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Challenge walks in Scotland in May 2025

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

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Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.
  • Sat 17 May 2025
  • £25
  • Sat 17 May 2025
  • £25
Callander, Stirling, UK

Big Hike | The Trossachs | Marathon

Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.

  • Chip timing
  • Enter online
  • Fundraising required
  • Hilly
  • Age 16 & over
  • 26.2 miles hiking + 2000 ft ascent
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in the City of Discovery over a challenging 20 mile route.
  • Sat 17 May 2025
  • 3 charities
  • Sat 17 May 2025
  • 3 charities
Dundee, Dundee City, UK

The Kiltwalk Dundee | Mighty Stride charity places

Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in the City of Discovery over a challenging 20 mile route.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 21.5 miles walking
Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.
  • Sat 17 May 2025
  • £20
  • Sat 17 May 2025
  • £20
Callander, Stirling, UK

Big Hike | The Trossachs | Half Marathon

Venture to the exquisite landscapes of Loch Lomond and The Trossachs National Park, through Callander and past stunning Lochs and waterfalls to help beat cancer step by step.

  • Chip timing
  • Enter online
  • Fundraising required
  • Undulating
  • Age 14 & over
  • 13.1 miles hiking + 1100 ft ascent

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