in some of the Chilterns' finest countryside, with historic trails, rolling hills, nature reserves and fantastic views with routes from 10km up to 50km.

  • Newcomers
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Hilly
  • Event village
  • Urban
  • Rural
  • Age 14 & over
  • 1 day trail running
Entries close soon
New for 2024! Walk with the Prince's Trust around iconic Windsor landmarks with amazing views of the castle, followed by a festival finish to celebrate your huge achievement and receive your medal.
  • Sun 6 Oct
  • £35
  • Entries close soon
  • Sun 6 Oct
  • £35
  • Entries close soon
Windsor, Berkshire, UK

The Palace Walk

New for 2024! Walk with the Prince's Trust around iconic Windsor landmarks with amazing views of the castle, followed by a festival finish to celebrate your huge achievement and receive your medal.

  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Age 14 & over
  • 13 miles
Entries closed
An end-of-season charity challenge in the Garden of England with a looped route around the Kent Downs starting on the North Downs Way with picturesque scenery and full support all the way.
  • Sat 12 Oct
  • £10-£30
  • Entries closed
  • Sat 12 Oct
  • £10-£30
  • Entries closed
Maidstone, Kent, UK

Kent Downs 50 Ultra Challenge

An end-of-season charity challenge in the Garden of England with a looped route around the Kent Downs starting on the North Downs Way with picturesque scenery and full support all the way.

  • Newcomers
  • Entertainment
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Event village
  • Rural
  • Age 14 & over
  • 1 day trail running
Walk, jog or run the stunning coastal paths of the Isle of Wight for a great charity cause, from the base camp at Chale, visiting historic Cowes and the iconic Needles en route.
  • Sat 3 - Sun 4 May 2025
  • £10-£40
  • 5 charities
  • Sat 3 - Sun 4 May 2025
  • £10-£40
  • 5 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge

Walk, jog or run the stunning coastal paths of the Isle of Wight for a great charity cause, from the base camp at Chale, visiting historic Cowes and the iconic Needles en route.

  • Newcomers
  • Entertainment
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Age 14 & over
  • 1 day trail running
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
  • Sun 18 May 2025
  • £25
  • Sun 18 May 2025
  • £25
Epsom, Surrey, UK

Poppy Hike | Medium

Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.

  • Enter online
  • Fundraising required
  • Age 18 & over
  • 15 miles
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
  • Sun 18 May 2025
  • £25
  • Sun 18 May 2025
  • £25
Epsom, Surrey, UK

Poppy Hike | Long

Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.

  • Enter online
  • Fundraising required
  • Age 18 & over
  • 21 miles
Walk, jog or run along the capital to coast route for charity, with a range of distance options available and superb support all the way, for all abilities and experience levels.
  • Sat 24 - Sun 25 May 2025
  • £10-£40
  • 8 charities
  • Sat 24 - Sun 25 May 2025
  • £10-£40
  • 8 charities
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge

Walk, jog or run along the capital to coast route for charity, with a range of distance options available and superb support all the way, for all abilities and experience levels.

  • Entertainment
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Age 14 & over
  • 1 day trail running
Now in its 17th year, this wonderfully popular walk takes you off the beaten track through some of Hampshire and Wiltshire's most beautiful countryside to support two local hospices.
  • Sun 8 Jun 2025
  • £10-£15
  • Sun 8 Jun 2025
  • £10-£15
Winchester, Hampshire, UK

Clarendon Way Walk | Classic Clarendon

Now in its 17th year, this wonderfully popular walk takes you off the beaten track through some of Hampshire and Wiltshire's most beautiful countryside to support two local hospices.

  • Enter online
  • Fundraising required
  • Age 8 & over
  • 26 miles
The South Downs National Park is a superb backdrop for a real charity challenge featuring Beachy Head, the Seven Sisters and the South Downs Way with a choice of distances from 25km right up to 100km!
  • Sat 6 - Sun 7 Sep 2025
  • £30-£50
  • 15 charities
  • Sat 6 - Sun 7 Sep 2025
  • £30-£50
  • 15 charities
Eastbourne, East Sussex, UK

South Coast Ultra Challenge

The South Downs National Park is a superb backdrop for a real charity challenge featuring Beachy Head, the Seven Sisters and the South Downs Way with a choice of distances from 25km right up to 100km!

  • Newcomers
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Urban
  • Rural
  • Coast
  • Age 14 & over
  • 1 day trail running
  • Sun 13 Oct
Lyndhurst, Hampshire, UK

RuckFit UK Intermediate Level Challenge | New Forest 1

  • 9 miles
  • Sat 12 Apr 2025
Windsor, Berkshire, UK

Easter 50 Ultra Challenge

  • 1 day trail running

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