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Challenge walks in South East

Find challenge walks near me in South East for 2024/2025 - 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 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 walking
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 walking
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
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.
  • Sat 7 Jun 2025
  • £25
  • Sat 7 Jun 2025
  • £25
Brighton, East Sussex, UK

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 m ascent
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.
  • Sat 7 Jun 2025
  • £20
  • Sat 7 Jun 2025
  • £20
Polegate, East Sussex, UK

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 + 495.3 m ascent
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 walking
Take on a challenge and join Macmillan at the Thames Path Mighty Hike - where you'll hike from Windsor Racecourse along the most iconic river in England to support people living with cancer.
  • Sat 26 Jul 2025
  • £25
  • Sat 26 Jul 2025
  • £25
Windsor, Berkshire, UK

Mighty Hikes | Thames Path | Marathon

Take on a challenge and join Macmillan at the Thames Path Mighty Hike - where you'll hike from Windsor Racecourse along the most iconic river in England to support people living with cancer.

  • Enter online
  • Fundraising required
  • Flat
  • Age 14 & over
  • 26.1 miles hiking + 117 m ascent
Take on a challenge and join Macmillan at the Thames Path Mighty Hike - where you'll hike from Windsor Racecourse along the most iconic river in England to support people living with cancer.
  • Sat 26 Jul 2025
  • £20
  • Sat 26 Jul 2025
  • £20
Windsor, Berkshire, UK

Mighty Hikes | Thames Path | Half Marathon

Take on a challenge and join Macmillan at the Thames Path Mighty Hike - where you'll hike from Windsor Racecourse along the most iconic river in England to support people living with cancer.

  • Enter online
  • Fundraising required
  • Flat
  • Age 14 & over
  • 12.8 miles hiking + 73 m ascent
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
  • 14 charities
  • Sat 6 - Sun 7 Sep 2025
  • £30-£50
  • 14 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 walking
  • Sun 23 Mar 2025
Redhill, Surrey, UK

Y2Y North Downs Trek / Run | Marathon Challenge Trek

  • 26.2 miles walking
  • Sat 12 Apr 2025
Windsor, Berkshire, UK

Easter 50 Ultra Challenge

  • 1 day trail running

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