Classic Trails in the South of England

The South of England is noted for its great variety, from rocky coastlines and sandy beaches to wild expanses and rolling green hills, and everything in between. The area is home to countless Areas of Outstanding Natural Beauty, National Parks, World Heritage Sites, Sites of Special Scientific Interest, rare wildlife nature reserves and unique insights into the country's cultural, industrial and territorial history.

Our Classic Trails in the South of England showcase some of the very best walking paths in this region. Select a trail below to learn more.

Refine further

All Dog-Friendly
Cotswold Way

Cotswold Way
4 to 16 nights
26-102 miles
Easy / Moderate+
Dog friendly
From £500 per person
A magnificent trail showcasing the world-famous Cotswolds Area of Outstanding Natural Beauty. Find Out More
Peddars Way & Norfolk Coast Path

Peddars Way & Norfolk Coast Path
3 to 18 nights
17-141 miles
Easy to Demanding
Dog friendly
From £420 per person
A walk through the ancient breckland of the Peddars Way Roman road and along the beautiful east coast. Find Out More
North Downs Way

North Downs Way
3 to 14 nights
19-137 miles
Moderate+
From £415 per person
A self-guided walking holiday through the Surrey Hills and Kent Downs, from Farnham to Dover. Find Out More
South Downs Way

South Downs Way
3 to 11 nights
22-102 miles
Moderate+
Dog friendly
From £425 per person
A walk along the chalk downs of Hampshire and Sussex, from Winchester to Eastbourne. Find Out More
South West Coast Path

South West Coast Path
3 to 12 nights
630 miles
Easy+
Dog friendly
From £355 per person
An epic walk along the coastline of Cornwall, Devon, Somerset and Dorset. Find Out More
Thames Path

Thames Path
5 to 23 nights
88-192 miles
Easy / Moderate+
Dog friendly
From £730 per person
A scenic walk following the development of the River Thames from a stream in Kemble all the way to the sea. Find Out More
The Ridgeway

The Ridgeway
4 to 12 nights
45-93 miles
Easy / Moderate+
Dog friendly
From £515 per person
A walk along Britain's oldest road through the ancient landscapes of the Wessex Downs and the Chiltern Hills. 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.