May marks National Walking Month, and what better way to celebrate than by lacing up your boots and exploring the beautiful countryside of the South East on foot? Whether you’re a seasoned hiker or just looking to stretch your legs in the great outdoors, Kent and Sussex are crisscrossed with trails that promise fresh air and incredible views.
Better still, many of our holiday homes sit right on the doorstep of some of the county’s most scenic routes. From coastal rambles to woodland wanders and vineyard valleys, here are a few of our favourite walking spots – each paired with the perfect place to rest your feet at the end of the day.
North Downs Way (Wye to Chilham)
Stay: The Hayloft, near Wye
Embark on a captivating section of the North Downs Way between Wye and Chilham – this 6-mile stretch winds through lush valleys and ancient woodlands, culminating in a picturesque village. After exploring the historic square, you can catch a train back to Wye, making it a convenient linear walk.
For something more challenging, guests at The Hayloft (sleeps 8) can hike a rewarding door-to-door circular, passing the Wye Downs and the intriguing Devil’s Kneading Trough – a natural amphitheatre carved into the chalk hills – before they reach the North Downs Way. Back at the property, you can rest sore legs in the outdoor hot tub, which benefits from unparalleled panoramic views of the Kentish countryside, offering a blissful end to a beautiful walk.
High Weald AONB
Stay: Cart Lodge & Dairy Barn, Blackham
Nestled deep in the High Weald AONB, these two properties offer classic English countryside at its best – think mysterious ancient woodlands strewn with bluebells, fern-clad streams, knobbly orchards, and sleepy, sunken lanes. Whether you opt for a 2-mile morning loop or a longer ramble, these properties offer a brilliant base for soaking up the rural charm of the Kent-Sussex border, with both homes featuring doorstep access to a network of enchanting trails.
North Downs Way (Charing to Wye)
Stay: Dormestone House, near Wye
This segment of the North Downs Way offers a tranquil 7.5-mile journey from Charing to Wye. The path meanders through chalky grasslands, offering panoramic views and a sense of serenity. Quiet lanes juxtapose the walk’s wide, open spaces, making it a perfect choice for those seeking some immersion in nature. Upon reaching Wye, enjoy a hearty meal at The Tickled Trout, or – if you can’t wait that long – stock up on local produce at Perry Court Farm Shop. Trains run hourly between Wye and Charing, facilitating an easy return either to or from your starting point. Featuring an outdoor pool and loads of space, Dormestone House (sleeps 10) serves as an idyllic base, blending historical charm with modern comforts.
Crab & Winkle Way
Stay: Oyster Shore, Whitstable
The Crab & Winkle Way is a delightfully easy 7.5-mile trail linking the coastal town of Whitstable with the historic city of Canterbury. Following the path of one of the world’s oldest passenger railways, the route takes you through Blean Woods, offering a mix of coastal and woodland scenery. Upon reaching Canterbury, explore the city’s rich heritage before hopping on a train back to Whitstable. Oyster Shore (sleeps 8) provides a comfortable seaside haven to relax after your journey.
Romney Marsh Circular
Stay: Romney Marsh Shepherds Huts
Romney Marsh is a landscape like no other – a flat, open expanse with an almost eerie calm. Here, amblers can choose from several circular walks that guide you through grazing lands dotted with medieval churches, each telling a story of the area’s rich history. The flat terrain makes for easy walking, allowing you to fully immerse yourself in the serene environment. After your walk, enjoy a well-earned meal at The Woolpack Inn. Prolong your enjoyment of the countryside with a stay at the Romney Marsh Huts (sleeps 4), which provide a cosy, quiet retreat right on the marshes – perfect for unwinding under the stars.
Belmont Estate Walks
Stay: Crow Cottage & Walnut Tree Cottage, nr Faversham
Set within the leafy grounds of the Belmont Estate, these two properties offer a variety of walks that feel a world away from everyday life. Stroll through manicured gardens, explore ancient woodlands, and enjoy the tranquillity of the estate’s parklands. The well-marked paths cater for all levels of walkers, making it an ideal location for families and even the most casual of hikers. After your walk, indulge in afternoon tea at the Belmont House tearoom, or take a drive to nearby Doddington to savour a meal at The Chequers Inn.
Walk to Whitstable
Stay: Plum Pudding Cottage & The Old Post Office
Located less than three miles from Seasalter (Whitstable’s quieter, western end), these charming cottages are perfect for those looking to explore the coastal beauty of Whitstable. Enjoy leisurely walks along the beach, breathe in the fresh sea air, and perhaps spot some marine life along the way. These routes are gentle and scenic, and lead you to the heart of Whitstable, where you can indulge in fresh seafood at local favourites like JoJo’s or The Lobster Shack. Ideal for lazy days and sundowner walks – you’ll be back for more than just the shellfish.
