Winchester – one of the most important cities in England during the Medieval period. Originally founded by the Romans, like so many English cities are, Winchester’s original name was Venta Belgarum. Post Roman withdrawal from England, the city saw constant change before becoming a city of great importance to the Kingdom of Wessex. Winchester is clearly very proud of its legacy, with elements of the city ruins found throughout and an imposing statue of Alfred the Great looking over the main street. However, while the city itself is beautiful and deserves a visit, it is the surrounding countryside that make this place so special. Whether you’re looking for outdoor adventure or a delve into an intriguing past, Winchester genuinely has something for everyone. Below is my suggested list of things to do if you have a day to spend in this historic town.

Discover a Country Market on the Main Street
The first thing to see in any town is always the main street. It gives you a feel for the place you are visiting and is a great way to set up your day. Winchester’s main street is a charming stretch, starting from the old city gate meandering its way to the looming statue of Alfred the Great. The old city gate ruins provide an immediate feel for what this city is about – a glorious town that was once strongly fortified and of clear importance. Ruins are littered throughout the city, not just the main road, and provide a lovely sense of atmosphere and history. If you’re lucky enough, you may be able to line up your visit with the local Farmer’s Market which happens every second Sunday. While not massive, a wide range of producers set-up their stalls on the main street, selling local produce from the region.

See Arthurs ‘Round Table’ at the Great Hall
One of the main attractions of this city is the Great Hall. Situated at the top of the hill by the main entrance gate, the Great Hall is surrounded by ruins of the old fortifications that once protected this city from invaders. The Great Hall is the only part that remains today of a much bigger castle that one stood on the same spot, founded in 1067. The hall itself is large, with towering ceilings to provide a sense of never-ending space. This hall has been used for many high-profile trials over the centuries and the stone seems to carry a certain weight to it, reflecting the many centuries it has seen come and go.
While there are many impressive pieces of art and sculpture in this building, the main attraction is Arthur’s Round Table. Hanging at one end of this imposing space, this replica of King Arthur’s legendary table is a rather incredible sight to see. Made for Henry VIII the table hangs proudly from the ceiling, drawing all eyes towards it. While you’re visiting the Great Hall, don’t forget to pop outside and wander through the small garden. Created for Queen Eleanor, this space is a beautiful replica of a 13th century garden and is a peaceful reprieve from the outside world.
Learn about the History of the Town at the Winchester City Museum
This museum was potentially my least favourite museum in Winchester however it is still worth a visit if you’re visiting with a family. Spread over three floors and housed in an apartment next door to the Cathedral, the Winchester Town Museum takes you on a journey through the history of the city, from prehistoric times to Roman occupation to the Medieval period and beyond. It was a little light on for detail for my liking but very family friendly, filled with lots of interactive exhibits to keep the kids entertained (and potentially make parents exhausted…)
Marvel at Light and Architecture at Winchester Cathedral
Winchester Cathedral is an absolute must add to any day trip itinerary to Winchester. One of the largest Cathedrals in Northern Europe, this imposing building sits just to the side of the main street and is a genuine marvel for all to enjoy. While imposing from the outside, the high ceilings, detailed decorations and stained-glass windows make this Cathedral even more impressive from the inside. First a modest timber building providing a place of worship for the local towns people, the Cathedral saw its first major expansion post the invasion of England under William the Conqueror and then subsequently through the gothic era and the later 17th and 19th centuries. As such, the Cathedral is a beautiful combination of centuries of different architectural styles and predispositions.

Make sure you give yourself plenty of time to explore this monument before the closing time. The Cathedral is filled with alcoves to explore, each providing a new piece of beauty to experience. There are also often additional exhibitions held within the Cathedral which are worth enjoying. During my visit the Kings & Scribes exhibition was open which provided a fascinating look into the history of this impressive building and the historical figures who contributed to its creation and everyday upkeep.
Immerse Yourself in the Past at Wolvesey Castle
If you’re someone who loves a good Roman ruin, this one is for you. Situated near the main university buildings, Wolvesey Castle are the ruins of the old Bishop of Winchester’s residence. These sprawling ruins are much bigger than I would have expected and provide an idea of how important and prosperous Winchester once was, and still is. The ruins are clearly signposted, with plaques placed throughout to provide you context on what you are looking at and what the rooms may once have been used for. Wander through the stones and imagine what life might have been like at the height of this imposing building before it was left for nature to reclaim. Best part is it’s completely free to visit!

Put on your Walking Boots and Explore
While the town centre and Cathedral themselves are beautiful, Winchester really comes to life when you explore the walking tracks around the city. The surrounding countryside is incredibly beautiful and all very accessible. Winchester is circled by a long river called the Itchen River, one of the many reasons this spot was originally chosen for settlement. There are many paths along this river which take you beyond the city centre and provide a very different view of Winchester. Walk along the river’s edge and enter a fairytale world. If you’re feeling adventurous enough, walk yourself to St Catherine’s Hill and take some time to enjoy the view from the top. Then take the river path back to the city centre and enjoy the quaint country air, the flowing water and the old-world houses that line the river path and ooze charisma. I visited in Autumn and the golden and orange tones made this path seem all that more magical. One caution, the paths can get extremely wet and muddy if you find yourself visiting with the rain so be prepared to come out of this walk a little dirty.

Enjoy the Culinary Delights on Offer
One thing many may not know about Winchester is its abundance of culinary delights. The city is filled with cute cafes and delicious restaurants it’s almost too hard to pick where to stop. Below are some of the favourite places I stopped at to help you choose.
- Incognito – Bar
We are going to start with my pick of the bunch – Incognito. This bar is an absolute must visit and I cannot stress this enough! A proper hidden bar – the entrance is a nondescript door on a side street that I only saw because someone happened to exit from it as I was walking by – this bar oozes class and mystery. The interior is dark but inviting, the décor is quirky, and the bar is centred on a story of travel and intrigue (I’m not going to ruin it for you here!) which immediately creates an atmosphere of adventure and fun. From a cocktail perspective, this bar is all about funky and innovative cocktail ideas. Think a morning breakfast cocktail where you pour your cocktail from a teapot into your glass and eat a faux egg made of custard. Or a cocktail where you have to play a game to access your drink. This bar is all about the theatrics without being tacky. - Winchester Bakery – Bakery and Café
This was a cute little, double storey bakery on the main street. Selling all kinds of different baked goods, the bread itself was extremely delicious. An added benefit to buying some bread at this shop is that you get a free coffee with any bread purchase. Buy your bread, order you coffee and head upstairs to enjoy a little rest before you properly start exploring. - The Black Boy – Pub
This pub sits close to the river’s edge and is everything you could imagine of a classic English pub. The ceilings are low, the interior is warm and comforting and there is a very pretty outdoor area if the weather is nice. This is the perfect place if you’re looking for a cosy drink in the afternoon and want to experience the classic, British pub life. - Winchester Stable – Pizza Restaurant
Despite being a chain, the pizzas here were yum and the energy was lively. This restaurant sits on one of the main streets nearby the Cathedral and there are so many options to choose from you almost can’t go wrong. However, if you’re struggling to decide, The Winchester Stable is a solid choice. One flag is that the restaurant is usually very busy of a weekend and the inside can be completely booked. They do have some seating out the front of the restaurant however be careful if it’s a rainy day – I was unfortunate enough to get caught in the rain while eating my pizza!
If you are looking for a place to visit that is slightly away from the major England attractions, I would highly recommend Winchester. The city is charming, the food and drink options are ample, and the surrounding countryside is breathtaking. It’s a place where you can spend a third of your day enjoying local attractions, a third of your day eating and drinking and a third of your day walking the countryside!


Leave a comment