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Challenge walks in May 2026

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

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The finish line is unique to you: 24 hours after the mass start, the race shall stop and the Solo Runners and Teams furthest South on the National Trail, shall be declared winners.
  • Sat 9 - Sun 10 May 2026
  • £95.50-£155.50
  • Sat 9 - Sun 10 May 2026
  • £95.50-£155.50
Prestatyn, Clwyd, UK

24 Hours South | The Offa's Dyke Ultra

The finish line is unique to you: 24 hours after the mass start, the race shall stop and the Solo Runners and Teams furthest South on the National Trail, shall be declared winners.

  • Newcomers
  • Chip timing
  • Enter online
  • GPS tracking
  • Event village
  • Rural
  • Age 18 & over
  • 24 hrs trail running + 8561 ft ascent
The ultimate coast path challenge! Walk 60 miles of the South West Coast Path over 3 days and take in the breathtaking sights and soak up the camaraderie for Children’s Hospice South West.
  • Fri 15 - Sun 17 May 2026
  • £350
  • Fri 15 - Sun 17 May 2026
  • £350
Westward Ho!, Devon, UK

Incredible Hike

The ultimate coast path challenge! Walk 60 miles of the South West Coast Path over 3 days and take in the breathtaking sights and soak up the camaraderie for Children’s Hospice South West.

  • Fundraising required
  • Undulating
  • Hilly
  • Traffic free
  • Rural
  • Coast
  • Age 18 & over
  • 60 miles hiking
A mid-level, circular hike over the three peaks surrounding Derwentwater Catbells, Walla Crag and Latrigg. Includes Full Weekend Festival Ticket in the price!
  • Sat 16 May 2026
  • £30-£55
  • Sat 16 May 2026
  • £30-£55
Keswick, Cumbria, UK

Keswick Mountain Festival 3 Peaks

A mid-level, circular hike over the three peaks surrounding Derwentwater Catbells, Walla Crag and Latrigg. Includes Full Weekend Festival Ticket in the price!

  • Families
  • Newcomers
  • Music
  • Chip timing
  • Mountainous
  • Event village
  • Age 12 & over
  • 18 miles hiking + 1050 m ascent
A high-level horseshoe walk on varied terrain around the stunning fells surrounding Derwentwater and the Borrowdale Valley for experienced hikers. Includes Full Weekend Festival Ticket in the price!
  • Sun 17 May 2026
  • £65
  • Sun 17 May 2026
  • £65
Keswick, Cumbria, UK

Keswick Mountain Festival 8 Peaks

A high-level horseshoe walk on varied terrain around the stunning fells surrounding Derwentwater and the Borrowdale Valley for experienced hikers. Includes Full Weekend Festival Ticket in the price!

  • Newcomers
  • Music
  • Chip timing
  • Mountainous
  • Event village
  • Age 18 & over
  • 18 miles hiking + 1350 m ascent
The 10km Nordic Walk takes a scenic route through some classic Lake District Landscapes, including the shores of Grasmere and Rydal, as you propel yourself along with your poles.
  • Sat 30 May 2026
  • £30
  • Sat 30 May 2026
  • £30
Ambleside, Cumbria, UK

Lake District Running Festival | Grasmere Gallop Nordic Walking Challenge

The 10km Nordic Walk takes a scenic route through some classic Lake District Landscapes, including the shores of Grasmere and Rydal, as you propel yourself along with your poles.

  • Undulating
  • Age 15 & over
  • 10 km walking + 160 m ascent

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