Stretching 100 miles (160 km) from Winchester in Hampshire to Eastbourne in East Sussex, the South Downs Way is one of England’s most iconic long-distance walking routes. This National Trail follows a high chalk ridge through the South Downs National Park, offering vast views over rolling farmland, wooded valleys, and the sparkling English Channel.
Walking holidays here blend the best of rural England — medieval villages, flint churches, ancient trackways — with some of the most dramatic coastal scenery in the country. The route is well-waymarked, easy to follow, and lined with welcoming places to stay, making it a favourite for self-guided walking breaks.
From Winchester’s medieval streets, the South Downs Way climbs onto chalk ridges lined with beech woods and wildflower meadows. Early stages pass ancient hillforts like Old Winchester Hill, Roman villas, and sweeping valleys dotted with sheep.
Crossing into West Sussex, the trail passes through the heart of the South Downs National Park, with open ridgelines offering uninterrupted views for miles. The path dips to historic towns like Amberley and Lewes, where cobbled lanes and country pubs make perfect overnight stops.
The final stretch is unforgettable: from the rolling downs above Alfriston, the trail reaches the white cliffs of the Seven Sisters and Beachy Head before descending into the seaside town of Eastbourne. Every stage combines rich history, beautiful landscapes, and a sense of open-air freedom.
Accommodation ranges from cosy B&Bs and country inns to boutique hotels and seaside stays. Popular bases include Winchester, Amberley, Arundel, Lewes, Alfriston, and Eastbourne. Campsites and hostels are also available for budget-friendly trips.
Booking ahead is essential, especially in summer when the South Downs Way attracts both walkers and cyclists. Many self-guided walking holiday companies offer luggage transfers so you can enjoy the trail without a heavy pack.
