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Challenge walks in South East in May 2026

Find challenge walks in South East 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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Discover the magic of this World Heritage Site and explore England’s largest area of outstanding natural beauty in the Cotswolds countryside on this charming20-mile walking adventure.
  • Sat 9 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 charming20-mile walking adventure.

  • 20 miles walking
  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & 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.

50% off in January

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

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