7 Challenge walks in Isle of Wight

Find challenge walks in and around Isle of Wight for 2023/2024 - filter events by date, display on a map or use the advanced search to find your perfect race.

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26 or 50 mile challenge walks 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 13 - Sun 14 Apr 2024
  • £10-£20
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight

26 or 50 mile challenge walks 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!

  • 1 day hiking
  • Enter online
  • Fundraising required
  • Undulating
  • Rural
  • Coast
  • Public transport links
  • Age 18 & over
  • Challenge walks
An epic challenge, making a full 106km circuit of the Isle of Wight, starting and finishing in Chale, enjoy well stocked rest stops and superb scenery every step of the way.
  • Sun 5 May 2024
  • £198
  • 8 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | Full 106km continuous

An epic challenge, making a full 106km circuit of the Isle of Wight, starting and finishing in Chale, enjoy well stocked rest stops and superb scenery every step of the way.

  • 106 km multi terrain running + 1960 m ascent
  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 100K ultra runs
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.
  • Sun 5 - Mon 6 May 2024
  • £198
  • 8 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | Full 106km over 2 days

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.

  • 106 km multi terrain running + 1960 m ascent
Take on a 25km challenge along the trails of the southern coast of the Isle of Wight, finishing by The Needles for a BBQ lunch.
  • Sun 5 May 2024
  • £79
  • 8 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | 1st Quarter

Take on a 25km challenge along the trails of the southern coast of the Isle of Wight, finishing by The Needles for a BBQ lunch.

  • 25 km trail running + 660 m ascent
  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • Trail runs
The first half of the Isle of Wight circuit explore 52km of scenic coastal trails, enjoy spectacular coastal views along the undulating route with plenty of rest stops to keep you well fuelled.
  • Sun 5 May 2024
  • £129
  • 8 charities
Ventnor, Isle of Wight, UK

Isle of Wight Challenge | 1st Half

The first half of the Isle of Wight circuit explore 52km of scenic coastal trails, enjoy spectacular coastal views along the undulating route with plenty of rest stops to keep you well fuelled.

  • 54 km trail running + 1100 m ascent
  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 16 & over
  • 50K ultra runs
Starting in Cowes, follow a clockwise route along the eastern side of the Isle of Wight, enjoying superb coastal views en route to the finish line at Chale.
  • Mon 6 May 2024
  • £129
  • 8 charities
Cowes, Isle of Wight, UK

Isle of Wight Challenge | 2nd Half

Starting in Cowes, follow a clockwise route along the eastern side of the Isle of Wight, enjoying superb coastal views en route to the finish line at Chale.

  • 52 km trail running + 980 m ascent
Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.
  • Mon 6 May 2024
  • £79
  • 8 charities
Sandown, Isle of Wight, UK

Isle of Wight Challenge | 4th Quarter

Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.

  • 25 km trail running + 480 m ascent
  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • Trail runs