Walking Holidays and Stays in South East England

Chalk Hills, Beech Woods, and Clifftop Paths

Where long ridgelines, quiet forests, and coastlines tell the story of old England.

South East England offers a blend of natural calm and cultural depth. This is a region of rolling downs, ancient woodlands, and weathered shorelines, shaped by centuries of footsteps. Footpaths pass through farm fields, cathedral towns, and coastal villages — landscapes where tradition, ecology, and gentle beauty meet.

From the high tracks of the South Downs to the quiet charm of the High Weald and the iconic cliffs of the Seven Sisters, this is walking country for those seeking connection, stillness, and story.

Where to Walk

South Downs Way

‍This 100-mile National Trail runs from Winchester to Eastbourne, tracing a chalk ridgeline through Hampshire and East Sussex. Walkers pass open fields, beech hangers, and market towns like Petersfield and Lewes, with long views over the Weald and out to sea.

North Downs Way

‍A ridge trail running from Farnham to Dover, crossing both the Surrey Hills and Kent Downs AONBs. Highlights include Canterbury Cathedral, Box Hill, and peaceful stretches through woodland, pasture, and historic villages.

High Weald & Sussex Ridges

‍This inland area is full of short, scenic walks through wooded valleys, sandstone ridges, and ancient farmscapes. Base yourself in Rye, Tenterden, or Lewes to explore trails wrapped in rural charm, hedgerows, and heritage.

The Coast & Seven Sisters

‍The Seven Sisters cliffs between Seaford and Eastbourne offer one of England’s most dramatic coastal walks. Further east, explore the Kent coast — with saltmarshes, shingle beaches, and villages like Whitstable, Deal, and Sandwich.

Highlights

• Long-distance walks along the South Downs Way and North Downs Way
• Forest trails and ridge walks near Rye, Tenterden, and Lewes
• Iconic clifftop routes above the Seven Sisters, and saltmarsh paths along the Kent coast
• A region of gentle gradients, wide skies, and historic charm — perfect for self-guided walking holidays and slow travel

South East England rewards quiet exploration. Its trails weave through layers of story and landscape — made for those who want to walk a little slower, and see a little deeper.