South Downs Way - Winchester to Eastbourne

This 9 day organised walk along the South Downs Way allows you to enjoy the best of the British Countryside and traditional rural villages whilst still being close to civilisation.

This is an organised nine day walk along the full 100 mile length of the South Downs Way, one of England’s finest National Trails. It takes place every June and is now in it’s 43rd year! It has been enjoyed by hundreds of people  from all over the world. It is by tradition, a supported rather than a guided walk, with everyone free to walk at their own pace each day. However, our team of experienced leaders walk the South Downs Way with you and you can rest assured that there will always be knowledgeable people nearby to help you with directions, first aid or just a friendly smile.


Tour Overview

The icons below highlight the distance, difficulty and theme of this itinerary.








Wildlife. Food and Drink

Landscape Type

Rolling Countryside, Connecting towns and villages

A journey along the South Downs

Every step of the journey has been carefully planned to help you make the most of your walking adventure.

Tour Details

This itinerary has been created by Footprints of Sussex who are local experts in the South Downs. Footprints have been organising this annual walk for over 40 years and will ensure you get the very best experience of the South Downs.


To find out more about this itinerary and make an enquiry or a booking, click on the Enquire Now button at the top of the page. The Save to My Rucksack button allows you to save itineraries to view later, or to download them as a PDF.


This is a 9 day lead walking tour including, knowledgeable expert walk leaders and pick up and drop off coach travel to and from the start and finish of each days walk. This package does not include accommodation. The tour starts in Winchester, the ancient capital of Wessex on the edge of the South Downs ending 160 kilometres (100 miles) later at the dramatic coastal cliffs of Eastbourne.

On this first day you will get dropped off by coach at Winchester and walk to Exton Village. here you can enjoy some refreshment at the Shoe Inn whilst waiting for your return coach.

After being dropped of back at Exton you’ll walk to Queen Elizabeth Country Park. There is refreshments available at the Sustainability centre and at the end of the day at QECP.


Today you’ll walk from QECP to Cocking. The Way takes you though forest, over Beacon Hill and passed the Devil’s Jumps, ancient Bronze age burial mounds.

Walking from Cocking to Amberley you’ll pass some stunning wildflower meadows and enjoy extensive views.

19.3 km/12 miles

You’re now more than halfway! There is a steep climb up above Amberley, but the view makes it worth it.

17.7 km/11 miles

Todays walk from Steyning to Pyecombe takes in the iconic Fulking escarpment and the Devil’s Dyke, Britain’s deepest dry valley.

16 km/10 miles

Walking from Pyecombe to Southease you’ll pass Jack & Jill Windmills and walk over Ditchling Beacon, the highest point in the East Sussex part of the National Park.

22.5 km/14 miles

Walking from Southease to Alfriston you’ll enjoy fine examples of flower rich chalk grassland and expansive open views. Alfriston is a small historic Downland village famous for having the National Trust’s first property, Alfriston Clergy House.

15.2 km/9.5 miles

The most iconic section of the South Downs Way. You can either walk along the towering chalk cliffs of the Seven Sisters and Beachy Head or opt for the inland route passing over the ancient chalk figure of the Long Man of Wilmington.

17 km/10.5 miles


It’s easy to get to the South Downs Way, it has good public transport links which get better the further east you go. 
There are main line trains and long distance coaches to both Winchester and Eastbourne as well as several places in between. Allow around 60 – 90 minutes from London.

You can plan your journey using Traveline.



Ferries to Newhaven and Portsmouth, and the London Airports (especially Gatwick) are handy for overseas visitors.


Anyone who is reasonably fit can walk the South Downs Way. The tour is graded as ‘Moderate’  with straight forward undulating walking, often on farm tracks and chalk down. Each day ranges from 9.5 miles / 15.2km to 18 miles / 29 km. From 4 to 7 hours walking.

The Trail can be enjoyed at any time of the year. However it does get busier during school holidays and on weekends between May and September you should expect to come across larger organised events.

Food & Drink

You’ll be spoiled for choice with so much great local food and drink on offer. You will pass through many small villages and towns with good pubs and cafes.

Maps, Guidebooks and Merchandise

The official guidebook and map for the Trail are available from the National Trails Shop along with a wide range of gifts and other merchandise.

Itinerary Map

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Points of interest




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Points of interest


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