A weekend walk through history
Taking the train eliminates the hassle of parking and navigating country roads, allowing you to fully enjoy the scenic beauty of East Sussex. As you travel between Pevensey and Rye, the journey itself becomes part of the experience, with views of rolling hills, rivers, and charming villages along the way. Dogs are also allowed on trains which has been such a bonus for me as I love taking my dog with me on any walk I do!
The best part? With Southern Railway connecting key stops along the way, this journey is easily accessible for a weekend getaway without the need for a car. Below is a guide to how I broke up the walk over two days, incorporating history, nature, and a comfortable overnight stay.
Day 1: Pevensey to Winchelsea
I kicked off my weekend adventure by taking the Southern Railway train to Pevensey, the starting point of the 1066 Country Walk. Pevensey is where William the Conqueror first landed on English soil, and the town’s history is most vividly captured in Pevensey Castle. Originally built by the Romans, it later became a Norman stronghold. Walking through its ancient ruins, it was incredible to imagine the pivotal events that took place here nearly a thousand years ago!
After exploring the castle, I started walking through the idyllic Sussex countryside. The route winds through fields and meadows, offering a peaceful retreat into nature. I made a short detour along the way to Herstmonceux, home to the Herstmonceux Castle and its surrounding gardens. The castle is a beautiful, moated structure from the 15th century, and while it’s a bit off the main route, it was worth the extra miles!
Herstmonceux is also home to the Observatory Science Centre, housed in former Royal Greenwich Observatory buildings. The observatory offers an intriguing blend of history and science, with interactive displays and telescopes to explore. This was something I didn’t know an enormous about, but seeing the size and structures of the telescopes was spectacular. The Science Centre is a fascinating stop, especially for families as there are so many things for children to do and learn about.
From Herstmonceux, continue your journey towards Battle, the believed site of the Battle of Hastings. The 1066 Country Walk takes you to the battlefield itself, where William the Conqueror’s army famously defeated King Harold. Here, you can visit Battle Abbey, founded by William to commemorate his victory. The abbey ruins and visitor centre give a detailed account of the battle and its lasting impact on English history. Standing on what is thought to be the battlefield, it’s hard not to feel the weight of history that surrounds this place.
My last leg of the walk for today led me to Winchelsea, a hilltop village that was once one of England's most important medieval ports. On the way there, I found myself going past the Charles Palmer vineyard which is a great stop for a glass of wine and something to eat to on the journey! Winchelsea’s narrow streets are lined with historic buildings and a lovely sense of calm. I spent some time walking around and loved St. Thomas the Martyr Church, a lovely medieval church with some spectacular stained glass. Beneath the village lies a network of ancient cellars, a relic of its wine-trading past.
Overnight stay: Greyfriars self-catering in Winchelsea
To break up the walk, I spent the night in Greyfriars, a self-catering accommodation located in the heart of Winchelsea (they’re very dog friendly too, although you would never know due to the impeccable interiors!). This peaceful spot offers a chance to rest and recharge in beautiful, modern rooms while still being surrounded by centuries of history. After having walked all day, the stay here was perfect. A true blend of luxury and comfort, with incredible finishes to everything. The treatment from Caroline and Aidan was second to none, they have done the most outstanding job in renovating the accommodation to such a superior standard whilst adhering to strict guidelines due to it being a listed building. With an outdoor hot tub within a private, enclosed, large space for your dog to run around, Greyfriars is perfect for walkers who want to relax. Soak in the hot tub or the bath, walk into town for a meal and to explore, settle into the incredibly inviting sofas and read or watch TV, there’s no shortage of space and activities to help fully escape and decompress. There’s even a private Abbey in the back garden to look out onto. There’s such an overwhelming feeling of peace and tranquillity being here, I left feeling completely pampered and recharged.
Day 2: Winchelsea to Rye
After visiting Battle and the 1066 Story, Battle Abbey and Battlefield, continue your journey toward the historic town of Rye, the final stop on this adventure. The trail from Winchelsea to Rye is a gentle, scenic walk that follows the River Brede and offers some of the most beautiful views of the East Sussex countryside. This section of the walk is shorter, allowing you to take your time and enjoy the natural beauty around you.
Rye is a medieval gem, known for its cobbled streets, half-timbered houses, and centuries of history. Mermaid Street is one of the most famous and photographed streets in England, lined with charming cottages that seem frozen in time. Make sure to visit the Rye Castle Museum to learn about the town’s history of smuggling and defence and take a walk up to the Church of St. Mary to enjoy stunning views of the town and surrounding countryside from its tower.
Southern Railway: Your travel companion
One of the best aspects of this weekend adventure is the convenience offered by Southern Railway. With stations at Pevensey, Winchelsea, and Rye, the railway connects some key points along the 1066 Country Walk, making it easy to travel without a car. Southern Railway provides regular services from London, Brighton, and other major towns, ensuring you can start and finish your walk with ease.
Taking the train eliminates the hassle of parking and navigating country roads, allowing you to fully enjoy the scenic beauty of East Sussex. As you travel between Pevensey and Rye, the journey itself becomes part of the experience, with views of rolling hills, rivers, and charming villages along the way. Dogs are also allowed on trains which has been such a bonus for me as I love taking my dog with me on any walk I do!
Final thoughts
The 1066 Country Walk is a fantastic way to experience the rich history and natural beauty of East Sussex. From the ancient ruins of Pevensey Castle to the historic towns of Battle, Winchelsea, and Rye, every step of the journey offers a glimpse into England’s past. By using Southern Railway to connect the key points of your walk, you can enjoy a stress-free, car-free weekend that combines outdoor adventure with fascinating history.
Whether you’re exploring Norman castles, strolling through medieval towns, or soaking up the beauty of the countryside, the 1066 Walk is a perfect blend of culture, nature, and relaxation. Grab your walking boots, hop on the train, and embark on an unforgettable journey through one of England’s most iconic landscapes.