A Complete Guide To The Perfect Weekend Break In Chester

I recently made a last-minute decision to take a weekend break in Chester while travelling from Manchester to London. And no – before you check Google maps, it’s definitely not on the way. Chester isn’t the place you’d stop to ‘break up a journey’. In fact, it takes just as long to get to London from Chester as it does from Manchester.

Geographically pointless? Maybe. But I’m a big fan of spontaneous detours, especially when they lead me somewhere completely new.

Chester is a picturesque city in Cheshire on the River Dee. Tucked between Manchester and Liverpool, Chester could easily fly under the radar of its bigger, louder neighbours. But honestly? This city has a charm of its own; steeped in history, packed with character and way more stylish than you’d expect for a city of its size. I was genuinely surprised by just how much punch Chester packs into such a compact space. 

So if you’re thinking about a UK weekend break, here’s my guide on how to spend a weekend in Chester – what to see, where to eat, stay and all the good stuff in between. 

If you’ve only got one day in Chester, don’t worry – this charming little city knows how to make a lasting impression – even if it pours with rain amid a heatwave, like it did for us.

_{This post may contain affiliate links which means that I may earn a small commission, at no extra cost to you, for qualifying purchases. For more information, read our disclaimer.}   

No time to read about how to spend a weekend in Chester now? PIN THIS for later!

Day 1 in Chester – Saturday 

Walking the Chester City Walls

Chester is the only city to retain the full circuit of its ancient defensive walls, which stretch around 2 miles. Now, I’m not really one for historical walking tours, but Chester’s city walls are different. 

They’re intact, scenic and form a complete loop around the city, unlike the more fragmented walls you’ll find in York. It’s one of those things you have to do that makes a weekend break in Chester feel just a little bit more authentic.

There are four gateways to access the walls; Northgate, Eastgate, Watergate and Bridgegate, as well as many other steps you will come across dotted around the city. 

You can walk the complete circuit admiring the wonderful views to the city below including the Roman Amphitheatre, Chester Castle, Chester Racecourse, Chester Cathedral, Eastgate Clock and more.

Roman foundations, medieval towers, Victorian architecture – it’s all there. And the best part is that you can literally see the city unfolding from every angle. It’s like a 360° history lesson in the fresh air, with zero stuffy museums. 

Roman Amphitheatre 

You can see the ruins of Chester’s Roman Amphitheatre on the edge of Grosvenor Park from the city walls. It was built in the late first century to entertain around 7000 visitors with gory gladiator contests.

While it is the largest Roman amphitheatre in Britain, I have to say it was really underwhelming to visit. We noticed many school trips while we were there, groups of children given a guided experience with their very own Roman soldier, which was no doubt pretty exciting for them.

Eastgate Clock

You can’t miss the ornate Eastgate Clock when walking the city walls, this is what Chester is known for – alongside the cathedral. The clock is England’s second-most-photographed clock after Big Ben and was built to celebrate Queen Victoria’s diamond jubilee.

There are steps to either side of the clock if you want to walk down from the walls and photograph the clock from a different angle too.

Grab a coffee at Jaunty Goat

If you exit the city walls at Northgate, I highly recommend grabbing a coffee and resting your legs at Jaunty Goat. I visited their branch on Bridge Street and can confirm that their coffee is delicious. 

They have an extensive selection of locally sourced and freshly made food and bakery items, many of which are plant-based. I just wasn’t hungry enough to try anything sadly.

Get lost in The Rows

You can’t visit Chester without exploring The Rows. The medieval covered walkways on the black-and-white timber buildings full of shops above the ones at street level are unique to Chester.

Located on the four main streets in the city; Foregate Street, Watergate Street, Bridge Street and Northgate Street – you can’t miss them.

I stumbled upon these by accident when navigating to a restaurant for lunch and can confirm that they are a photographer’s delight. It’s well worth spending some time wandering around, there are some delightful independent jewellery shops, boutiques, book stores, a cheese shop, galleries and a cute little spot to paint pottery in. 

The idyllic spot for some retail therapy and a mooch. 

Lunch at Shrub

Every so often, I stumble across a restaurant that makes me think “I’d come back to this city just to eat here again” – and for me, Shrub was that place. Tucked away on Eastgate Row, it’s a stylish eatery and bar serving up exceptional plant-based food, alongside great coffee and cocktails. Think modern café culture in the heart of Chester – with warm, attentive service to match.

We went for a selection of small plates to share, washed down with my signature Aperol Spritz. Frickles (yes, deep-fried battered pickles, and they were glorious), teriyaki tofu, barbecued broccoli, and artichoke wings. Everything was delicious, but the wings completely stole the show.

Now, we’ve all seen cauliflower wings on menus – they can be hit or miss, right? Sometimes soggy, sometimes greasy. But artichoke wings? I’d never even heard of them. It’s one of those veggies I love but never really know what to do with – usually ends up on a pizza or tossed in a salad. Shrub turned them into something bold, crispy, and unbelievably tasty. So good, in fact, we ordered a second portion even though we were already full.

If you’re in Chester for the day, I highly recommend stopping by Shrub for lunch. The food is fantastic, the vibe is spot-on, and the view from the Chester Rows over the street below adds a lovely little bonus to the whole experience.

Chester Cathedral

After lunch, you can visit Chester’s most imposing building; Chester Cathedral. Founded as a Benedictine abbey in 1092, it is now a beautiful gothic style cathedral as of 1250.

While the cathedral itself is free to enter (donations are always welcome), they do charge an entrance fee in the summer and at Christmas which I personally thought was pretty steep. 

You can purchase a ticket to climb up the cathedral tower, where you’ll get one of the best views of the city. If you’re into history, you can book the Chester Cathedral at Height Tour and other Chester Cathedral tours that include Gothic architecture and stained-glass tours. Most tours start at 11am, so check this before you book.

Chester Market

Chester market is a short walk away from the cathedral and a bit of a hidden gem, if you ask me. I hadn’t seen anybody else mention it and so I wasn’t sure what to expect.

The market offers a vibrant selection of local goods, together with a fantastic choice of food stalls. Their premise was to create a modern traditional market in a welcoming and inclusive way for everyone, where you can shop local and eat global – and they’ve done that really well in my opinion.

They have everything from an organic butchers, florists, an Asian supermarket, food stalls, an art deco cocktail bar and more. One of the traders even sells the infamous Cheshire Farm ice cream, which I was told is a must-try when visiting Chester.

I can confirm this was delicious.

Every detail at Chester Market has clearly been well thought out, from the interior design to the selection of vendors. They have also kept sustainability in mind, incorporating features that benefit the planet, community, and local economy, such as these quirky and fun water refill stations.

Stroll along the River Dee

By late afternoon, I wouldn’t be surprised if you’re ready to slow things down and The River Dee is perfect for that. On the bank of the river is the ‘Groves’, a paved promenade complete with bandstand, cafés, restaurants and pubs.

There are kayaks for hire and if the weather isn’t atrocious like it was when we visited, you can book a 30 minute or 2 hour sightseeing cruise along the River Dee with a family owned company. Explore the stunning views of the city’s landmarks, including the Roman Walls, and the Old Dee Bridge, while cruising down the River Dee while learning about the points of interest on the cruise.

The cruises seem like a lovely way to end your first day in Chester, while resting your weary feet and dreaming of living in one of the beautiful riverside homes. 

Head to Pink Lettuce for dinner if you’re looking for some delicious vegan fare.

Day 2 in Chester – Sunday

You have two options here to choose how you prefer to spend your Sunday in Chester – and both of them are a short drive outside of the city. At a push, you could maybe do both on one day, but I would advise against that because you might be rushed.

Chester Zoo 

You can choose to visit Chester Zoo, one of the largest zoos in the country. The only downside of this is certainly the price – around £38 per adult and £28 per children between the ages of 3 and 15.

Chester Zoo is one of the main tourist attractions in the Chester, that is a 10 minute drive outside of the city. It is the perfect place to visit for half a day if you’re here with your family or children – but this was not for us.

The zoo focuses on conserving endangered species and keeping the environment as natural as possible. With over 37000 animals from over 500 incredible species, there’s a lot to discover here and I imagine it is a great day out if you have any little ones in tow. 

Cheshire Oaks Designer Outlet

Chester is also known for its outlet shopping at Cheshire Oaks, just a short 15–20 minute drive north of the city. If you’re in the mood for a bit of retail therapy, you could easily spend your entire Sunday browsing here.

What I really liked about Cheshire Oaks is that it leans more toward high street favourites than luxury designer labels. Sure, there are a few big names dotted around, but unlike places like Bicester Village, most of the shops feel actually affordable for the average person – which is kind of refreshing, right?

We ended up spending half a day there before jumping back on the motorway to embark on our four-hour road trip home to London! 

A weekend away in Chester is enough to get a good feel of its charm. The city reminded me so much of the weekend we spent in York, but on a much smaller scale. 

Whether you’re visiting for the history, the shopping or just to wander around somewhere pretty, a weekend break in Chester delivers.

Things to know before visiting Chester

Best time of year to visit Chester

UK weather as we know is extremely unpredictable – even more so the further north you go. Spring and summer are the best times to visit Chester, ideally between April and September. The weather is milder and there’s a slightly better chance of dodging the rain – though don’t quote me on that. A completely dry forecast in England is never a sure thing.

We were in the midst of a full-blown heatwave when we decided to take this detour. Temperatures had been above 35 degrees celsius in Manchester, so we thought we’d make the most of it and treat ourselves to an air-conditioned hotel room.

Naturally, as soon as we arrived in Chester, the temperature dropped, the rain rolled in (torrential at times), and we never did figure out how to use the air con in the room after all.

Chester can get pretty busy, especially on weekends, thanks to its popularity with hen parties and weekenders. If you’re hoping for a quieter experience, a midweek visit is your best bet – slightly fewer crowds (though it is a very destination with the elderly), more space to explore, potentially more affordable hotel rooms and a much calmer vibe overall.

How to get to Chester

Getting to Chester is pretty straightforward, whether you’re coming by train, car, or even bus. 

By car: Chester is well-connected via the M56 and M53, with plenty of parking options in and around the city centre. I always find driving around the UK to be the most convenient as our trains are not exactly reputable for their affordability or even reliability. 

By train: From London, direct trains from Euston take just over two hours. Trains from Manchester or Liverpool are both under an hour. 

By bus: This is an option I would personally never choose, however, Chester is well served by both National Express and FlixBus, with frequent services from London and other major UK cities. A coach ride from London takes around 4 hours and 45 minutes to 5.5 hours. Bus fares do start from around £15 though, if you book ahead.

By plane: Chester doesn’t have an airport, but you can fly to Liverpool John Lennon Airport or Manchester Airport. From which you can either get a bus or a train to Chester.

Where to stay in Chester

Hotel Indigo Chester would have ideally been my top pick; a contemporary boutique hotel that is located just outside the city walls, within walking distance of almost everywhere. 

The Hotel Chester would have been a close second for a real luxury stay in Chester, and an even swankier option would be The Chester Grosvenor right in the heart of Chester. Both hotels are plush 5 star luxury properties.

We, however, stayed at the DoubleTree By Hilton Hotel & Spa Chester, a short 20 minute drive away from the city itself. For some reason, hotel prices were incredibly high during the time we visited, and we knew that we were only really spending one day in Chester itself, so it made sense to stay somewhere just outside of the city and just pay for parking in the city for the day.

The hotel was everything you would expect from a comfortable Doubletree property, with nothing extraordinary. The rooms were clean and spacious – space being something that may not be a given with a city centre hotel. 

While we didn’t make use if the pool or spa facilities during our stay, the service throughout was very friendly.

Breakfast was included as part of our stay and delightful – always remember to ask for veggie sausages at a Hilton breakfast buffet. They don’t always have a sign displayed to remind you, but they have always provided them at every Hilton Doubletree I have stayed at.

If you’re looking for an affordable luxury stay near Chester, then the Hilton DoubleTree Hotel Chester would be a great choice.

How To Get Around Chester

One of the best things about Chester is how walkable it is. The main sights, shops and restaurants are all clustered within the historic city centre, so you can easily explore on foot without needing to use any public transport. 

If you’re heading a bit further out to Chester Zoo or Cheshire Oaks, there are regular local buses and plenty of taxis or Ubers available. But for the most part, comfy shoes and a sense of curiosity are really all you need.

If you enjoyed this guide to a weekend break in Chester , PIN IT for later!

Looking for more UK weekend break inspiration?

• How To Spend 2 Days In The Cotswolds Itinerary
• How To Plan A 3 Day Northern Ireland Road Trip To The Giants Causeway
• How To Spend A Weekend In York: The Perfect 2 Day Itinerary
• The Perfect Winter Staycation At Bournemouth Beach Lodges
• Planning The Ultimate Stag Weekend In Edinburgh