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Challenge walks in Isle of Wight in May 2026

Find challenge walks in Isle of Wight in May 2026 - filter by date, location or category, display on a map or use the advanced search to find your perfect race.

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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 this year!
  • Sat 2 - Sun 3 May
  • £39-£199
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge

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 this year!

  • Trail run 3
  • 50K ultra run 3
  • 100K ultra run 2
  • Ultra run
  • Families
  • Beginner-friendly
  • Entertainment
  • Music
  • Event village
  • Age 14 & over
Your chance to combine the beauty of the Isle of Wight Coastal Path with its sea views, glades and tall ridges, with your love of wild walking, and support those with brain cancer in each step.
  • Sat 16 - Sun 17 May
  • £20-£30
  • 50% off
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight

Your chance to combine the beauty of the Isle of Wight Coastal Path with its sea views, glades and tall ridges, with your love of wild walking, and support those with brain cancer in each step.

  • Charity walk 2
  • Rural
  • Coast
  • Sustainability policy
  • Public transport links
  • Age 18 & over

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