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Challenge walks in South East

Find challenge walks near me in South East for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.

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Make it an active Easter on a challenge from Windsor Racecourse on looped routes through the Great Park with fantastic views of the castle, to Runnymede along the Thames Path.
  • Sat 12 Apr
  • £139
  • Sat 12 Apr
  • £139
Windsor, Berkshire, UK

Easter 50 Ultra Challenge | 50km

Make it an active Easter on a challenge from Windsor Racecourse on looped routes through the Great Park with fantastic views of the castle, to Runnymede along the Thames Path.

  • Enter online
  • GPS tracking
  • Undulating
  • Age 16 & over
  • 50 km trail running + 320 m ascent
Make it an active Easter on a challenge from Windsor Racecourse on looped routes through the Great Park with fantastic views of the castle, to Runnymede along the Thames Path.
  • Sat 12 Apr
  • £89
  • Sat 12 Apr
  • £89
Windsor, Berkshire, UK

Easter 50 Ultra Challenge | 25km

Make it an active Easter on a challenge from Windsor Racecourse on looped routes through the Great Park with fantastic views of the castle, to Runnymede along the Thames Path.

  • Enter online
  • Undulating
  • Age 14 & over
  • 25 km trail running + 175 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Half

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 52 km trail running + 900 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £199
  • 13 charities
  • Sat 3 May
  • £199
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full Continuous

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 106 km multi terrain running + 1800 m ascent
The full 106km circumnavigation of the Isle of Wight, in daylight hours. Overnight at Cowes for a well-earned rest on this wonderful exploration of the coastal routes around the island.
  • Sat 3 - Sun 4 May
  • £199
  • 13 charities
  • Sat 3 - Sun 4 May
  • £199
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full 2 Day Daylight

The full 106km circumnavigation of the Isle of Wight, in daylight hours. Overnight at Cowes for a well-earned rest on this wonderful exploration of the coastal routes around the island.

  • Chip timing
  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 106 km multi terrain running + 1960 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Southern 50

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 50 km trail running + 1025 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £89
  • 13 charities
  • Sat 3 May
  • £89
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Quarter

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 500 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Cowes, Isle of Wight, UK

Isle of Wight Ultra Challenge | 2nd Half

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 54 km trail running + 1000 m ascent
Start at the showground basecamp and follow the trails around the estuary, cross on the chain ferry and get a good feel for Cowes and its surrounding area.
  • Sat 3 May
  • £39
  • 13 charities
  • Sat 3 May
  • £39
  • 13 charities
Ventnor, Isle of Wight, UK

Medina 10 Mile

Start at the showground basecamp and follow the trails around the estuary, cross on the chain ferry and get a good feel for Cowes and its surrounding area.

  • Enter online
  • Flat
  • Age 8 & over
  • 10 miles trail running
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sun 4 May
  • £89
  • 13 charities
  • Sun 4 May
  • £89
  • 13 charities
Sandown, Isle of Wight, UK

Isle of Wight Ultra Challenge | 4th Quarter

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 500 m ascent
Discover the magic of this World Heritage Site and explore England’s largest area of outstanding natural beauty in the Cotswolds countryside on this charming walking adventure.
  • Sat 10 May
  • £25
  • Sat 10 May
  • £25
Woodstock, Oxfordshire, UK

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

Discover the magic of this World Heritage Site and explore England’s largest area of outstanding natural beauty in the Cotswolds countryside on this charming walking adventure.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 20 miles walking
A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!
  • Sat 17 May
  • £20
  • Sat 17 May
  • £20
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight | One Day Challenge

A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!

  • Enter online
  • Fundraising required
  • Undulating
  • Age 18 & over
  • 25 miles walking
A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!
  • Sat 17 - Sun 18 May
  • £30
  • Sat 17 - Sun 18 May
  • £30
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight | Two Day Challenge

A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!

  • Enter online
  • Fundraising required
  • Undulating
  • Age 18 & over
  • 50 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
  • £25
  • Sun 18 May
  • £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
  • £25
  • Sun 18 May
  • £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
A new 25km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the South Downs Way with its fabulous views back over the Sussex countryside.
  • Sun 25 May
  • £89
  • 14 charities
  • Sun 25 May
  • £89
  • 14 charities
Brighton, East Sussex, UK

Brighton Challenge

A new 25km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the South Downs Way with its fabulous views back over the Sussex countryside.

  • Enter online
  • Undulating
  • Hilly
  • Age 14 & over
  • 25 km trail running + 400 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
  • £25
  • Sat 7 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 + 964.73 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
  • £20
  • Sat 7 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 + 481.14 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
  • £10-£15
  • Sun 8 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 walking
Join a mid-summer North Downs 50 Challenge! This looped route is set in an area of outstanding natural beauty of the Surrey Hills, taking in chalk ridges and ancient woodlands.
  • Sat 12 Jul
  • £139
  • Sat 12 Jul
  • £139
Guildford, Surrey, UK

North Downs 50 Ultra Challenge | 50km

Join a mid-summer North Downs 50 Challenge! This looped route is set in an area of outstanding natural beauty of the Surrey Hills, taking in chalk ridges and ancient woodlands.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 50 km trail running + 830 m ascent
The 25km looped challenge sets out from Guildford early Saturday morning, along some of the most picturesque parts of the Surrey Hills Way – with a rest stop at half way with snacks and drinks.
  • Sat 12 Jul
  • £89
  • 1 charity
  • Sat 12 Jul
  • £89
  • 1 charity
Guildford, Surrey, UK

North Downs 50 Ultra Challenge | 25km Loop

The 25km looped challenge sets out from Guildford early Saturday morning, along some of the most picturesque parts of the Surrey Hills Way – with a rest stop at half way with snacks and drinks.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 530 m ascent
Follow the North Downs Way to Dorking for a 24km challenge with fabulous views. You’ll get full support all the way, rest stops en route and a picnic lunch at the finish.
  • Sat 12 Jul
  • £89
  • 1 charity
  • Sat 12 Jul
  • £89
  • 1 charity
Guildford, Surrey, UK

North Downs 50 Ultra Challenge | 1st Half

Follow the North Downs Way to Dorking for a 24km challenge with fabulous views. You’ll get full support all the way, rest stops en route and a picnic lunch at the finish.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 24 km trail running + 600 m ascent
Entries closed
Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.
  • Sat 19 Jul
  • £25
  • Entries closed
  • Sat 19 Jul
  • £25
  • Entries closed
Woodstock, Oxfordshire, UK

Mighty Hikes | Cotswolds | Marathon

Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 25.24 miles hiking + 452.61 m ascent
Entries closed
Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.
  • Sat 19 Jul
  • £20
  • Entries closed
  • Sat 19 Jul
  • £20
  • Entries closed
Chipping Norton, Oxfordshire, UK

Mighty Hikes | Cotswolds | Half Marathon

Take on a challenge and join Macmillan at the Cotswolds Mighty Hike - where you'll wander through peaceful chocolate box villages and along riverside paths to support people living with cancer.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 13.38 miles hiking + 285.55 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
  • £25
  • Sat 26 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
  • 25.4 miles hiking + 292.18 m ascent

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