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Challenge walks in UK in May 2026

Find challenge walks in UK 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
  • £20-£25
  • 25% 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.

25% off with discount code

  • Recycling
  • Fancy dress
  • Event village
  • Rural
  • Coast
  • Sustainability policy
  • Public transport links
  • Age 14 & over
  • Charity 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
  • £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.

  • Beginner-friendly
  • 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
  • £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
  • Beginner-friendly
  • 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
  • + 14 more races
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

  • Rural
  • Coast
  • Sustainability policy
  • Public transport links
  • Age 18 & over
  • Charity walk 2
Escape to nature and take on a Big Hike in the Trossachs. You’ll explore stunning lochs, waterfalls, and forests whilst supporting life-saving research.
  • Sat 16 May
  • £20-£25
  • 30% off
Callander, Stirling, UK

Big Hike | The Trossachs

Escape to nature and take on a Big Hike in the Trossachs. You’ll explore stunning lochs, waterfalls, and forests whilst supporting life-saving research.

30% off in January

  • Families
  • Recycling
  • Beginner-friendly
  • Fancy dress
  • Event village
  • Rural
  • Sustainability policy
  • Public transport links
  • Age 12 & over
  • Hike 3
Experience Snowdonia’s awe-inspiring landscapes alongside an incredible team of Breakthrough T1D supporters, uniting every step to create a brighter future for people living with type 1 diabetes.
  • Sat 23 May
  • £15-£30
Caernarfon, Gwynedd, UK

Snowdon Trek

Experience Snowdonia’s awe-inspiring landscapes alongside an incredible team of Breakthrough T1D supporters, uniting every step to create a brighter future for people living with type 1 diabetes.

  • Families
  • Beginner-friendly
  • Enter online
  • Fundraising required
  • Mountainous
  • Event village
  • Mountains
  • Age 11 & over
  • 12 miles hiking
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
  • £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
Westward Ho!, Devon, UK

Incredible Hike

  • 60 miles hiking
  • Sat 16 - Sun 17 May
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge

  • Trail run 2
  • 50K ultra run 2
  • 100K ultra run 2
  • Marathon
  • Ultra run
  • + 1 more race
  • Fri 22 - Mon 25 May
Glasgow, East Dunbartonshire, UK

West Highland Way Challenge

  • 4 days trekking

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