15 Challenge walks in Scotland

Find challenge walks in and around Scotland for 2024/2025 - 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 a challenging 23 mile route.
  • Sun 28 Apr
  • £20
  • 2 charities
Glasgow, Glasgow City, UK

The Kiltwalk Glasgow | Mighty Stride

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.

  • 22.6 miles
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.
  • Sun 28 Apr
  • £20
  • 1 charity
Clydebank, West Dunbartonshire, UK

The Kiltwalk Glasgow | Big Stroll

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.

  • 14.2 miles
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 18 May
  • £30
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.

  • 26.2 miles hiking + 2456 ft ascent
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 18 May
  • £25
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.

  • 13.8 miles hiking + 1298 ft ascent
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in Aberdeen this year over a challenging 18 mile route.
  • Sun 2 Jun
  • £20
  • 1 charity
Banchory, Aberdeenshire, UK

The Kiltwalk Aberdeen | Mighty Stride

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

  • 17.8 miles
Explore more for little paws! Cats aren't the only cool climbers - us humans are pretty good too! Conquer Scotland's highest peak to raise vital funds for our feline friends.
  • Sat 22 Jun
  • £25-£55
Fort William, Highland, UK

Ben Nevis Climb

Explore more for little paws! Cats aren't the only cool climbers - us humans are pretty good too! Conquer Scotland's highest peak to raise vital funds for our feline friends.

  • 1 day hiking + 1344 m ascent
Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in the City of Discovery over a challenging 20 mile route.
  • Sun 11 Aug
  • £20
  • 8 charities
Dundee, Dundee City, UK

The Kiltwalk Dundee | Mighty Stride

Get ready, Kiltwalkers! Experience the banter, fun, bagpipes, support and sheer emotion in the City of Discovery over a challenging 20 mile route.

  • 21.5 miles
A tough urban hike on hidden city routes with 7 viewpoints! Follow historic waterways, forgotten railways, castles, palaces and climb to the summit of Arthurs Seat - an extinct volcano!
  • Sat 24 Aug
  • £45
Edinburgh, Edinburgh, UK

Edinburgh 7 Summits Challenge

A tough urban hike on hidden city routes with 7 viewpoints! Follow historic waterways, forgotten railways, castles, palaces and climb to the summit of Arthurs Seat - an extinct volcano!

  • 35 km hiking + 900 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 31 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.

  • 25.2 miles hiking + 896 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 31 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.

  • 15.3 miles hiking + 524 m ascent
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 15 Sep
  • £20
  • 8 charities
Edinburgh, Edinburgh, UK

The Kiltwalk Edinburgh | Mighty Stride

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

  • 21 miles
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 15 Sep
  • £20
  • 8 charities
Musselburgh, East Lothian, UK

The Kiltwalk Edinburgh | Big Stroll

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

  • 11 miles
MS Walk Glasgow is back for another successful year and takes in some of the city’s iconic landmarks and culture. Sign up today and walk, roll or stroll to stop MS.
  • Sat 28 Sep
  • FREE-£15
Glasgow, Glasgow City, UK

MS Walk Glasgow | 20K

MS Walk Glasgow is back for another successful year and takes in some of the city’s iconic landmarks and culture. Sign up today and walk, roll or stroll to stop MS.

  • 20 km
  • Sat 24 Aug
  • £200-£400
Melrose, Scottish Borders, UK

Run the Borders | Walking Challenge (Teams of 4)

Run the Borders is Breaking Strain's newest trail race.

  • 36 hrs
  • Thu 3 Oct
  • £450
Fort William, Highland, UK

Conquer the UK Three Peaks | Hike for Homelessness

Your next adventure could be the start the start of someone’s journey out of homelessness. Take on the Three Peaks Challenge.

  • 3 days hiking

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