How to spend a day in beautiful Winchester

A guide to visiting Winchester

At the end of last year, I desperately wanted to get out of London for a couple of days to enjoy the countryside.

After throwing around ideas, I finally decided upon Winchester. To tell you the truth, I knew little about the place, other than it being a small medieval city that’s home to one of the biggest Cathedrals in the country.

With little to go on, I didn’t really have any expectations other than enjoying the discovery of somewhere new. But Winchester ended up surpassing any expectations I had. Not only did it charm me with its eclectic architecture, I was also rewarded by its significant place in history and literature (embarrassingly, I didn’t even know it was the first and former capital of England!).

So whether you’re already living in England, or only visiting and want to experience a city that has olde-wordle charm, look no further than Winchester. It has all the enchanting qualities of quintessential England to make you feel like you’ve trodden back in time. Furthermore, with its close proximity to London, it’s incredibly easy to reach by train or car.

Winchester, England, travel guide

1. Visit Winchester Cathedral

Upon arrival in Winchester we figured we’d start with its most famous landmark: the cathedral. The external walls of the building are impressive, but what lies waiting inside is even more impressive. I looked up at the ceiling and almost had to pick my jaw back up off the floor.

Not only is the cathedral one of the biggest England has to offer, it’s also one of the world’s longest medieval churches.

Another fascinating fact is that Jane Austen is buried here along with other important figures. In case you’re not familiar with English writers, Jane Austen was an 18th Century writer whose legacy includes such works as Pride and Prejudice, Sense and Sensibility and Emma.

If you love Period dramas, there’s a strong chance you’ve seen at least one of the film adaptations. With fifteen centuries of history behind it, kings buried within its walls, and endless legends circulating around it, the cathedral is an inseparable part of Winchester’s heritage.

One of the most unique aspects of the cathedral are the crypts. Sadly, due to Covid they weren’t open when I visited, but among the stone archways you’ll find a sculpture by Anthony Gormley – one of the UK’s most famous contemporary artists. By missing it this time, I have more reasons to return.

On top of visiting Jane Austen’s tombstone inside the cathedral, you can also see the place where she lived which has a blue plaque on the wall.

2. Explore the ruins of Wolvesey Castle

Only a short walk away from Winchester Cathedral is Wolvesey Castle, once home to the Bishops of Winchester throughout the Middle Ages, with the extensive remains dating from the 12th century.

You can walk among the ruins and imagine how it would have been in its glory years when it hosted Queen Mary I and Philip of Spain in 1554. But those days weren’t to last when it fell victim to destruction in 1646 during the English Civil War.

3. Walk up to St Giles Hill Viewpoint

After, it was time to see the city from its highest point at St Giles Hill. We passed the ruins of the city wall, the iconic stone bridge and wind mill and soaked up the bucolic atmosphere for a few moments. Then we followed the sign posts up Magdalen Hill and on towards St Giles Hill which opens up to a wide green space at the top and the viewpoint is located on the left lower side.

4. Admire the buildings and potter around the shops

Perhaps my favourite activity in Winchester was simply roaming around the streets, where’s there’s plenty of opportunity to admire Harry Potter-esque architecture complete with narrow lanes and cobbled streets.

As you would expect from a well-preserved medieval town centre, you can discover a large collection of half-timber facades. Many of these reminded me of Canterbury in Kent which is another place to put on your list if you haven’t already been.

If you’re still after some of the main attractions, make you’re way to The Great Hall – famed as the finest surviving aisled hall of the 13th century, and hear about King Arthur’s Round Table.

Where to eat in Winchester

There are lots of restaurants and cosy cafes for you to choose to from in Winchester. I had my eyes set on the menu at Bugle Inn, which prides itself on sourcing local produce, but without a reservation, the restaurant was fully booked. Ahem.

We looked at other options and great reviews kept popping up for Piecaramba – as the name suggests it’s a joint specialising in pies – hardly the hit of luxury we first thought about, but good food is good food, right?

Admittedly, it’s not often that you’ll find me scoffing down pies, but on a cold and crisp day in early December the idea of something hearty was tempting.

As I stepped into the place and clapped eyes on the titanic-sized pies – the biggest I’d seen – complete with mash potatoes submerged in thick gravy, I understood what all the fuss was about. Adding to my delight was the quirky interior, the walls were plastered with comics and at our table was a Super Nintendo which passed the time while we were waiting.

When the menu came, I realised the biggest was called the Piefull Tower which was essentially two pies piled on top of each other. While it looked incredibly scrumptious, I opted for the veggie pie which was rather more humble in size, but unforgettably delicious and more than enough!

Where to stay in Winchester

There’s a nice array of hotels and B&Bs available in Winchester. I stayed at The Old Vine which is hard to beat in terms of location. It’s located just steps from the Cathedral and all the main attractions I listed in the guide are within 20-minutes walk.

The building itself is very charming with period features and character. It is located on the grounds of a local gastropub, so needlessly to say, you won’t have to worry about food. They’ve got you covered! 

Are you planning a trip to Winchester?

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Hi, I'm Shing

Welcome to The Culture Map, a place where I share my travel guides, adventurous tales, and capture the inspiring diversity of our world.

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