Phil and Garth > Destinations > Europe > UK > England > Medieval Chester Things To Do In 1 Day

Medieval Chester Things To Do In 1 Day

by Garth

Last updated: 24th October 2021

Chester in North West England is the perfect place for a city break full of old world English charm. Chester is ideal because of its compact size, you can squeeze a lot into a day like sightseeing and shopping which is what we did. In this travel guide we’ll show you the best Chester things to do in 1 day.


About Medieval Chester

Chester is a charming medieval city in the North of England. Founded by the Romans they built a fort called Deva in 79AD, to protect the land from marauding Welsh and English tribes. But it’s as a medieval city Chester is best known, full of lovely Tudor black and white half timbered buildings. It also has Britain’s best preserved city wall, other British cities have torn theirs down for expansion. Located on the River Dee, Chester used to be an important trading town during the medieval period when the town flourished, but by the end of the 15th century the River Dee silted up, and the Port of Chester went into decline, benefiting nearby Liverpool.

View of historic Eastgate, a bustling shopping area

View of historic Eastgate, a bustling shopping area



Chester Things To Do

The City Walls

Chester’s City Walls were first built by the Romans in 79 AD originally in wood and later rebuilt in stone. After the Romans abandoned the city in the 5th century the Saxons strengthened the wall during the 10th century (the medieval period). By the 1500s the wall had watchtowers, but during the Civil War it took a battering from cannon balls which destroyed portions. The wall was repaired in the 18th century and changed to a walkway for the Victorians to stroll which is exactly how they are today.  We walked the 2 mile stretch of the distinct rose coloured sandstone walls which circle the city.

Chester City Wall with water tower in the distance

Chester City Wall with water tower in the distance

To access the wall we climbed the steps at The Eastgate Arch. There are steps at all four of the original gateways into the city, today the gates have long gone, and since replaced with arches. As for the other three gates, ‘Northgate’ is a Georgian arch which replaced the original Roman gateway in 1810. ‘Newgate’ was rebuilt in 1937, and ‘Wolfgate’ dates back to the 12th century.

You can’t miss Chester’s iconic clock here – The Eastgate Clock. We liked the ornate ironwork it’s very fancy. It was made for Queen Victoria’s Diamond Jubilee in 1897 and is considered by Chester to be the 2nd most photographed clock in England after Big Ben in London, really?! we didn’t know that. It was also a good place to people watch below.

Chester's Eastgate Arch

Chester’s Eastgate Arch

The ornate Eastgate Clock

The ornate Eastgate Clock

The city wall as seen from The Roman Gardens

The city wall as seen from The Roman Gardens

Garth on Chester's city wall near the River Dee

Garth on Chester’s city wall near the River Dee

Our leisurely stroll along the length of the wall took us about 50 minutes. We picked up a free walking guide from the tourist information office beforehand, but didn’t really need it as there were lots of handy plaques along the way to explain different parts you’re looking at.

We passed Chester Racecourse, Britain’s oldest racecourse where horse racing started back in 1539. Racing events are really popular with groups of young people who get really dressed up, like a school prom, it’s a big day out.

Britain's oldest racecourse

Britain’s oldest racecourse

Canal boats in Chester

Canal boats in Chester

We also watched people manoeuvring their canal boats along the stretch of the canal that runs alongside the wall.  There was also another spot on the wall with a view across to the Welsh mountains in the distance.

Look out for the Grosvenor family’s symbol in brick patterns. These diamond shapes signify the building belongs to the Grosvenor Estate owned by The Duke of Westminster.  The wealthy family own huge amounts of property across Cheshire, Oxford and London’s Mayfair and Belgravia.

Look up to see the Grosvenor family brickwork symbol

Look up to see the Grosvenor family brickwork symbol



Chester’s Unique Shopping ‘Rows’

Looking like something straight from a Harry Potter movie are the Tudor buildings on the 4 main shopping streets of Chester – Northgate, Eastgate, Bridge and Watergate Street. They lead out from the Market Lantern Cross from 1476 which was once the focal point of the city. All 4 streets are lined with ‘The Rows’ and are unique to Chester, and the world! These Tudor style double decker buildings are really handsome and date back to the 13th century and are also called ‘galleries’ – basically two storied shopping arcades.

The Market Lantern Cross in the foreground with Chester's unique Rows in the background

The Market Lantern Cross in the foreground with Chester’s unique Rows in the background

The classy Grosvenor Shopping Centre

The classy Grosvenor Shopping Centre

Chester's Rows - two tiered shopping arcades

Chester’s Rows – two tiered shopping arcades

The shops are typical of any other high street, but Watergate and Lower Bridge Street seemed to have more independent shops. If you like nice department stores try Browns of Chester (Debenhams) which has been there for years.

Phil striking a pose on The Rows

Phil striking a pose on The Rows

We thought the Rows are the perfect example of a medieval shopping mall! On Bridge Street look for ‘Three Old Arches’ it’s the oldest section of The Rows and original from the 13th century. It’s also considered to be the oldest shopfront in Britain.

Three Old Arches - The oldest shopfront in Chester

Three Old Arches – The oldest shopfront in Chester

Chester's handsome tudor buildings

Chester’s handsome tudor buildings

But surprisingly many of the Tudor buildings you see could be described as mock Tudor. The Victorian’s brought wealth to Chester with the industrial revolution and they restored buildings to their former glory, how’s that for early restoration!  Either way buildings stand as splendid examples of both Tudor and Victorian architecture.

The black and white colour palette is everywhere!

The black and white colour palette is everywhere!



Afternoon Tea Party

Have a cream tea, or afternoon tea like we did at Mad Hatters a lovely tearoom and bakery. Mmm, it was fab! Look out for the quirky doorstop on the way out!

Have an English afternoon tea

Have an English afternoon tea



Roman Basement

This is our bizarre tip – Get a free view of a perfectly preserved Roman hypocaust in situ. It was an original form of underfloor heating and it’s in the basement of Spud-u-Like on Bridge Street, we cheekily wandered down their steps without eating there, but nobody seemed to mind.

A real Roman Hypocaust in the basement of Spud-u-Like

A real Roman Hypocaust in the basement of Spud-u-Like

You can poke your head right inside this Roman hypocaust

You can poke your head right inside this Roman hypocaust



Roman Amphitheatre

Off Newgate, just outside the wall are the remains of a Roman amphitheatre built in 86AD. Up to 7,000 people would have been spectators here. It was discovered in 1929 and is the largest ever found in Britain. Only part of it has been excavated so there’s not really much to see, so we used our imagination of gladiators having fights in the arena. However we did see a Roman Centurion!  …well some guy in a costume giving a history lesson to kids.

Chester's Roman amphitheatre

Chester’s Roman amphitheatre



Roman Gardens

Just over the road opposite the Amphitheatre were some Roman relics laid out in a small garden. It also houses a reconstructed ‘hypocaust’ using pieces found (the one in Spud-u-like was much better). There’s a clever illustration in these gardens of what the breach in the City Wall might have looked like in 1645 during The Civil War.

Chester's Roman Gardens

Chester’s Roman Gardens

Illustration of the breach in the City Wall

Illustration of the breach in the City Wall



The Nine Houses

We walked through the Roman Gardens and went through a rusty looking corridor through the City Wall at the end, which opened out onto a road with ‘The Nine Houses‘. Just look at the front doors, they’re like little hobbit houses, infact they were Almshouses built for poor elderly people in the 17th century. today there are only 6 of the 9 left. We’ve come across Almshouses a few times now in other medieval cities we’ve visited across the UK.

Garth at The Nine Houses - former almshouses

Garth at The Nine Houses – former almshouses



Chester Castle

If you walk the wall circuit you’ll come across Chester Castle, built in 1070. It looked quite modest in size compared to other castles in Britain.  We only saw it from the vantage point on the wall, so we’re pretty sure there was probably more to it than what we saw.

Chester Castle

Chester Castle



Chester Cathedral

Chester’s gothic style Cathedral is quite something. Construction began in the 10th century as an abbey church, and was modified over centuries. In 1540 it became Chester Cathedral. Unusually this cathedral had a free standing bell tower in the grounds.

Inside is monumental! we love gothic architecture, the work that must have gone into this place with all the intricate carving is just incredible. So sit down, admire and appreciate the creative work of our ancestors. It took an incredible 275 years to build! The stained glass looked great too with the sunlight streaming through. Even if you’re not religious it’s worth visiting for the sheer beauty. Phil pointed out to Garth the unique courtroom inside. We didn’t take the tour, just had a look around ourselves.

The exterior and gardens of Chester Cathedral

The exterior and gardens of Chester Cathedral

The magnificent interior of Chester Cathedral

The magnificent interior of Chester Cathedral



Really Old Pubs!

We found Chester’s oldest oak timber-framed building built in 1661. It’s now a pub, The Bear & Billet, and was once used as a toll gate into the city. It looks old and wobbly! really striking with its classic black and white Tudor styling, ye olde England at its best. Phil liked the cute little leaded glass windows, we learnt they had small windows because large panes of glass could not be produced in those days, and incase you were wondering about those colours, well the timber was painted in black tar and the white was lime wash.

Ye Olde Boot Inn is another, it’s also from the 17th century and still has it’s some of the original medieval seating. Both pubs are not modern day gastro-pubs, instead old fashioned, no-frills British boozers, so if you want to join the regulars, then head to either of these places.

Chesters oldest pub built in 1661 - The Bear and Billet

Chesters oldest pub built in 1661 – The Bear and Billet

Ye Old Boot Inn. established 1643

Ye Old Boot Inn. established 1643



The Groves

After taking in the city’s history and sights we headed down to the tranquil River Dee past the historic Old Dee bridge and on to The Groves – a delightful promenade beside the river for a walk.

We were tempted to have a go on the pedal rowing boats, but decided to keep walking and get ice-cream.  It was a lovely area especially on the summer day we had.  There were also short pleasure boat trips on offer here too.

The Queens Park suspension bridge had great views over the River Dee, a really picturesque spot and a great place for just watching the world go by like the swans and ducks. Over the bridge is The Meadows, a large park where families were having picnics.

The Groves - looking down the River Dee

The Groves – looking down the River Dee

One of Chester's landmarks - The Old Dee Bridge

One of Chester’s landmarks – The Old Dee Bridge

The Old Dee Bridge once had a drawbridge and towers

The Old Dee Bridge once had a drawbridge and towers

The Groves - A perfect place to relax on a summer's day

The Groves – A perfect place to relax on a summer’s day

Phil at the Queens Park suspension bridge

Phil at the Queens Park suspension bridge



Victorian Signs & Objects

We found an early Victorian postbox just outside the the Town Hall, you don’t see many of these early hexagonal pillar boxes, so Phil figured it was worth a photo opportunity!  Here’s a fact for your next pub quiz – Is it considered ‘an act of treason’ to place a stamp with the Queen’s head upside down on and envelope? … well a few years ago The Royal Mail finally gave an answer to an old English law, they said it’s not an offence, so there you go!

There’s also plenty of old Victorian signs around the city, look up and you’ll see examples etched or painted onto buildings. Garth is always on the lookout for these! If you’re into typography then you’ll understand why.

Phil at Chester's old penny postbox

Phil at Chester’s old penny postbox

Some lovely typography on these old Victorian signs in Chester

Some lovely typography on these old Victorian signs in Chester



Other Chester Things To Do & Attractions

  • Chester Zoo – Voted one the best in the world. (7th best on TripAdvisor).
  • Grosvenor Park – 20 acres in the city centre, good place for a walk, rest or to take the kids.
  • Grosvenor Museum – Roman artefacts and relics, plus watercolours by Louise Rayner.
  • Chester Military Museum – Celebrating Cheshire Regiment achievements. Housed in former barracks.
  • The Storyhouse – Go here in the evenings for theatre and pre show cocktails.
  • Chester Races – Is such a fun day out when a race is on and everyone gets glamed up.


Chester Practical Information & Useful Advice

Phil and Garth at Chester's iconic Eastgate Clock

Phil and Garth at Chester’s iconic Eastgate Clock

Phil and Garth’s Top 5 Chester Travel Tips

  • Tip #1: Parking is really expensive in Chester city centre, so we took the train..
  • Tip #2: Into the paranormal? Ghost Hunter tours are available from
  • Tip #3: If you’ve got kids, then look out for the entertaining Town Crier near The Market Lantern.
  • Tip #4: Looking for luxury? The Chester Grosvenor is the city’s 5 star hotel.
  • Tip #5: Take an umbrella with you, showers can happen anytime in England.


Chester FAQ

  • What’s the nearest airport to Chester? LPL – Liverpool John Lennon Airport is the nearest airport, 11 miles away.
  • What time zone is Chester? GMT +0. Greenwich Mean Time.
  • What currency is used in Chester? Pound Sterling (symbol: £)
  • What language is spoken in Chester? English.
  • What is the population of Chester? 118,200.
  • What number should I call in an emergency? Call 999.
  • What plug type is used in Chester? Plug Type G. Voltage is 240V / 50Hz.
  • When is the best time to visit Chester? March to October. Summer is peak season when it’s warm.
  • When is the worst time to visit Chester? November to February it’s cold, snowy or wet.
  • What is Chester famous for? Romans, Tudor buildings and shopping.
  • What’s the history of Chester? The city was founded by the Romans in 79AD.
  • What are the 5 must see sights? City Walls, Chester Cathedral, The Groves, Roman Gardens and The Rows.
  • What is the local food? Eat a Cheshire pork pie made with apples, butter and sweet spices.
  • What is the best way to get around Chester? Chester’s city centre is small enough to walk everywhere.
  • What’s a fun fact about Chester? Daniel Craig was born in Chester in 1968.
  • What tv shows have been filmed in Chester? The British tv soap Hollyoaks is filmed in Chester.
  • Where is the best photo spot? Next to the Market Lantern Cross.
  • Where is a hidden gem in Chester? Grosvenor Park.
  • What’s the best souvenir to buy in Chester? Cheshire cheese – a crumbly cheese produced in the county.


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Marcelle Simone Heller 27th September 2016 - 9:29 am

How could we miss out on Chester?! What a beautiful pictures! You really present the town in the best light. All these timber-framed houses are stunning.

Barry 26th September 2016 - 1:07 pm

Great write up guys. I grew up in Cheshire and as Chester is the capital I have wandered around many time in the day (& occasionally drunk at night). Even though I haven’t lived in the UK for over eight years now, I recognise most of the landmarks in your photos. Makes me a little homesick!

Vyjay 26th September 2016 - 1:44 am

Your article with the stunning pictures transported me back in time to a Chester of the medieval times. The place still retains much of its old charm including the City walls. This coupled with its natural beauty makes it really enticing for travelers.

Rob+Ann @TravelLatte(.net) 25th September 2016 - 11:53 pm

What a fantastic city! It’s charming places like Chester that make us sometimes wish we lived in the UK. I can just imagine the city in the Christmas season – it must be magical. We had never heard of Chester before, but it’s now firmly on our To Do list. Thanks for introducing us!

Travel Lexx 24th September 2016 - 7:37 pm

Again, I am ashamed to admit I haven’t been to Chester. My only experience was heading past on a National Express to and from Liverpool but it was at night so I didn’t get to see much. Such beautiful architecture and so much history! I genuinely didn’t realise how much remains from the Roman times. And the 1274 shopfront – that’s just amazing! Thanks for sharing!

Lisa 24th September 2016 - 8:46 am

Chester seems absolutely fun and a place I would love to visit. I love places with lots of unique history. The clock is beautiful along with the cathedral. The gardens and castle would be must visits. All around perfect place to go! Will save this post for future visit, thanks for sharing.

Jenn 23rd September 2016 - 11:32 pm

Another great post! I love the quality and clarity of your photos. The city wall peaking through the trees and growth is such a teaser for me! And, the Tudor buildings, gardens, and the cathedral! So many great looking things here! One day, I will enjoy a proper English tea party too! I love tea and can’t wait to experience it how you’ve highlighted here!

David 23rd September 2016 - 9:19 pm

I didn’t know Chester had Roman heritage and that makes me want to visit even more. Such beautiful architecture and so quintessentially English. I’m glad you shared this as it’s given me another places I need to visit on my eventual tour of Britain.

Stephanie (1AdventureTraveler) 23rd September 2016 - 5:12 pm

The medieval city of Chester in Northern England with it’s English Tudor buildings looks like such an amazing place to visit. I have never heard of Chester but would love to visit and especially do some trendy shopping. Chester with it’s walls built by the Romans, the Eastgate Clock, gardens, restaurants, zoo, and so much more to do there. The history of this English town is very interesting. Love your video and your photos are amazing! I’m adding this to my bucket list 🙂

Angie 23rd September 2016 - 1:12 pm

Despite visiting Chester, I didn’t know the history behind it, or that the clock was the 2nd most photographed so thank you for this information! Your perspective on the buildings is stunning! Once again, although I have been here, your photographic eye gives me a whole new, beautiful way of looking at these gorgeous buildings. You are always so lucky with the weather as well – another gorgeous sunny day with blue skies, I’m jealous! Unfortunately I never made it to the cathedral or castle so may have to return again (we were in Chester to do a shark dive at the aquarium, a Christmas present for one another!). Thank you for showing us again the beauty of England!

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