Exploring Winchester

27 February 2024 by Simon Drayson

Simon Winchester

Winchester is a lovely walkable city, a perfect spot to either put down roots or just enjoy for a day or a weekend. Bursting with character at every turn, it is hard not to find something to catch your eye as you stroll around the high street, or explore the lanes boasting many examples of beautiful period properties.

The city feels connected to nature, with water meadows just to the south and just sitting on the western edge of the stunning South Downs National Park, there is plenty to enjoy from this vibrant city.

With all this charm and, paired with the direct train to London which takes less than an hour, we can understand why it is such a popular city and often features in lists of the best places to live. Here are some of our highlights from our recent visit.

Winchester Guildhall Architecture

Winchester Architecture

Winchester was a capital city from 871, when King Alfred was crowned the King of Wessex and elevated the city. Although it no longer holds this title, it has enjoyed being a city of great importance for many centuries, which is evident in many of the rich and grand architecture dotted across the city. 

Winchester Cathedral is at the heart of the city, the landmark is surrounded by a pretty grass precinct (perfect for summer picnics) with a backdrop of the surrounding rolling Hampshire hills. The original cathedral was founded in 1079 and has been remodeled over the centuries, with rich array of architectural styles still evident. Internally the nave, one of the longest to be found in the UK, is a gothic masterpiece with beautiful pointed arches extending high into the ceiling. 

Winchester College is one of the oldest and most prominent private schools in England, having first been established in 1382, the college is spread over many impressive Listed buildings clustered around College Street near the Cathedral offering an enjoyable walk to get lost amongst the lanes.

Located to the east end of the High Street you can find the rather grand Guildhall, an ornate Victorian building from the 1870’s covered in elaborate stone statues and decorations. Originally built for the police, jails, fire brigade and library, the building is still used for council offices as well as now serving as the largest event space in the city.  

Walking up the High Street you will find a beautiful Butter Cross, or Holy Cross, which dates back to the 15th century. The ornate sculptural cross is positioned on a stepped plinth, making the historic monument a perfect place to sit and enjoy a coffee outside while soaking up the atmosphere. 

If you explore further up the High Steet you can get to the Great Hall, a place not to be missed! The medieval hall has links to English history and legend as within the stunning, gothic aisled hall you can find the iconic Round Table, associated with King Arthur and his knights by the 15th century author Le Morte D’Arthur, who had identified Winchester as Camelot.

The Square Winchester

Eat & Drink in Winchester

You are spoilt for choice in Winchester, with plenty of national restaurants such as The Ivy and Rick Stein. Alongside an array of independents offering a large selection of international cuisine, including delicious independents such as the Gurkhas Inn Nepalese restaurant, the sublime Japanese food at Kyoto Kitchen or Bangkok Bistro for authentic Thai. 

Forte Kitchen is a little gem which is perfect for brunch or lunch, situated just off the main street the welcoming restaurant serves generous sandwiches, delicious cakes and a much needed caffeine hit in the stripped back interior. 

Another pretty spot is The Winchester Orangery, located on The Square just opposite the Cathedral, which offers brunch, coffee and cocktails within the unique interior, complete with its own tree in the middle of the ground floor. 

If you are just looking for a place to enjoy a decent pint, then The Black Boy is our recommendation, located just by the water meadows making it a great stop after a walk. This proper old boozer is made up of a warren of little low ceiled rooms, crammed with an odd collection of memorabilia, collectables and stuffed animals! It really is quite extraordinary.

Winchester High Street George James Architects

Shopping around Winchester

The high street is stocked with many firm favorites, making it a perfect destination for a little retail therapy. It also has many independent gems which are definitely worth searching out. 

If you are a bit of a bookworm then P&G Wells is a must. The shop has been on the site for over 250 years, located on College Street it is a fabulous place to browse for new books, stationery and gifts. Adding to the literary connection of the shop, Jane Austen spent her last few weeks just two doors on College Street, which is why you are sure to find a large collection of her work within. 

We also love stopping in at The Hambledon, a fabulous shop situated on The Square just across from the Cathedral. The shop is spread across three floors of the grand period property, offering a quirky collection of gifts, clothing and accessories which are hard to resist.

Bombay Gin Heatherwick Glasshouse

Nearby in Hampshire

For animal lovers there is Marwell Zoo located just outside Winchester, a 140 acre zoological park where you can get up close to exotic animals such as tigers, snow leopards, giraffes and red pandas. The zoo is set in the grounds of Marwell Hall, now a Grade I listed country house which was largely rebuilt in 1816 by William Long, the original Marwell Hall previously belonged to the Seymour family and is where Henry VIII allegedly married Jane Seymour. 

Just a few miles from Winchester on the is the Laverstoke Distillery, now home to the Bombay Sapphire Gin Distillery and open for tours, which of course conclude with a cocktail! Sitting on the River Test the gin distillery is housed in an old, refurbished red brick mill buildings, sat within the central courtyard is a beautiful contemporary glass installation by Heatherwick Studio. The installation is formed by two intertwined glasshouses, where the botanicals needed for the gin can grow in the temperature controlled environment.  

If you enjoy a National Trust property there are two worth visiting close by, Mottisfont and Hinton Ampner. Mottisfont is a romantic 18th century country house with beautifully landscaped gardens on the River Test. The historic house also has some stunning art to enjoy, with a 20th century art collection on permanent display and an incredible drawing room mural by the British Artist Rex Whistler

Hinton Ampner is an elegant country house with stunning landscaped grounds. The manicured lawns are edged with avenues of topiary and formal boarders, designed to elegantly frame the uninterrupted views across the South Downs. 

The Grange is an impressive example of English Greek Revival Architecture, the original mansion was transformed in the yearly 1800’s into the striking building you can see today, inspired by Greek Temples and classical architecture. Unfortunately, only the shell of the house remains which is free to visit. The house is also used as a magnificent backdrop for The Grange Festival, the annual open air opera, jazz, dance and theatre festival held in the summer.


If you have enjoyed our notes from our exploration around Winchester, you might want to check out our previous articles about other lovely local destinations such as GuildfordFarnhamPetworthChichester and Petersfield

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