Classic Trails in Scotland

The country of Scotland, with its magnificent mountains, remote glens, sparkling lochs, rugged coastline, magical islands and rich wildlife, has plenty to attract walkers of all interests. The scenery in Scotland is renowned worldwide for its breath-taking beauty, with far-reaching panoramas just waiting to be discovered. Brimming with a hearty mixture of industrial and cultural history, Scotland has plenty to offer those keen to explore the country's past.

Our choice of Classic Trails in Scotland aim to showcase the many highlights and hidden gems scattered around this glorious country; select a trail below to learn more.

Refine further

All Dog-Friendly
Great Glen Way

Great Glen Way
3 to 8 nights
22-77 miles
Moderate+
From £390 per person
A walk through Scotland's Great Glen along the impressive Caledonian Canal. Find Out More
Rob Roy Way

Rob Roy Way
3 to 9 nights
23-78 miles
Easy / Moderate+
From £355 per person
A walk from Loch Lomond, through the Trossachs National Park and the Highlands of Perthshire. Find Out More
Speyside Way

Speyside Way
3 to 11 nights
27-101 miles
Moderate+
From £385 per person
A self-guided walking holiday from Buckie to Newtonmore, following the course of the spectacular River Spey Find Out More
St Cuthbert's Way

St Cuthbert's Way
5 to 8 nights
64-69 miles
Moderate+
Dog friendly
From £590 per person
A self-guided walking holiday celebrating the many historic sites associated with St Cuthbert. Find Out More
West Highland Way

West Highland Way
4 to 10 nights
47-95 miles
Moderate+
From £505 per person
A walking holiday along the iconic long-distance route between Milngavie and Fort William. Find Out More
Contours Walking Holidays Contours Cycling Holidays Contours Trail Running Holidays

Please be aware that this website uses cookies to give you the best possible experience. We value your privacy and treat your data with care. Learn more.

For more information, please refer to our privacy policy.

Strictly necessary cookies which are essential for navigating a website and using its features and functionalities. These temporary 'session' cookies are required for basic services such as logging in or making a booking.

Marketing cookies which are used to monitor our marketing & advertising efforts, enabling us to personalise content and enhance results.

Analytics cookies track website usage data, including traffic numbers, page views, and user interactions. This information helps us improve website performance and understand user behavior.

User experience cookies enhance the browsing experience by enabling features like heatmapping and chat functionalities, allowing us to better understand user behavior and improve website usability.