South Downs Way - Winchester to Eastbourne

The South Downs Way is a tranquil island in the busy South East running entirely within the South Downs National Park. You can feel a million miles from the hustle and bustle of modern life, but only be a few minutes from civilisation.

The 100 mile (160 km) long South Downs Way National Trail follows old routes and droveways along the chalk escarpment and ridges of the South Downs. The route provides the visitor with the opportunity “to get away from it all” without having to travel too far in this busy part of England.

The Trail follows the chalk ridge just to the north of the popular seaside towns on the Sussex and Hampshire coast. At intervals the hilly downlands are broken by “wind gaps” or river valleys, mixing the ridge walking with some meandering visits to beautiful rivers such at the Cuckmere, Arun, Ouse and Meon with their associated villages. Most of the route is ancient, made up out of the old droving roads that took animals and goods between the market towns of the region. There are many historical features, including a couple of remaining round towered Saxon churches, ancient “Dew Ponds” providing water on the high Downs for cattle, cross dykes and tumulus burial sites, Bronze Age hill forts and rings.

The weather on average is some of the best you could find in the British Isles, and soft boots or even trekking shoes are generally advised, as the surfaces are often –but not universally – dry and firm. The tour is accessible easily from London and the Southeast by railway.

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 Sherpa Expeditions who place great emphasis on researching, planning and crafting innovative itineraries to ensure you get the very best experience out of your trip.

The detailed route notes and maps provided share hidden gems and secret spots that will immerse you deep in the natural beauty and intriguing cultures of the landscapes you explore. At the end of each day, Sherpa want to make sure that you have a great night’s rest. Your accommodation is carefully selected to ensure it best reflects the character of the destination you are visiting and offers the location, service and quality standards you expect.

When you book, your trip will be fully organised by a dedicated member of Sherpa’s in-house team, so you will always know who you are dealing with.

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 10 day tour including 9 nights accommodation and 8 days of walking. The tour starts in Winchester, a cathedral city on the edge of the South Downs ending 160 kilometres (100 miles) later in the coastal town of Eastbourne.

Day 1 - Arrive Winchester

Make your own way to Winchester. You may wish to spend some extra time to explore this gem of a town – the ancient capital of England and the Kingdom of Wessex before that. The cathedral has the longest nave in Britain and there is a beautiful walk down through the water meadows to St. Cross. Where a “Dole” of bread and Ale can still be obtained from the monastic buildings.

Day 2 - Winchester to East Meon

The route ascends out from Winchester, old England’s Saxon capital, onto the downs at Chilcomb – an old manorial parish. Until the Meon Valley the scenery is undulating and agricultural, a warm up without being dramatic. You reach the attractive Meon valley via Beacon Hill with its rare spring and summer plant life. The Hampshire Downs then open up and roll on as you pass field after field. At around lunchtime, the necklace of Meon Valley villages: Exton, Corhampton and Meonstoke are all within a mile of each other and are beautiful places to river watch and to quaff beer by as the Meon River is a real gem! The River Meon is a very healthy, clean chalk stream. The climb from here up towards Old Winchester Hill is long and steep in its latter stages, so take your time. To start with, ascend beside a beautiful clear chalk stream in which you may see Brown Trout gliding about. The site is a National Nature Reserve and Iron Age fortress from where the Isle of Wight can be seen on a clear day.

26 km/16 miles

Day 7 - Pyecombe to Rodmell

Ascend out of Pyecombe near Clayton, passing lark filled skies and the white “Jack and Jill“ Clayton windmills greet you. Today, following mainly grassy tracks, you go over the highest point directly on the route at Ditchling Beacon 248 m. You may find an ice cream van up here in summer. There are no real difficulties today, although the climb up from the road is pretty steep. The South Downs Way undulates between large fields and long slopes, until you reach the River Ouse gap near Rodmell. Before the trail descends to Southease and into Rodmell. Fans of the Bloomsbury group of Bohemian artists, will be delighted to know that Rodmell Village has a pub and the “Monk’s House” is where Virginia Woolf used to live.

22.5 km/14 miles

Day 8 - Rodmell to Alfriston

Today’s walk is quite brief, so there is plenty of time to enjoy a late breakfast and spend extra time in Rodmell. Today you cross the valley of the River Ouse and steeply ascend steeply back up the South Downs to the Firle Beacon 217 m and another great viewpoint. As you do have plenty of time, you may consider coming off the hills to visit the villages of west Firle, Alciston and Berwick. These tiny villages all have associations with the Bloomsbury Group and Berwick Church has some interesting paintings.

15.2 km/9.5 miles

Day 9 - Alfriston to Eastbourne

From Alfriston follow the meandering aquamarine elegance of the Cuckmere River firstly along the river bank and then by the village of Litlington, the path then takes you up onto the downs above the river, passing points where you can appreciate its meanders. At Cliff End you turn to the East and follow the roller-coaster trail over The Seven Sisters, a series of iconic chalk cliffs to Beachy Head with its famous lighthouse. From here the trail continues on beside the sea before descending steeply off the hills via Holywell. Finally enter the outskirts of Eastbourne and walk along the Victorian Promenade to the Victorian Pier which makes an appropriate place to end the South Downs Way. You may wish to book another night to relax and maybe take a dip in the sea.

17 km/10.5 miles

Day 10 - Arrangements end after breakfast

Your trip concludes.


Nine nights bed & breakfast accommodation is provided in guesthouses and country inns on a twin share basis with ensuite facilities where available.


Bus & Rail

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.



Ferry & Air

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.

Itinerary Map

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