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Challenge walks in May 2026

Find challenge walks near me 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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Starting in Cromer, this scenic coastal hike follows beautiful beaches and picturesque villages along the coast, combining breathtaking views with the chance to support people living with cancer.
  • Sat 9 - Sun 10 May 2026
  • £20-£25
  • 30% off
Cromer, Norfolk, UK

Mighty Hikes | Norfolk Coast

Starting in Cromer, this scenic coastal hike follows beautiful beaches and picturesque villages along the coast, combining breathtaking views with the chance to support people living with cancer.

30% off with discount code

  • Recycling
  • Fancy dress
  • Event village
  • Rural
  • Coast
  • Sustainability policy
  • Public transport links
  • Age 14 & over
  • Hike 2
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
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 UK's top outdoor sports festival! Incredible entertainment, sports events, speakers, live music, activities, brand expo, bars, food, drink and much more.
  • Fri 15 - Sun 17 May 2026
  • £30
  • Early bird
Keswick, Cumbria, UK

Keswick Mountain Festival

The UK's top outdoor sports festival! Incredible entertainment, sports events, speakers, live music, activities, brand expo, bars, food, drink and much more.

Early bird on now

  • Families
  • Venue accessible
  • Newcomers
  • Dogs allowed at venue
  • Entertainment
  • Music
  • Enter online
  • Event village
  • Event expo
  • Park
  • Rural
  • Mountains
  • Sustainability policy
  • All ages
  • 5K run 2
  • 10K run
  • Half marathon
  • 50K ultra run
  • Fell run
  • + 12 more races
  • Sat 16 - Sun 17 May 2026
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight

  • Charity walk 2
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
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
  • Fri 15 - Sun 17 May 2026
Westward Ho!, Devon, UK

Incredible Hike

  • 60 miles hiking

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