14

Challenge walks in South East in May 2025

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

Search by month

Search by place

Map

Events near me

Click an event for full event details, location, route, sustainability, what's included and how to enter.

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

Search by month

Search by place

Map

Search options

Back to search options