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Challenge walks in Europe in May 2025

Find challenge walks near me in Europe 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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Click an event for full event details, location, route, sustainability, what's included and how to enter.

Walk, jog or run the stunning coastal paths of the Isle of Wight for a great charity cause, from the base camp at Chale, visiting historic Cowes and the iconic Needles en route.
  • Sat 3 - Sun 4 May 2025
  • 4 charities
  • Sat 3 - Sun 4 May 2025
  • 4 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge charity places

Walk, jog or run the stunning coastal paths of the Isle of Wight for a great charity cause, from the base camp at Chale, visiting historic Cowes and the iconic Needles en route.

  • Newcomers
  • Entertainment
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Age 14 & over
  • 1 day trail running
Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.
  • Sat 10 May 2025
  • £25
  • Sat 10 May 2025
  • £25
Cromer, Norfolk, UK

Mighty Hikes | Norfolk Coast | Marathon

Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.

  • Enter online
  • Fundraising required
  • Flat
  • Traffic free
  • Age 14 & over
  • 26.1 miles hiking + 300.33 m ascent
Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.
  • Sun 11 May 2025
  • £20
  • Sun 11 May 2025
  • £20
Cromer, Norfolk, UK

Mighty Hikes | Norfolk Coast | Half Marathon

Take on a challenge and join Macmillan at the Norfolk Coast Mighty Hike - where you'll explore beautiful beaches and picturesque fishing villages to support people living with cancer.

  • Enter online
  • Fundraising required
  • Flat
  • Traffic free
  • Age 14 & over
  • 14.3 miles hiking + 185.77 m 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 16 - Sun 18 May 2025
  • £350
  • Fri 16 - Sun 18 May 2025
  • £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.

  • Enter online
  • Fundraising required
  • Undulating
  • Hilly
  • Traffic free
  • Rural
  • Coast
  • Age 18 & over
  • 60 miles hiking
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
A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!
  • Sat 17 May 2025
  • £20
  • Sat 17 May 2025
  • £20
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight | One Day Challenge

A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!

  • Enter online
  • Fundraising required
  • Undulating
  • Age 18 & over
  • 25 miles walking
A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!
  • Sat 17 - Sun 18 May 2025
  • £30
  • Sat 17 - Sun 18 May 2025
  • £30
Cowes, Isle of Wight, UK

Follow the Seagulls | Isle of Wight | Two Day Challenge

A trekking challenge along the Isle of Wight Coastal Path with sea views, glades, tall ridges and wild walking in support of the brain cancer charity, brainstrust. You are in for a treat!

  • Enter online
  • Fundraising required
  • Undulating
  • Age 18 & over
  • 50 miles walking
Walk, jog or run along the fabulous UNESCO World Heritage coastline for charity, starting at the picturesque Corfe Castle, with a range of distances to suit all abilities and full support too.
  • Sat 17 - Sun 18 May 2025
  • 7 charities
  • Sat 17 - Sun 18 May 2025
  • 7 charities
Wareham, Dorset, UK

Jurassic Coast Ultra Challenge charity places

Walk, jog or run along the fabulous UNESCO World Heritage coastline for charity, starting at the picturesque Corfe Castle, with a range of distances to suit all abilities and full support too.

  • Newcomers
  • Entertainment
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Hilly
  • Event village
  • Age 14 & over
  • 1 day trail running
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
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
  • Sun 18 May 2025
  • £25
  • Sun 18 May 2025
  • £25
Epsom, Surrey, UK

Poppy Hike | Medium

Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.

  • Enter online
  • Fundraising required
  • Age 18 & over
  • 15 miles walking
Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.
  • Sun 18 May 2025
  • £25
  • Sun 18 May 2025
  • £25
Epsom, Surrey, UK

Poppy Hike | Long

Challenge yourself to a hike in the beautiful Surrey Hills and support the Armed Forces community, featuring Centenary Wood which commemorates the sacrifices made in WW1.

  • Enter online
  • Fundraising required
  • Age 18 & over
  • 21 miles walking
Walk, jog or run along the capital to coast route for charity, with a range of distance options available and superb support all the way, for all abilities and experience levels.
  • Sat 24 - Sun 25 May 2025
  • 7 charities
  • Sat 24 - Sun 25 May 2025
  • 7 charities
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge charity places

Walk, jog or run along the capital to coast route for charity, with a range of distance options available and superb support all the way, for all abilities and experience levels.

  • Entertainment
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Age 14 & over
  • 1 day trail running
Make a mountain of difference to people living with cancer. Beginning in the beautiful Greater Langdale valley in the Lake District, you will hike to the top of England's highest mountain - Scafell.
  • Sat 31 May 2025
  • £45-£120
  • Sat 31 May 2025
  • £45-£120
Ambleside, Cumbria, UK

Defeat the Peak | Scafell Pike by Day Challenge

Make a mountain of difference to people living with cancer. Beginning in the beautiful Greater Langdale valley in the Lake District, you will hike to the top of England's highest mountain - Scafell.

  • Enter online
  • Fundraising required
  • Mountainous
  • Traffic free
  • Rural
  • Mountains
  • Sustainability policy
  • Age 14 & over
  • 12 hrs hiking + 1500 m ascent
  • Sat 17 May 2025
Keswick, Cumbria, UK

Keswick Mountain Festival 3 Peaks

  • 18 miles hiking + 1050 m ascent
  • Sun 18 May 2025
Keswick, Cumbria, UK

Keswick Mountain Festival 8 Peaks

  • 18 miles hiking + 1350 m ascent

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