Walking through history in winchesters streets
With its cathedral towering over cobbled-stone streets, Winchester is a city filled with history and old English pubs. It might be 2025, but walk the streets of Winchester, and you'll feel as if you're about to meet an important figure from the 15th century.
With a 1.5-hour national express bus directly from London, visiting this city within a day is easy. However, slow travellers like myself will enjoy spending 3 to 5 days here. This is especially true if you plan to visit one of the many nearby market towns using Winchester's public transport.
Due to acquiring free accommodation, I spent quite some time here and am well acquainted with the best places to eat, drink, shop and visit.
There are pubs and cafes on almost every street; however, for food and drink, I recommend…
The Old Gaolhouse JD Wetherspoons
Located in a former prison, Wetherspoons offers affordable pub food and drinks. This old English pub is well-known around the United Kingdom, and is a great spot to settle in for the afternoon and grab a beer.
Winchester City Mill
The cafe inside the Winchester City Mill is perfect for a cup of tea and scones with clotted cream and jam. The mill has been running since the days of King Alfred 1000 years ago, but today, it serves food to lost travellers like myself.
Handlebar Cafe
After hiking Saint Catherine's Hill, visit Handlebar Cafe for lunch. It offers a range of coffees, breakfast options, and toasted sandwiches with garden views.
Hoxton Bakehouse Winchester
Hoxton Bakehouse serves various baked goods, but I recommend buying a croissant here. This bakehouse is also a great spot to take a break from shopping at Winchester's High Street.
After eating too many croissants and scones, you'll need to walk to Saint Catherine's Hill. If you're a hiker who enjoys steep, muddy trails, you can walk to the top of Saint Catherine's Hill via the gate near the cafe. However, the much flatter path around the hill, offering views over the Itchin River, is just as scenic.
Walking along the river from a pub called Bishops on the Bridge is also a nice way to burn calories. This path is also a great starting point for visiting Wolvseey Castle.
Strolling along High Street, the Main Street of Winchester, you'll find a range of boutique and chain stores to browse. Although you'll meet some quirky individuals along this street, I was often impressed by the street performers here. Regardless of whether you're looking to shop till you drop or not, buy a takeaway coffee and watch a busker perform your favourite song.
You can also visit the Winchester markets weeekly on High Street from Thursday to Sunday. These markets are more abundant on weekends, so visit them on Saturday or
For tourist attractions, I recommend visiting...
Winchester City Museum
Wolvseey Castle
Winchester Cathedral and book the guided tour taking you down to the crypt
Winchester Castle
the famous round table at The Great Hall
If you, like me, get lost easily, there is a walking tour called Journey Through Winchester's Past. The tour was unavailable during my stay, but it might be a good option for those only visiting for the day.
A quick note: Since Winchester's streets were built before the invention of cars, parking spaces are limited. As a result, many cars park on pedestrian pathways, so you'll often walk on the road while exploring.
For those looking to stay a little longer, take a train to Portsmouth. With plenty of outlet stores, Portsmouth is perfect for shopping in big brand stores. Adventure seekers will also enjoy the opportunity to abseil from Spinnaker Tower. If you're just looking for a meal with a different view, though, take a seat at Ship Anson.
Other notable towns nearby include Southampton, which has an international airport, and Bournemouth. Although further away, Bath is also a nice town to visit, especially for Bridgetown fans.
Despite the castle ruins and historic buildings, Winchester has certainly found its place in this century as a quick escape from London.
