If you want to dip your toe into somewhere special, 48 hours in East Sussex is a good place to start. With many places in the county only a little over an hour from London, and less from Gatwick, Sussex is a place where you’ll find thousands of years of history, the dramatic chalk paths of the South Downs, the soft curves of the Weald, medieval villages and towns, and a positive glut of award-winning vineyards, producers and eateries.
This second in our “48-hours in Sussex” self-guided itineraries series introduces you to the heart and soul of Sussex. It weaves together the places, landscapes, history and people that have shaped the county over centuries, offering an authentic taste of what makes Sussex unlike anywhere else in England.
48 hours in East Sussex
- Day One: Arrive in Lewes by train from London. Explore the town before travelling to Alfriston by train, bus or taxi (typically via Polegate). Spend the afternoon and evening in Alfriston.
- Day Two: Travel to Hastings Old Town (usually changing trains at Polegate) and spend the day exploring the seafront and historic attractions before returning to London by rail.
Lewes
Set in a gap in the South Downs and on the banks of the River Ouse, Lewes is one of England’s most characterful market towns. First recorded in 961 and appearing in the Domesday Book of 1086, its rich history oozes from almost every brick and corner. The imposing Norman castle dominates the top of the town, while the nearby ruins of Lewes Priory hint at the town’s medieval importance. Over the centuries, Lewes has been shaped by momentous events, from the Battle of Lewes in 1264 to its famous Bonfire celebrations, and it has also been home to remarkable figures including Thomas Paine.
Today, Lewes effortlessly blends its historic past with a vibrant, creative present. Wander down the High Street from the castle, taking in magnificent views of the South Downs as you pass handsome period buildings, independent bookshops, artisan workshops, cafés, galleries and specialist shops. Stroll beside the River Ouse, explore the peaceful gardens at Southover Grange, discover exhibitions at Charleston in Lewes or catch a film at The Depot, a converted warehouse by the station. With footpaths leading straight onto the South Downs, an energetic arts scene and a fiercely independent spirit, Lewes is a town where history and modern life sit comfortably together.
Top three things to see in Lewes:
- Lewes Castle – For its fascinating history and panoramic views across the town and the South Downs.
- Southover Grange Gardens – Beautiful historic gardens that are often overlooked and make a peaceful stop.
- Lewes Flea Market – A treasure trove of antiques, vintage finds and curiosities that perfectly captures the town’s quirky, independent character.
Alfriston
Often described as one of England’s prettiest villages, Alfriston sits in the picturesque Cuckmere Valley, surrounded by the rolling South Downs. Mentioned in the Domesday Book, its narrow High Street is lined with centuries of history, from medieval timber-framed cottages to ancient inns that have welcomed travellers for hundreds of years. The Star Inn, built in 1345 as a hostel for monks and pilgrims travelling between Battle Abbey and Chichester Cathedral, later became an inn and still displays its famous Red Lion figurehead, said to have been taken from the prow of a smuggling ship. Nearby stand other historic buildings, including the elegant The Alfriston, formerly Deans Place Hotel, and the charming Market Square with its traditional Sussex inns.
At the heart of the village lies the Tye, one of the largest village greens in England, overlooked by St Andrew’s Church, affectionately known as the “Cathedral of the South Downs”. Beside it stands the 14th-century Alfriston Clergy House, the first property ever acquired by the National Trust in 1896 and a classic example of a Wealden house. Today, Alfriston combines its remarkable heritage with independent shops, welcoming cafés and easy access to the South Downs Way, making it the perfect place to slow down and enjoy the Sussex countryside.
Three things to do in Alfriston:
- Rathfinny Wine Estate – Tour the vineyard, enjoy a tasting, dine overlooking the South Downs or stay overnight.
- St Andrew’s Church – The celebrated “Cathedral of the South Downs” is one of Sussex’s finest medieval churches.
- Walk part of the South Downs Way – Even a short stroll from the village rewards you with pretty views of the Cuckmere Valley.
Hastings Old Town
From Alfriston, continue by road or train to Hastings before making your way to the atmospheric Old Town, one of the most distinctive and characterful places in Sussex. Towered over by East and West Hills, with the broad shingle beach of the Stade stretching out before it, Hastings Old Town is where the county’s fishing heritage is still very much alive. Home to Europe’s largest beach-launched fishing fleet, colourful boats are hauled directly onto the shore beneath the town’s iconic black net shops, tall timber buildings that have become one of Sussex’s most recognisable landmarks.
Behind the beach, a maze of narrow streets and ancient twittens reveals a wonderfully bohemian quarter filled with independent cafés, antique shops, galleries, bookshops and boutiques. Wander along George Street and the High Street before climbing the West Hill to the ruins of Hastings Castle, the first castle built by William the Conqueror after the Norman Conquest, or explore the mysterious Smugglers’ Adventure in the caves within the hill. For sweeping views across the Old Town and coastline, ride the historic cliff railway to the top of East Cliff. Rich in history yet effortlessly creative, Hastings Old Town is a place where tradition, art and the sea combine to create an unforgettable finale to your East Sussex adventure.
Top Three Things to Do in Hastings Old Town:
- Visit Hastings Castle – The dramatic ruins of William the Conqueror’s first English castle.
- Dine at Webbe’s Rock-a-Nore – Just metres from the fishing boats and iconic net shops, Webbe’s celebrates the very best of the Hastings fishing fleet, with seafood travelling from boat to plate in minutes.
- Explore Hastings Country Park – Leave the bustle of the Old Town behind and climb onto the East Hill, where clifftop paths wind through one of Britain’s most beautiful coastal landscapes.
As your 48 hours draw to a close, hop on the train home or jump back in the car. You’ll leave with memories of medieval streets, rolling downland, ancient churches, fishing boats and dramatic coastline but also the feeling that you’ve only scratched the surface. Sussex has a habit of drawing people back, so why not start planning your next 48-hour adventure… this time in West Sussex?
