20 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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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 4 - Sun 5 May
  • £10-£40
  • Entries closed
  • Sat 4 - Sun 5 May
  • £10-£40
  • Entries closed
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
Help transform the future of breast cancer one step at a time at this iconic venue where you'll walk through beautiful woods and fields on a ramble-ready route then receive your medal!
  • Sat 11 May
  • £20
  • Sat 11 May
  • £20
Woodstock, Oxfordshire, UK

Pink Ribbon Walk | Blenheim Palace and the Cotswolds | 20 Mile

Help transform the future of breast cancer one step at a time at this iconic venue where you'll walk through beautiful woods and fields on a ramble-ready route then receive your medal!

  • Enter online
  • Fundraising required
  • Undulating
  • Age 16 & over
  • 20 miles
Entries close soon
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 25 - Sun 26 May
  • £10-£40
  • Entries close soon
  • Sat 25 - Sun 26 May
  • £10-£40
  • Entries close soon
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 2 Jun
  • £10-£15
  • Sun 2 Jun
  • £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
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 8 Jun
  • £25
  • Sat 8 Jun
  • £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.
  • Sun 9 Jun
  • £20
  • Sun 9 Jun
  • £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
Roam through glorious grasslands and villages, along riverbanks and coastal paths, where you'll be rewarded with breathtaking views from Beachy Head to help beat cancer step by step.
  • Sat 29 Jun
  • £30
  • Sat 29 Jun
  • £30
Polegate, East Sussex, UK

Big Hike | South Coast | Marathon

Roam through glorious grasslands and villages, along riverbanks and coastal paths, where you'll be rewarded with breathtaking views from Beachy Head to help beat cancer step by step.

  • Chip timing
  • Enter online
  • Fundraising required
  • Hilly
  • Age 16 & over
  • 25.7 miles hiking + 2469 ft ascent
Roam through glorious grasslands and villages, along riverbanks and coastal paths, where you'll be rewarded with breathtaking views from Beachy Head to help beat cancer step by step.
  • Sat 29 Jun
  • £25
  • Sat 29 Jun
  • £25
Polegate, East Sussex, UK

Big Hike | South Coast | Half Marathon

Roam through glorious grasslands and villages, along riverbanks and coastal paths, where you'll be rewarded with breathtaking views from Beachy Head to help beat cancer step by step.

  • Chip timing
  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 13.1 miles hiking + 1297 ft 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 13 Jul
  • £25
  • Sat 13 Jul
  • £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.
  • Sun 14 Jul
  • £20
  • Sun 14 Jul
  • £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
A fabulous charity challenge setting out from Guildford base camp on a looped route taking in some of the best of the Surrey hills, the North Downs Way, and the surrounding countryside.
  • Sat 27 Jul
  • £10-£40
  • 7 charities
  • Sat 27 Jul
  • £10-£40
  • 7 charities
Guildford, Surrey, UK

North Downs 50 Ultra Challenge

A fabulous charity challenge setting out from Guildford base camp on a looped route taking in some of the best of the Surrey hills, the North Downs Way, and the surrounding countryside.

  • Newcomers
  • Entertainment
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Rural
  • Age 14 & over
  • 50 km road running
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 7 - Sun 8 Sep
  • £10-£40
  • 8 charities
  • Sat 7 - Sun 8 Sep
  • £10-£40
  • 8 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
Explore one of the UK’s most beautiful National Parks with its pretty riverside paths, rolling hills, white coastal cliffs and the famous South Downs Way, with charity #TeamPassage.
  • Sat 14 Sep
  • £25
  • Sat 14 Sep
  • £25
Lewes, East Sussex, UK

South Downs Trekathon | The Passage

Explore one of the UK’s most beautiful National Parks with its pretty riverside paths, rolling hills, white coastal cliffs and the famous South Downs Way, with charity #TeamPassage.

  • Families
  • Newcomers
  • Plastic bottle free
  • Enter online
  • Fundraising required
  • Hilly
  • Rural
  • Coast
  • Sustainability policy
  • Public transport links
  • Age 12 & over
  • 1 day hiking
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
  • 6 charities
  • Sat 28 Sep
  • £10-£30
  • 6 charities
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
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
  • 3 charities
  • Sat 12 Oct
  • £10-£30
  • 3 charities
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
  • Sun 12 May
Winchester, Hampshire, UK

Breast Walk Ever | Hampshire | Marathon

  • 26 miles hiking + 2300 ft ascent
  • Sun 12 May
Winchester, Hampshire, UK

Breast Walk Ever | Hampshire | Half Marathon

  • 13 miles + 1000 ft ascent
  • Sat 18 May
Reading, Berkshire, UK

Goring Gap Trail Weekender | Half Marathon Walk

  • 50 km multi terrain running
  • Sun 15 Sep
Wallingford, Oxfordshire, UK

Breast Walk Ever | Oxfordshire | Marathon

  • 26 miles hiking
  • Sun 15 Sep
Wallingford, Oxfordshire, UK

Breast Walk Ever | Oxfordshire | Half Marathon

  • 13 miles

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