Fun & Quirky Things To Do In Winchester, England

Last Updated on 14th September 2023

This post about quirky things to do in Winchester contains affiliate links and some experiences featured was part of a collaborative press trip, please see my disclaimer for more.

Situated in the county of Hampshire, on the edge of the South Downs National Park, Winchester is a relatively small city that packs a punch when it comes to history, food, culture and architecture.

We spent two nights in Winchester in February 2023 as part of a collaborative press trip and even though it wasn’t really a place that was on my UK bucket list before our adventure, it’s now a place that I would happily recommend anyone to visit while in the south of England.

Below, you can find my ultimate guide to the best fun and quirky things to do in Winchester, England, including where to stay, what to do and where to eat!

Is Winchester UK worth visiting?

Winchester is 100% worth visiting! It’s such a small, but gorgeous university city with a great food scene, an abundance of history and beautiful sights to explore!

The historic city of Winchester was once the capital of England and it’s positively teeming with fascinating stories, remarkable feats of architecture and historic tales.

Where to stay in Winchester

As part of our collaborative press trip to Winchester, we were very kindly treated to a two-night stay at The Wykeham Arms; a fantastic pub nestled in the heart of the city with excellent rooms that are perfect for a weekend in Winchester.

From the outside, The Wykeham Arms appears to be quite unassuming, but as soon as you step foot inside this cosy establishment, you’re greeted by friendly staff, a warm pub, delectable food and gorgeous rooms.

I was a bit apprehensive about staying above a pub at first as I assumed that it would be incredibly noisy all night long with drinkers downstairs, but it was actually extraordinarily quiet! When we arrived back each evening, the pub was teeming with people, but as soon as we retreated to the confines of our room upstairs, we couldn’t hear a thing!

The rooms at The Wykeham Arms in Winchester offer an old-worldly charm with modern conveniences. The walls are decorated with framed historic photographs and dazzling chandeliers, but the mod-cons of a state-of-the-art coffee machine, a complimentary mini-bar, a giant comfy bed and a wall-mounted TV make your stay incredibly comfortable and convenient.

As part of our stay at The Wykeham Arms, we were also treated to a complimentary breakfast each morning. The breakfast menu is vast and extensive, with popular favourites such as granola, muesli, porridge, full English breakfast, eggs benedict, and eggs royale, as well as plenty of vegetarian and vegan options as well.

I opted for the full English breakfast each morning as it was absolutely wonderful, but the rest of the food also looked incredible!

If you’re looking for somewhere to stay in Winchester, I really couldn’t recommend The Wykeham Arms enough!

Book a stay at The Wykeham Arms here!

Fun & quirky things to do in Winchester, England

If you’re looking for the best quirky and unusual things to do in Winchester, check out my thorough guide below!

1. Winchester Cathedral – quirky things to do in Winchester city centre

With a history spanning more than 1000 years, Winchester Cathedral is arguably the most important and prominent tourist attraction in the city.

As part of our visit to Winchester, we were lucky enough to take a tour of the cathedral’s tower, which included a walk along the full length of the nave roof, as well as a visit to the bell-ringing room and the outdoor rooftop as well.

I’d highly recommend booking a tower tour of Winchester Cathedral, especially if you’re a history and architecture fanatic as the views of both the inside and outside of the cathedral are stunning. Be warned though; it’s not for the faint-hearted!

There are 213 incredibly steep and narrow steps to climb and the winding staircase is also crazy narrow, so it’s not ideal for those who suffer from claustrophobia. However, if you can brave the climb, it’s worth it!

The tower tour lasted just less than two hours, which was probably a tad too long for my liking, but it did mean that we saw as much of the beautiful cathedral as possible and learnt all about its enigmatic history.

I won’t give too much detail away about what you can expect, as I think it’s well worth learning about for yourself!

2. The Great Hall

The Great Hall contains one of the most fascinating pieces of medieval mythology; King Arthur’s Round Table.

I’d heard plenty of legends about King Arthur and his infamous Round Table, but nothing prepared me for just how big it is in real life! The table is also the only remaining artefact of Winchester Castle and as it sits proudly against a giant wall, it’s truly remarkable to see just how enormous it is!

We visited Winchester in early February and we were the only people inside the Great Hall, even when visiting in the afternoon! It was almost eerily quiet inside the expansive halls, but we had a truly awesome time learning about the legends of King Arthur, as well as some of the historic facts about the world-renowned Round Table.

3. 878AD – the best Winchester attractions

878AD is one of Winchester’s newest attractions, having only opened in late 2022, but it’s already on its way to making its mark on the tourist scene in the city.

It offers an immersive experience with live performers recreating the lives of the people who would have lived in Anglo-Saxon Winchester, as well as boasting an augmented reality experience once you’ve concluded your visit where you can explore the city of Winchester via the interactive app.

You’ll learn all about the history of the Anglo-Saxons, primarily the events of the Battle of Edington, on an interactive exploration throughout the museum and beyond.

It’s a great attraction to visit with kids in Winchester as well, as it offers both an educational experience, while still being fun!

4. City Museum

The City Museum takes you on a journey through the ancient capital’s vibrant past, including its origins as an Iron Age trading centre, what it was like in the Anglo-Saxon days, as well as how the famous writer Jane Austen spent her final days in the city.

You can also find the “Winchester Model” which is a scale model of the historic city during Victorian times.

5. Winchester College

Situated right in the heart of the city, Winchester College has the longest continuous history of any English school, which is a mighty impressive claim considering just how many prestigious, historic schools there are in England!

It’s famous for being the education facility for many politicians, writers, scientists and other acclaimed academia over its lifetime.

You can tour various parts of the college, including the Treasury, which houses various artefacts, artworks and archaeological discoveries from Egypt, Rome , Greece and more.

6. Jane Austen House

Renowned for being one of the world’s greatest novelists, who wrote famous literature such as Pride and Prejudice, Jane Austen spent her final years living on College Street in Winchester.

Unfortunately, you can’t go inside the house today as it’s now a private residence, but you can stroll past it on your way to Winchester Cathedral and see it from the outside.

7. Keats’ Walk – fun and quirky things to do in Winchester this weekend

If you’ve had enough historic exploration, head to the nearby riverwalk known as Keats’ walk which is named as such after the famous poet who used to frequent this path during his stay in Winchester.

I’ve embedded a map below so you can find the exact route that will take you from the Cathedral and past the grounds of Winchester College, concluding at Garnier Road where you can loop back into the city centre.

8. Kingsgate and Priors Gate

If you’ve visited my beloved hometown of York, you’ll likely be aware of the Roman city walls (known as the Bar Walls in York) and Winchester has its own version of Roman fortifications, known as Kingsgate and Priors Gate.

These two gates are the only surviving medieval gates of their kind in the city of Winchester and considering they’re hundreds of years old, they’ve certainly stood the test of time!

Inside the passageway of Kingsgate, you’ll find Kingsgate Books & Prints which is an awesome place to pick up souvenirs or to purchase a book for a fraction of its retail price.

9. The Castle passageways – quirky things to do in Winchester

Adjacent to the Great Hall, you’ll find the passageway remains of Winchester Castle which once stood on the site over 800 years ago.

Today, all that remains of the castle is the Great Hall (and the Round Table) and the ancient ruins of the passageways which you can explore free of charge.

10. Guildhall Winchester

This lavish feat of architecture is a multifunctional events space that hosts hundreds of important meetings and events throughout the year.

From the outside, its grand facade is mightily impressive to admire, so even if you don’t have any events planned inside the Guildhall, it’s still worth a stroll past to admire from the outside.

11. Old Fashioned Sweetie Shop – fun and quirky things to do in Winchester

We stumbled across the Old Fashioned Sweetie Shop on our way to the Great Hall, but it was a delightful discovery as we found so many of our favourite sweets inside!

I even found a pack of my mum’s favourite sweets from the 80s which she was absolutely thrilled by! Be sure to have a nosey inside if you’ve got a penchant for something sweet and delicious!

12. Cornflowers Gift Shop

Situated just around the corner from The Wykeham Arms, Cornflowers Gift Shop was a brilliant discovery during our two days in Winchester as it stocks an assortment of wonderful souvenirs such as notebooks, ornaments, teddies, mugs, scarves, candles and so much more!

13. P&G Wells bookshop

You’ll find P&G Wells Bookstore just a couple of doors down from the Jane Austen house and this wonderful antique store is sure to delight book lovers from all over the world!

Not only is its facade absolutely beautiful, but the inside of P&G Wells is also full of both classic literary treasures and new releases.

The best places to eat in Winchester

During our weekend in Winchester, we ate like royalty, which felt very apt considering we were in one of the oldest and most prestigious cities in England!

If you’re looking for the best places to eat in Winchester, including the best cafes, bars, pubs and restaurants, I’ve got you covered with my top recommendations below!

1. The Chesil Rectory – top restaurants in Winchester

Located inside the oldest building in Winchester, the Chesil Rectory is not only my number one recommendation of the best places to eat in Winchester, but it’s probably one of the best places I’ve eaten in the whole of England!

This wonderful restaurant is an absolute dream place to eat; its interior is just as grand and romantic as its elegant facade and the food is genuinely some of the best I’ve had in a very long time!

The menu is relatively short and simple, with highlights such as ham hock terrine, pan-fried hake and venison, but each and every dish is a delight for the senses.

I had the confit pork belly with vanilla and apple purée, cabbage, cider jus and crackling. This meal was truly delightful; the pork belly was the best I’ve ever had, the cabbage combined with the cider jus tasted absolutely phenomenal and the whole dish just worked perfectly.

Matt opted for the Loch Duart salmon which was served with potato fondant, crab bon bon, coastal sea vegetables and saffron aioli. I don’t like salmon at all so I didn’t even try this dish, but Matt couldn’t rave about it enough and he said it was some of the best salmon he’d ever had!

For dessert, we shared the chocolate moose with coffee ice cream and despite not being the biggest fan of coffee, I couldn’t believe how well it paired with the chocolate moose.

The staff at the Chesil Rectory were also outstanding and I really can’t rate this amazing restaurant enough; if there’s just one place I would recommend to eat in Winchester, it has to be here!

2. The Wykeham Arms

I’ve already mentioned the wonderful breakfast we enjoyed at The Wykeham Arms as part of our stay in Winchester in the section above, but I also wanted to highlight it here as well as not only do they offer up some incredible breakfast dishes, but they also have a wonderful pub grub lunch and evening menu!

If you’re looking for some truly special classic pub food such as pies, burgers, steak and fish and chips, you’re in for a real treat at The Wykeham Arms!

3. South Downs Social

After visiting 878AD, we headed just over the road to South Downs Social where we were invited to try some of the awesome dishes on their lunch menu.

Neil, the owner behind South Downs Social, is the most friendly guy and he happily chatted with us for a while until our food arrived. Not only is South Downs Social a fantastic cafe/coffee shop, but it’s also a cycling-centred establishment that welcomes cyclists from all over the country and beyond!

The menu at South Downs Social is vast and extensive and we had a hard time choosing just one thing to eat! In the end, we settled for the signature hot chocolate and the pastrami sandwich, which were excellent choices!

4. Overdraft Beer and Tacos

We didn’t have anywhere booked for dinner on our first night in Winchester and we originally wanted to check out Piecaramba as it’s one of the most highly rated places to eat in the city, but as that was closed due to a staff party, we headed to a nearby bar called Overdraft Beer and Tacos instead.

While it wasn’t our first choice, Overdraft Beer and Tacos certainly was a very good choice! I had the pulled chicken in adobo tacos and Matt had the braised beef brisket tacos and we also shared a portion of loaded nachos.

The nachos weren’t the best I’ve ever had but the tacos were pretty good!

5. The Royal Oak – places to eat in Winchester town centre

We came across The Royal Oak on our way back to The Wykeham Arms one evening and after seeing the sign outside where it claimed to be the “oldest pub in England” (although we later discovered that this wasn’t technically true as it’s just the underground cellar part that’s the oldest in England!), we ventured inside for a drink.

It’s a lovely, cosy establishment with plenty of beer and cider on tap and a vast variety of wines to choose from. They also have a great pub food menu, but we didn’t get the chance to sample anything as we’d just eaten!

Some other great places to eat in Winchester include Piecaramba (we tried to eat here on our first night but it was closed for a staff party!), Three Joes Sourdough Pizza and The Stable.

Best quirky things to do near Winchester

While there are plenty of awesome and fun attractions in Winchester to enjoy, if you plan to spend a little longer in the area, I’ve also included a few ideas of the best things to do around Winchester (within an hour’s drive) for even more fun!

• Spend a day in the nearby city of Southhampton (a 25-minute drive)
• Visit Stonehenge (a 45-minute drive)
• Check out Marwell Zoo (a 20-minute drive)
• Experience the Winchester Science Centre & Planetarium (a 10-minute drive)
• Go hiking in the South Downs National Park

Our time in Winchester was truly lovely and even though it’s only a small city, I wouldn’t hesitate to head back in the future for a little UK city break as it’s such a beautiful and welcoming place with plenty of things to see, do and eat! There are so many fun and quirky things to do in Winchester that you should definitely have it on your UK bucket list!

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Have you ever visited Winchester in England? Is it somewhere you’d like to visit for a weekend break in the UK? Let me know in the comments or on Instagram at @imjustagirl_16.