Chester Weekend Break | 2 Day Chester Itinerary

Chester is a picturesque city in Cheshire on the River Dee. It was founded by the Romans in AD 79, and the city played an important role in Britain’s early history. It became a major centre for trade and commerce during the Middle Ages and was later an important military stronghold during times of conflict.

Located on the English-Welsh border, Chester is a charming cathedral city perfect for exploring Roman history, expanding your knowledge in the many museums, and enjoying the extensive shopping and dining out.

This travel guide to your Chester weekend break will help you plan your 2 day itinerary including the best things to see in Chester, top places to eat, and where to stay.

Where to stay in Chester

Being the home to the racecourse, the gateway to Wales, bags of heritage, and great shopping, a Chester weekend break is a popular choice. These best hotels in Chester have been selected for their sustainable policies, personal experience and top ratings.

Hotel Indigo Chester is definitely my top pick in the city. This boutique hotel is located just outside the city walls, and they prove you can have a sustainable, luxurious, comfortable, and friendly space all rolled into one! The dinner at The Forge was simply delicious too! > CHECK THE LATEST PRICES AT HOTEL INDIGO CHESTER

Moxy Hotel Chester is a Marriott property certified as LEED Gold for its green building design. The room was comfortable with a cool decor and the ”Plug and Meet” communal areas have a stylish funky design too. Unfortunately, the bar food was a little bland but there are lots of well-reviewed pubs by the canal if you want to try. > CHECK THE LATEST PRICES AT MOXY HOTEL CHESTER

YHA Chester Trafford Hall is located outside of the city in Dunham-on-the-Hill, in a glorious Georgian house with 14 acres of grounds. YHA is a social enterprise, that offers incredible value for money. Whilst I have not stayed in this one, I have stayed in many YHA and can recommend if visitors are on a budget. > CHECK THE LATEST PRICES AT YHA CHESTER TRAFFORD HALL

What to do on a Chester weekend break

Photograph the Eastgate Clock

As you pass under the bridge into the City of Chester, take a moment to admire the Eastgate Clock, which is said to be the most photographed clock in England after Big Ben. But that is not the only reason why the Eastgate Clock is Chester’s most iconic landmark.

The Eastgate, a Grade I listed building, was constructed in 1768 replacing the original Roman gates and forming the main entrance to the city. The turret clock was added in 1899 to celebrate Queen Victoria’s Diamond Jubilee.

Take a tour with a Roman soldier

An award-winning tour with a Roman soldier in Chester is an engaging and educational experience that brings the city’s rich history to life, providing insight into the lives of Roman soldiers and civilians.

Starting at the Town Hall, you are asked to imagine the layout of the stronghold of Chester with the help of a drawing, then taken to hidden ruins under the high street shops.

We walked along Chester city walls learning about the role they played in the city’s defence, then visited the Roman Gardens which house the remains of local Roman sites including columns, carved fascias, and a reconstructed hypocaust (underfloor heating system) that have been discovered at various locations around the town and reassembled here.

Close by is the Roman amphitheatre, which was built in the 1st century AD, and is the largest in Britain. The soldier explains the games and battles that took place there.

Roman Tours happen daily at noon and 3 pm

See the fresco in St John the Baptist’s Church

St John the Baptist’s Church, located between the Roman amphitheatre and River Dee, is the oldest church in Chester. It was first founded on an early Christian site in the late 7th Century by King Aethelred of Mercia and St Wilfred of Ripon and has undergone numerous transformations over the centuries encompassing Romanesque, Gothic, and Victorian architectural styles.

The church houses a range of treasures, including a collection of historic effigies and brasses, a 14th-century font, as well as a stunning fresco that dates back to the 13th century.

The fresco, which is located on the north wall of the nave, depicts the life of St. John the Baptist, from his birth to his martyrdom. This medieval art is considered one of the church’s most important treasures. It reminded me of the painting of John the Baptist found in Shakespeare’s Schoolroom in Stratford-Upon-Avon.

St John the Baptist’s Church is open daily, and free to enter (donations welcomed).

Sick To Death Museum

Sick To Death offers a fascinating look at the history of medicine and healthcare, with exhibits covering topics such as surgery, public health, and mental health- it’s a fun museum to visit on your Chester weekend break!

There are fun interactive displays, historical artefacts, and informative exhibits that showcase the evolution of medical practices and technology. Hear how the physician Galen was diagnosing disease from urine samples 4000 years ago, the history of the Miasma theory, the Great Plague doctors, women in surgery, STD, and the potions that did not work, including Trump’s ridiculous treatment of ingesting disinfectant to cure Coronavirus.

Sick To Death is open daily from 10 am – 6 pm. Entry is £7 for adults.

Deva Roman Discovery Centre

Deva Roman Discovery Centre houses reconstructed rooms and exhibits showcasing the daily lives of Roman soldiers and civilians. The museum also features a 3D film presentation that transports visitors back in time to experience life in the Roman Empire.

Our guide, dressed as a Roman character, was an archaeologist that unearthed the ruins and trenches displaying the layers in the soil which relate to historical occupation and events from Roman-Saxon times through to the Post-Medieval era. I loved hearing so much knowledge delivered with passion making this a fascinating tour.

Deva Roman Discovery Centre is open on weekends from 10.30 am – 4.30 pm (daily in school holidays). Entry is £8 for adults.

Visit the Grosvenor Museum

First opened in 1886, the Grosvenor Museum was built to house the collections of the Chester Archaeological Society and the Chester Society of Natural Science, Literature, and Art.

Today, it continues to offer a thought-provoking look at the history and heritage of Chester. The interactive displays, archaeology, Roman tombstones, fine art, and informative exhibits showcase the city’s development over time. It’s a lovely museum worth a visit.

Grosvenor Museum is open Tuesday – Sunday, and is free to enter.

Visit the Cheshire Military Museum

The Cheshire Military Museum is an independent museum located within Chester Castle, which follows the Cheshire’s military units, including the Cheshire Regiment and the Cheshire Yeomanry. through time from the 17th century to the present day. The museum’s collection includes weapons, uniforms, medals, and other artefacts.

The museum narrates the travels of the Cheshire Regiments across the world during many great battles and conflicts with exhibits covering a range of conflicts, including the First and Second World Wars, the Boer War, the Burma War, the Korean War and the Napoleonic Wars, to name but a few.

Cheshire Military Museum is £4 to enter. Open from Thurs-Sunday 11 am – 4 pm.

Climb the tower of Chester Cathedral

Chester Cathedral was originally built as a Benedictine monastery in 1092 and later became the Cathedral of the Diocese of Chester in 1541. The cathedral began in the Norman style of architecture and was rebuilt in 1250 in the Gothic style.

The cathedral survived some turbulent times as Henry VII dissolved the Benedictine Abbey in 1514, and was damaged by Puritan vandals during Cromwell’s time.

Climb the spiral staircase to see Chester Cathedral from a different perspective. Each level comes with entertaining anecdotes, medieval stories, and quirky architectural facts spanning 900 years. If you love geeking out on English history and cracking views, give the Chester Cathedral at Height Tour a go!

Chester Cathedral is free to enter (donations welcome). The Chester Cathedral at Height Tour costs £14, and there is a list of other Chester Cathedral tours from storytelling, Gothic architecture, and stained-glass.

Explore the Chester Rows

The Rows of Chester is a distinctive system of buildings lining the four main streets of the Chester radiating out from the Cross. The buildings are linked by walkways on the first storey, effectively creating a second street level.

The layout of the Rows goes back to the 13th century, and there are many theories as to why they were built. One theory is that they were constructed on top of the debris remaining from Roman times, to avoid the sewage that was emptied from the upper levels onto the street, or for security against Welsh raiders.

Whatever the reason for their creation, The Chester Rows and many of their buildings are listed and stand in a designated Area of Archaeological Importance.

The half-timbered galleries, accessible by steps, are lined with cafes and shops and are popular for tourists to explore. Take the audio tour to learn more about The Chester Rows.

Take a Chester Boat Cruise

Taking a Chester Boat Cruise departs from The Groves and is a great way to experience the charming city 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. The informative commentary from the captain gives you the background on points of interest on the cruise.

The Half-hour City Cruise is a lovely experience to rest your weary feet, feel the sun on your face and dream of living in one of the beautiful riverside homes.

If your itinerary allows and you love a spot of bird-watching, you could try the Two-hour Iron Bridge Cruise through the Duke of Westminster’s Eaton Estate.

ChesterBoat operates daily, with themed and sightseeing cruises. Check reviews on Tripadvisor.

Kayaking on the River Dee

Kayaking on the River Dee is a popular activity for visitors to Chester, and the perfect way for adventurers to explore the city and its natural beauty. The river, which flows through the city and out to the Irish Sea, has tranquil waters, stunning scenery, and rich history.

Whether you’re a seasoned kayaker or SUP-lover, a trip down the River Dee is an unmissable experience. If you want a bit more action, you can go upstream to Llangollen to take on the rapids in the Dee Valley. This is top of my list for my next visit!

Dee River Kayaking offers guided tours and equipment rental, making it easy for everyone to enjoy these thrilling activities. Check the reviews on Tripadvisor.

Chester Castle: Agricola Tower

Chester Castle was built by William the Conqueror in 1070 and became the administrative centre of the Earldom of Chester. Over the centuries, the castle was used as a military barracks, a courthouse, and a prison, and it played a crucial role in the defence of the city during times of conflict.

The Agricola Tower was the first stone gateway to Chester Castle and is one of the most recognisable structures of the castle. The top floor of the three-storey tower is the Norman chapel of St Mary de Castro, where the guides will show you the fine wall paintings and frescos dating from 1240.

Chester Castle opens on special occasions and is free to enter.

Top places to eat in Chester

Best coffee shops

Jaunty Goat is an independently owned plant-based coffee shop that focuses on sustainability and supplying a high-quality carbon-neutral roast. Jaunty Goat is located on Northgate St + Bridge St.

Flower Cup serves tasty ethically sourced specialty coffee, and all-day brunch, set amongst a flowery décor to bring a fresh feel to your day. Flower Cup is located on the Watergate Row.

Best restaurants in Chester

The Forge is an elegant brasserie with an open kitchen and dining experience by restaurateur and chef Mike Robinson. Sustainability and British ingredients are in their DNA, and the seasonal menu is top-class. The Forge is located in Hotel Indigo Chester.

Shrub Chester oozes café culture vibes. The global menu is plant-based cuisine, cocktails and coffee. The pumpkin tortellini just melted in my mouth. Shrub Chester is located in Eastgate Row.

FAQs for visiting Chester

How to reach Chester by train?

There are direct trains from local stations such as Birkenhead Central, Liverpool Lime Street, Liverpool Central, Liverpool James Street, and Warrington Bank Quay. It is possible to travel from London and Manchester on direct trains. The station is an approximately 15-minute walk from Chester city centre. > CHECK TRAIN TIMES

What is the best time to visit Chester?

This is UK weather we are dealing with so it can be unpredictable. The most pleasant and best months to visit Chester are June through August. As always, travelling in the low season will give you better prices in hotels so to catch moderate weather you may wish to go for spring or autumn. I visited in April and was blessed with a hot day and a rainy day so I planned my activities around this.

Are there any festivals and events in Chester?

If you are visiting Chester for festivals, there is something for everyone, at all times of the year. With CarFest, Dev Fest, Chester Literature Festival, Chester Folk Festival, Boodles May Festival, Cheshire Food Festival, Chester Craft Beer Festival, Chester Pride, and Chester Heritage Festival. Need I go on?

Is Chester worth visiting?

Chester is a great place for a day trip or a lovely weekend away. The heart of the city is brimming with heritage, pretty parks, riverside walks, wonderful shops, museums, and places to eat making this a perfect Chester weekend break.