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Challenge walks in North Yorkshire

Find challenge walks in North Yorkshire in 2026/2027 - filter by date, location or category, display on a map or use the advanced search to find your perfect race.

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Select an event for photos, video, route, location, reviews, entry fees and how to enter.

Hike through the heart of the Yorkshire Dales, with its rolling green hills, drystone walls, and the iconic Malham Cove, to support people living with cancer.
  • Sat 27 Jun
  • £20-£25
  • 25% off
Skipton, North Yorkshire, UK

Mighty Hikes | Yorkshire Dales

Hike through the heart of the Yorkshire Dales, with its rolling green hills, drystone walls, and the iconic Malham Cove, to support people living with cancer.

  • Charity hike 2
  • Recycling
  • Fancy dress
  • Event village
  • Rural
  • Sustainability policy
  • Age 14 & over
A trekking challenge taking in moorland, ancient monuments, waterfalls, stunning coastal views and smuggler's coves in support of the brain cancer charity, brainstrust.
  • Sat 12 - Sun 13 Sep
  • £20-£30
  • 50% off
Whitby, North Yorkshire, UK

Follow the Seagulls | Yorkshire

A trekking challenge taking in moorland, ancient monuments, waterfalls, stunning coastal views and smuggler's coves in support of the brain cancer charity, brainstrust.

  • Charity walk 2
  • Dogs allowed at venue
  • Rural
  • Coast
  • Sustainability policy
  • Public transport links
  • Age 18 & over
  • Fri 3 - Mon 6 Apr
  • £299
Helmsley, North Yorkshire, UK

Cleveland Way Challenge

  • 4 days trekking
  • Fri 12 Jun
  • £45-£50
Settle, North Yorkshire, UK

Yorkshire 3 Peaks

  • 24.6 miles hiking + 9000 ft ascent

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