Guide to Winchester: Best Things to Do in Winchester, UK

Last Updated on 20th September 2022 by Sophie Nadeau

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Winchester and its surrounding area have been inhabited since time immemorial. And you can tell. Here’s a quick guide to Winchester and the very best things to do in Winchester!

During Roman times, the town was known as ‘Venta Belgarum’ (the Belgae were a local tribe while ‘venta’ means town/ meeting place in Celtic). It was also one of the first cities in the UK to be built in a ‘grid’ pattern and is not far from the historic settlement of Old Sarum.

Best known for its farmer’s markets, ancient cathedral, and rich history, the population of Winchester hovers around 45,000, making it one of the UK’s smallest cities. While the weather is often cloudy, rainy, and windy (it is in England, after all), the city is well worth a visit, if only to discover the Roundtable of Arthurian Legend!

Best things to do in Winchester

Walk down the Oldest High Street in Britain

If you’re looking for what to do in Winchester, then the first item on your agenda should simply be to stroll down the ancient city’s historic high street. The road has been littered with stores ever since Roman times, making it the oldest high street in Britain.

There is an interesting mix of corporate brands intermingled with independent boutiques, creating a unique vibe where local and global businesses are able to coexist.

Many of Winchester’s storefronts have façades demonstrating rare examples of Elizabethan and Regency architecture, allowing for one of the more memorable UK High Street shopping experiences. For an even greater insight into Winchester’s history, consider booking a walking tour like this one.

Visit Westgate Museum

Originally a debtors prison for over 150 years, this now turned museum offers a fascinating insight into Winchester throughout the ages. As well as housing numerous archaeological finds and historical documentation from throughout the city, this grade one listed building has numerous original steep staircases and even offers incredible rooftop views over the city of Winchester.

Although many of the activities inside the museum are primarily aimed at children, it was still fun to try on armour and create brass rubbings! Another must-see activity of the Westgate Museum was ascending the narrow and steep staircase to get onto the building’s roof. Wander up the small space and you’ll be rewarded with beautiful views over the ancient city.

Wander through Winchester Cathedral

While the current building was erected during the 11th century, Winchester has had a cathedral since 642 AD. It is not only one of the largest Cathedrals in England, but also has the longest nave of any Gothic Cathedral in Europe, if not the World.

One of the more peculiar features of the cathedral is the abstract design of the West Window. At the outbreak of the English civil war in 1642, Cromwell’s forces purposely smashed the great stained glass windows.

With the restoration of the Monarch just under twenty years later, the pieces were randomly gathered up and used to create an abstract pattern. The interior of Winchester Cathedral was also used for filming in Dan Brown’s, the Da Vinci Code and also Netflix’s hit show The Crown.

Search for King Arthur in The Great Hall & See the Round Table

Legend has it that the original roundtable from Arthurian legend hangs in the great hall of Winchester. Although subsequent research has shown that the table was most probably created many centuries after Arthur is supposed to have lived (it was probably made in the 13th Century), it is still an amazing piece of history.

And upon the table itself, if you look closely and through the layers of dust that have since accumulated, you’ll find written the inscription ‘rownde table of kyng Arthur with 24 of his namyde knyattes’Elsewhere in the UK, the supposed birthplace of King Arthur is said to be Tintagel in North Cornwall.

The hall itself is all that survives of the previous Winchester castle; the rest of the building having been demolished upon Cromwell’s order in the late 1640s. Notably, Sir Walter Raleigh, who was arrested in a small pub in Ashburton on the fringes of Dartmoor National Park, was a Buccaneer (fancy name for a pirate) who stood trial in Winchester in 1603 for plotting against the King!

Wander out of the hall and there’s a garden nearby which is a recreation of what a medieval herbarium would have looked like. Aptly named ‘Queen Eleanor’s Garden,’ it’s filled with chamomile, bay, various herbs, and even a fountain. If you’re looking for a quiet place in Winchester to enjoy a sandwich, read a book, or sit and watch the world go by for a little while.

Soak up Some History in Cathedral Close

A sea of tranquillity in one of the most compact cities in the UK, one of the very best things to do in Winchester is to head to the Cathedral Close. The area and its surrounds have been a meeting point for people of all ages for centuries, and traces of history can be seen in the well-worn steps of the square, as well as the worn façade of the cathedral itself.

Pictured below a hidden gem of Winchester: Curle’s Passage, a 1632 passageway created in order to allow visitors to wander in and out of Inner and Outer Cathedral Closes without the need to go through the Cathedral itself.

Explore the Green Spaces Winchester Has to Offer

Having been built using a grid system, green spaces were an integral in planning the city’s structure. Green spaces can be found abundantly throughout the many narrow cobbled streets and make for one of the best Winchester attractions.

These parks, gardens, and green spaces are the perfect place for a summer picnic or a breath of fresh air and drinking some hot chocolate on a cool river walk during the winter months.

Take a day trip to Salisbury

Salisbury is an equally beautiful destination just an hour away from Winchester via train. Salisbury can easily be visited as a day trip from Winchester and highlights of the city include a cathedral which has the highest spire in England, and a Queen Anne Townhouse (Mompesson House) which was used as a filming location for the 1995 Sense and Sensibility movie.

Other places of note in Salisbury include the recently renovated Salisbury Museum and its ease of access to the nearby historical sites of Stonehenge and Avebury, as well as the forgotten village of Imber (accessible only at certain times of the year).

For those wishing to combine several historic cities as an excursion from London, a visit to Salisbury can easily be combined with a trip to Winchester over the course of a weekend.

Walk along the River Itchen

The pretty River Itchen flows through the city, providing water for all. In fact, it was probably the very reason that people decided to settle in Winchester city over two millennia ago.

Of all the things to do in Winchester, this may seem the least obvious, but it may also well end up being the most rewarding. After all, today, the river banks give life to an oasis of greenery and are even home to the increasingly rare otter!

When to visit Winchester

With transport links in the form of trains and buses, it’s possible to visit Winchester all year ’round. For those wishing to catch flights to the UK, it’s worth noting that Winchester is connected directly to London via both train and bus.

With this being said, when you personally visit Winchester depends entirely on your personal preference. If you’re looking for a more laid back pace while everything is open, then visiting in the European shoulder seasons (i.e. spring or autumn) is probably the best option for you.

A visit in the summer will guarantee the best weather, while a trip during the winter will mean that you pretty much get the city to yourself. All in all, the choice of when to visit Winchester is totally up to you and your travel plans!

Where to stay in Winchester

Although you could easily see most of Winchester’s main attractions in just one day, the city is best explored over the course of a long weekend, allowing for time to take day trips and soaking up all of the history this quirky destination has to offer. Here are some recommendations for where to stay in Winchester:

Lainston House

A former mansion set amidst a beautiful estate, this 17th-century country house is now a five-star luxury hotel that’s part of the Exclusive Hotel chain. Check prices and availability here.

The Winchester Royal Hotel

Beautiful and luxurious, this 4-star hotel is situated right in the heart of the city, not far from many of Winchester’s main attractions. Check prices and availability here.

Hannah’s

Over the years, what is now Hannah’s Bed and Breakfast has served many functions. The building on Parchment Street was once used as a stables, a dance hall and warehouse has since been transformed into a boutique accommodation you’ll love staying during any trip to the city. Check prices and availability here.

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