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Challenge walks in Scotland

Find challenge walks near me in Scotland for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.

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Get ready, Kiltwalkers! Experience the banter, fun, pipes, blethering, support and sheer emotion in Scotland's second city this year on an achievable 14 mile route.
  • Sat 26 Apr
  • 4 charities
  • Sat 26 Apr
  • 4 charities
Clydebank, West Dunbartonshire, UK

The Kiltwalk Glasgow | Big Stroll charity places

Get ready, Kiltwalkers! Experience the banter, fun, pipes, blethering, support and sheer emotion in Scotland's second city this year on an achievable 14 mile route.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 10 & over
  • 14.2 miles walking
Get ready, Kiltwalkers! Experience the banter, fun, pipes, blethering, support and sheer emotion in Scotland's second city this year on a challenging 23 mile route.
  • Sun 27 Apr
  • 4 charities
  • Sun 27 Apr
  • 4 charities
Glasgow, Glasgow City, UK

The Kiltwalk Glasgow | Mighty Stride charity places

Get ready, Kiltwalkers! Experience the banter, fun, pipes, blethering, support and sheer emotion in Scotland's second city this year on a challenging 23 mile route.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 22.6 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
  • £25
  • Sat 17 May
  • £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
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
  • 6 charities
  • Sat 17 May
  • 6 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
  • £20
  • Sat 17 May
  • £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
Get ready to explore one of Scotland's oldest and most iconic resorts, nestled in the heart of Perthshire, experiencing breathtaking countryside, with rolling hills, lush woodlands and scenic trails.
  • Sat 31 May
  • £25
  • Sat 31 May
  • £25
Crieff, Perth and Kinross, UK

Pink Ribbon Walk Scotland | Crieff Hydro | 20 Mile

Get ready to explore one of Scotland's oldest and most iconic resorts, nestled in the heart of Perthshire, experiencing breathtaking countryside, with rolling hills, lush woodlands and scenic trails.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 20 miles walking
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Aberdeen this year over a challenging 18 mile route.
  • Sun 1 Jun
  • 4 charities
  • Sun 1 Jun
  • 4 charities
Banchory, Aberdeenshire, UK

The Kiltwalk Aberdeen | Mighty Stride charity places

Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Aberdeen this year over a challenging 18 mile route.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 17.8 miles walking
Make a mountain of difference to people living with cancer. Beginning in the beautiful Glen Nevis in the Scottish Highlands, this spectacular challenge will see you reach the top for beautiful views!
  • Sat 7 Jun
  • £45-£120
  • Sat 7 Jun
  • £45-£120
Fort William, Highland, UK

Defeat the Peak | Ben Nevis by Day Challenge

Make a mountain of difference to people living with cancer. Beginning in the beautiful Glen Nevis in the Scottish Highlands, this spectacular challenge will see you reach the top for beautiful views!

  • Enter online
  • Fundraising required
  • Mountainous
  • Traffic free
  • Rural
  • Mountains
  • Sustainability policy
  • Age 14 & over
  • 8 hrs hiking + 4413 ft ascent
Challenge yourself and support Mind at the same time as you tackle this renowned mountain adventure to help empower those experiencing a mental health problem.
  • Fri 20 - Sun 22 Jun
  • £95
  • Fri 20 - Sun 22 Jun
  • £95
Fort William, Highland, UK

Three Peaks Challenge

Challenge yourself and support Mind at the same time as you tackle this renowned mountain adventure to help empower those experiencing a mental health problem.

  • Recycling
  • Plastic bottle free
  • Enter online
  • Fundraising required
  • Mountainous
  • Rural
  • Mountains
  • Sustainability policy
  • Public transport links
  • Age 18 & over
  • 24 hrs hiking
Starting alongside those taking on the full route, runners and walkers alike will feel the buzz of the startline before running past all four of the route's ruined abbeys to finish at Jedburgh.
  • Sat 23 Aug
  • £38-£46
  • Sat 23 Aug
  • £38-£46
Melrose, Scottish Borders, UK

Run the Borders | 50K Ultra

Starting alongside those taking on the full route, runners and walkers alike will feel the buzz of the startline before running past all four of the route's ruined abbeys to finish at Jedburgh.

  • Chip timing
  • Enter online
  • GPS tracking
  • Age 18 & over
  • 50 km trail running
Take on a challenge and join Macmillan at the Rob Roy Mighty Hike, where you'll explore the Rob Roy Way through the wild and beautiful Trossachs National Park to support people living with cancer.
  • Sat 30 Aug
  • £25
  • Sat 30 Aug
  • £25
Callander, Stirling, UK

Mighty Hikes | Rob Roy | Marathon

Take on a challenge and join Macmillan at the Rob Roy Mighty Hike, where you'll explore the Rob Roy Way through the wild and beautiful Trossachs National Park to support people living with cancer.

  • Enter online
  • Fundraising required
  • Hilly
  • Age 14 & over
  • 25.2 miles hiking + 870.37 m ascent
Take on a challenge and join Macmillan at the Rob Roy Mighty Hike, where you'll explore the Rob Roy Way through the wild and beautiful Trossachs National Park to support people living with cancer.
  • Sat 30 Aug
  • £20
  • Sat 30 Aug
  • £20
Callander, Stirling, UK

Mighty Hikes | Rob Roy | Half Marathon

Take on a challenge and join Macmillan at the Rob Roy Mighty Hike, where you'll explore the Rob Roy Way through the wild and beautiful Trossachs National Park to support people living with cancer.

  • Enter online
  • Fundraising required
  • Hilly
  • Age 14 & over
  • 15.3 miles hiking + 530.47 m ascent
A trekking challenge with tranquil forests, historic castles, quaint fishing villages and beautiful beaches to support brainstrust, the brain cancer charity.
  • Sat 13 Sep
  • £20
  • Sat 13 Sep
  • £20
Newburgh, Fife, UK

Follow the Seagulls | Scotland | One Day Challenge

A trekking challenge with tranquil forests, historic castles, quaint fishing villages and beautiful beaches to support brainstrust, the brain cancer charity.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 18 & over
  • 26 miles walking
A trekking challenge with tranquil forests, historic castles, quaint fishing villages and beautiful beaches to support brainstrust, the brain cancer charity.
  • Sat 13 - Sun 14 Sep
  • £30
  • Sat 13 - Sun 14 Sep
  • £30
Newburgh, Fife, UK

Follow the Seagulls | Scotland | Two Day Challenge

A trekking challenge with tranquil forests, historic castles, quaint fishing villages and beautiful beaches to support brainstrust, the brain cancer charity.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 18 & over
  • 50 miles walking
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Scotland's capital this year over a challenging 21 mile route.
  • Sun 14 Sep
  • 6 charities
  • Sun 14 Sep
  • 6 charities
Edinburgh, UK

The Kiltwalk Edinburgh | Mighty Stride charity places

Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Scotland's capital this year over a challenging 21 mile route.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 13 & over
  • 21 miles walking
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Scotland's capital this year over an achievable 11 mile route.
  • Sun 14 Sep
  • 5 charities
  • Sun 14 Sep
  • 5 charities
Musselburgh, East Lothian, UK

The Kiltwalk Edinburgh | Big Stroll charity places

Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Scotland's capital this year over an achievable 11 mile route.

  • Enter online
  • Fundraising required
  • Undulating
  • Age 10 & over
  • 11 miles walking
  • Sat 7 Jun
Kinross, Perth and Kinross, UK

The Cateran Yomp | 54 Mile Yomp

  • 54 miles walking
  • Sat 7 Jun
Kinross, Perth and Kinross, UK

The Cateran Yomp | 36 Mile Yomp

  • 36 miles walking
  • Sat 7 Jun
Kinross, Perth and Kinross, UK

The Cateran Yomp | 22 Mile Yomp

  • 22 miles walking
  • Thu 19 - Sun 22 Jun
Glasgow, East Dunbartonshire, UK

West Highland Way Challenge

  • 4 days trekking

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