We recently spent two days exploring the city; it was my first trip to Chester, and the city didn’t disappoint. Whether you’re fascinated by history, looking for family-friendly activities, or simply want to soak up the atmosphere. Chester offers something for everyone. Here’s a guide to the best things to see and do in this historic city and how we spent our time exploring.

Chester is one of England’s most picturesque cities, steeped in history and brimming with charm. From its well-preserved Roman walls and medieval half-timbered buildings to its unique shopping galleries and scenic riverside, there’s plenty to explore.

If you’d like a post on what to do in Chester when it rains, check out this post here!

Where to Stay In Chester

We stayed at Hotel Indigo, a charming boutique hotel just outside the city walls, only a 5-minute walk into the centre of Chester. With its luxury feel, spacious rooms, and stylish décor, it provided the perfect base for our stay.

The hotel is also conveniently located near a car park, making it easy to unload bags, check in, and start exploring. One of the highlights was the wonderful steak restaurant, offering a delicious dining experience in a warm and inviting setting.

Things To See And Do In Chester

Founded as the Roman fortress of Deva Victrix in AD 79, Chester played a crucial role in the Roman occupation of Britain. Today, visitors can still see remnants of this past, including the Roman Amphitheatre, once the largest in Britain. Plus, the city walls offer a scenic 2-mile walk around the city.

During the medieval period, Chester flourished as a market town. It’s unique “Rows”, two-tiered covered shopping galleries, date back to the 13th century. These distinctive black-and-white timbered buildings house shops, cafés, and boutiques. Thus creating an atmospheric shopping experience unlike anywhere else I have experienced in the UK.

Walk the Roman City Walls

Walking Chester’s city walls is one of the best ways to experience the city’s rich history while enjoying fantastic views. At just under 2 miles (3.2 km) in length, the walls form the most complete circuit of Roman and medieval defensive walls in Britain. The full loop took us just over 40 minutes; there are so many interesting stops along the way to find out more about the history of Chester. Not all of it is scenic, but most of it is. And it’s a great way to get your bearings and enjoy the city. Points of interest along the way include…..

Eastgate

The gateway to the city’s central shopping area, was built in 1768. It is an arched structure that supports the walkway of Chester’s city walls. We started our walk at Eastgate at Chester’s most iconic landmark, the Eastgate Clock. Built in 1899 to mark Queen Victoria’s Diamond Jubilee in 1897. It is said to be the second-most photographed clock in England after Big Ben.

The Roman Gardens & Amphitheatre 

The Roman Gardens and Amphitheatre in Chester provide a glimpse into the city’s Roman heritage. The gardens, located near the city walls, feature ancient Roman columns, mosaics, and inscriptions. Therefore recreating the public garden spaces of Roman times. Adjacent to the gardens is the Roman Amphitheatre, the largest in Britain, dating back to the 1st century AD.

Once used for gladiatorial combat and military training and displays, it could hold in excess of of 8,000 spectators. Today, both sites are free to visit and offer an immersive experience into Chester’s fascinating Roman past.

King Charles’ Tower 

Otherwise known as the Pheonix Tower. This tower, on the north section of the walls, is where King Charles I reportedly stood in 1645 to watch his army being defeated during the English Civil War. Today, it offers excellent views over the city.

Chester Castle

Chester Castle is one of the most important historical landmarks in the city, offering a fascinating insight into Chester’s role in England’s medieval and military history. Originally built by William the Conqueror in 1070 as part of his conquest of England, the castle has undergone significant changes over the centuries, serving various roles, including as a royal fortress, prison, and administrative centre.

Watergate and the Racecourse 

Near Watergate, you’ll get a fantastic view of Chester Racecourse, which is said to be the oldest racecourse in Britain, dating back to 1539.

Pemberton’s Tower

 Is a 16th-century tower located along Chester’s city walls, built during the reign of Queen Anne. Offering a strategic lookout point for the city. While not as famous as other landmarks, I think it’s one of the prettiest on the walls. Visitors can view the tower from the city walls, making it a quieter, less touristy spot to explore.

Visit Chester Cathedral 

One thing you can’t miss on a trip to Chester is the cathedral. Entry is free, although donations are welcomed. Allow some time to take in the grandeur of the cathedral and its craftsmanship; it truly is breathtaking. I recommend taking time to visit when the organist is playing as it’s magical to experience the halls fill with music.

This is a breathtaking Gothic cathedral with stunning stained glass, medieval carvings, and a tranquil cloister garden. Boasting a history that stretches back over a thousand years. Initially founded in the eighth century. The site has witnessed the rise and fall of empires, which feels quite mindblowing as you stand in front of the majestic eagle.

From its roots as a Roman fortress to the establishment of a Benedictine monastery by Hugh of Avranches in 1092. It wasn’t until the Dissolution of the Monasteries in 1541 that Chester’s cathedral became the iconic building we see today.

Explore The Rows

I think you have to see the Rows to fully appreciate their charm. The Chester Rows, dating back to the 13th century, are one of the city’s most iconic features. Offering a unique combination of medieval history and modern shopping. These two-tiered arcades are found along Eastgate Street, Bridge Street, Watergate Street, and Northgate Street.

The rows feature a sheltered upper level with boutiques and shops accessed by staircases, while the lower level hosts traditional shops, cafes, and restaurants. Built on medieval foundations, many of the buildings date back to the 14th and 15th centuries, though they’ve been updated and restored over time, making the Chester Rows a fascinating glimpse into Chester’s rich past while providing a vibrant shopping experience.

Stroll Along the River Dee 

The River Dee has played an integral role in Chester’s development, serving as a vital trade route and defensive boundary throughout the ages. In Roman times, the river was crucial for transporting goods and military supplies, contributing to Chester’s importance as a Roman fortress. The Dee also formed part of the city’s defensive line.

Today, the River Dee remains a central feature of Chester, offering visitors both a peaceful retreat and a glimpse into the city’s vibrant past. Whether you’re walking along the river, enjoying a boat ride, or simply soaking in the views.

Check Out The Storyhouse In Chester 

The Storyouse is an incredible cultural hub, combining a theatre, cinema, library, and café, with a packed programme of events. I am a huge theatre and book fan so this is a space I would use all the time if I was local. And if you are travelling with kids check out the kiddies library its adorable.

Visit Chester Market

We loved Chester Market. It’s more than just a shopping destination; it’s a beautiful space, full of street food and cocktail options and artisan stalls by local traders. Also, check out the statue of The Chester Market Boar, inspired by the Romans. The market is located directly above the barracks of the XX Legion, who built Chester. And their symbol was a wild boar.

Cute Things To Look Out For In Chester

The Painted BT Cabinets

The Painted BT Cabinets in Chester are a quirky and artistic feature that have become an unexpected part of the city’s cultural landscape. These are a series of BT telephone boxes that have been transformed into colourful works of art painted by various artists. Found across Chester, these cabinets serve as a public art installation, blending the city’s historical charm with a modern creative touch.

The Chester Mini Murals

We never had time to complete this, but the Chester Mini Murals are a fabulous collection of small, vibrant murals located throughout the city. This is perfect for families or if you love a city hunt. Adding a burst of creativity to Chester’s urban landscape. These artworks can be found on hidden walls, alleys, and buildings, creating a unique visual trail for those willing to explore beyond the main tourist attractions. Just scan the QR code and off you go.

Find Janya the Little Elephant 

Created by Annette Yarrow in 2010 this gorgeous bronze sculpture is a gift from Chester Zoo to the people of Chester. She can be found on Northgate Street and is adorable.

Why Chester is Perfect for Couples and Families

Chester is a city that effortlessly blends history, culture, and charm, making it a fantastic destination for both couples and families. Whether you’re strolling along the Roman walls, discovering hidden mini murals, or enjoying a leisurely boat ride on the River Dee, there’s something special for everyone.

For couples, Chester offers a romantic escape with its quaint streets, cosy cafés, and rich heritage, perfect for a weekend getaway. Families, on the other hand, will find plenty of engaging attractions, from the iconic Rows to interactive experiences at Chester Zoo or Storyhouse.