Ian and Nicky New Zealand

24 July 2021

By Ian Mackenzie


Dating back to the Roman period, the medieval city of Chester is comparable to Bath, York and Lincoln - here's how to explore it on foot

24 July 2021

By Ian Mackenzie

This post is one of a series of articles featuring some of the places I was familiar with whilst growing up in Cheshire, England. Indeed, the recent lockdown and subsequent international travel restrictions have given me the perfect opportunity to revisit some old haunts – and discover some new ones along the way. And, hopefully, if you’re visiting this corner of northwest England, you might be inclined to try them out, too!

As a kid growing up on the Wirral Peninsula, I always considered it a special treat to be taken out by my two aunts on a day trip to Chester. It usually involved a visit to the zoo followed by a gentle row along the River Dee in a hired boat. All finished off with a fish and chips takeaway before returning back home in time for the latest edition of The High Chaparral. 

Nowadays I’d probably skip the zoo. I still haven’t mastered rowing a boat in a straight line. And the High Chaparral has yet to make it on to Netflix. But Chester, a beautiful walled city originally founded by the Romans, is just as alluring as ever.

And the good news is that its ancient centre can be explored on foot in a day. Or maybe more if you’re into boutique shopping. And especially if you want to check out my recommended pubs, too! 


About Chester

As the famous line from Monty Python’s Life Of Brian goes, “What have the Romans ever done for us”?

Well, they gave us Fortress Deva, for a start. With its commanding city walls constructed from local sandstone and a huge natural harbour, it became one of Britain’s most important Roman settlements. Later, the Vikings sailed up the River Dee to engage in their favourite pastime of looting and pillaging. But it was the Normans who left their indelible mark on the city, eventually conquering what was England’s last remaining bastion after the Battle of Hastings in 1066.

Now renamed “Chester”, William the Conqueror inaugurated the First Earl Of Chester to watch over the city. It continued to flourish well into the Middle Ages when some of the black-and-white half-timbered buildings that stand today were built. Including the iconic “Rows” – two-tiered medieval galleries above street level.

Unfortunately for the city, the once-proud harbour gradually silted up over the centuries, until the port itself was effectively lost. Instead, Chester – as the county town (or “capital”) of Cheshire – became a haven for wealthy merchants and their elegant houses.

Nowadays, it’s well and truly on the tourist trail for those international visitors who manage to venture away from London. Although perhaps less famous than its counterparts such as York, Lincoln and Bath, it still manages to attract crowds during the summer months eager to spend money in its boutique shops, medieval pubs and enticing ice cream parlours.

A row of ancient buildings with a sandstone bridge and a clock on top

Eastgate Street and its famous clock

A row of ancient buildings with a sandstone bridge and a clock on top

Eastgate Street and its famous clock

Walking the Chester Walls

When considering how to explore Chester, there are a couple of options to choose from. You’ll definitely want to walk the two-mile circumference of the city walls. From where you can hop on and off to explore the medieval streets along the way. Or, as we prefer, you can do those two things separately. In other words, walk the city walls in their entirety and then explore the medieval centre afterwards. 

You can also start the city walls walk at a number of different places – probably depending on whether you arrive by bus, train or car. But, for the purposes of this article, we’ve started at the Bridgegate, down on the River Dee. From where you can then take an additional walk along its banks.

From the Bridgegate to The Roodee Racecourse

The Bridgegate marks the point where the Old Dee Bridge (built in 1387) crosses the river from Handbridge before entering the city. Below the bridge is one of Chester’s most iconic features – the great weir. Built in 1093 to supply power to the first Earl of Chester’s corn mills, it had a major impact on the silting process on the river. Nowadays it gets more attention from kayakers who congregate around it as part of their city kayaking tour.

A river in the foreground with sandstone buildings, a wall and trees in the background

The weir

Heading in a clockwise direction, the walk then passes Chester Castle. Built beside the Dee by the Normans, it was subsequently used as a base to attack and conquer nearby North Wales. In 1696 it was established as a Mint under the stewardship of one Edmund Halley (of Halley’s Comet fame). Sadly, it’s been allowed to fall into a bad state of disrepair over the decades, so it compares poorly with some of England’s other great castles.

Across Grosvenor Bridge, the route then enters an area known as “The Roodee”. Originally part of the old Roman harbour, the silting up of the river created a grassy meadow which was eventually used as the foundation for the world’s oldest racecourse still in operation. In fact, by taking the steps down to the racecourse, you can actually still see some of the original Roman anchor stones.

Race meetings at The Roodee are one of the biggest events in the city’s calendar. And, if you time your visit right, you can watch the action from your route on the wall for free.

Beyond the racecourse, the wall continues almost directly across the red rooftops of the buildings below before heading towards the Watertower.

A path and a wall runs along  to the left overlooking a racecourse to the right

View of The Roodee Racecourse from the wall path

Red rooftops with chimneys to the left, a wall and footpath to the right

The wall route almost runs across rooftops

To the Northgate and Eastgate

The next point of interest is the magnificently named 10th Century Bonewaldesthorne’s Tower, built as an extension to the city’s walls on the river’s edge to protect the port by the Anglo-Saxon Queen Aethelflaed (granddaughter of Alfred The Great). Its richly coloured sandstone and hexagonal shape make it one of the most instantly recognised of all the towers on the route.

As the river gradually silted up, however, the tower lost some of its effectiveness as ships were no longer able to sail up to it. As a result, during the 14th Century, a new tower was built on the river so that cargo could be unloaded and transported into the city via a causeway and Bonewaldesthorne’s Tower. 

Of course, the Watertower, as it became known, eventually succumbed to the onslaught of silting. But gazing out towards it does allow you to imagine those wooden ships cruising in to dock, their sails billowing mildly in the breeze. And the sound of rum-soaked sailors onboard calling out to their counterparts ashore. Or maybe that’s just my romanticised imagination running wild.

By the way, if you fancy a break at this point, some steps lead down from Bonewaldesthorne’s Tower and across to Tower Wharf, where the excellent Telford’s Warehouse awaits you. Back in the 18th Century, it was a canal-side warehouse, but today it’s a lovingly restored pub and music venue with outside seating beside the canal. Recommended!

Beyond the tower, the wall route then heads upwards towards its highest point at the Northgate. Site of a notorious gaol (or “jail”) for over 700 years, the gate was completely rebuilt in the 18th Century. 

The North Wall path then narrows as it passes between the Shropshire Union Canal on the left and boutique studio buildings to the right, before arriving at the Phoenix Tower (aka “The King Charles’s Tower”). Originally a medieval lookout, it became a meeting place for some of Chester’s guilds (or craftsmen). But it was given its second name after King Charles I reputedly stood there to watch his forces lose to Oliver Cromwell’s army in the Battle of Rowton Moor in 1645 (during the English Civil War).

And then it’s onwards, past the impressive Chester Cathedral, until you reach the Eastgate with its iconic clock. Probably the most photographed spot in Chester – and the second-most photographed clock in Britain (behind Big Ben) – it was unveiled in 1899 to commemorate Queen Victoria’s Diamond Jubilee (60 years on the throne). Which becomes immediately clear once you spot the royal crowns and gilded initials, “VR”, on all four sides.

A sandstone tower stands amongst trees

Bonewaldesthorne’s Tower

Stone steps lead up to a wooden door on a tower

The Phoenix Tower (AKA King Charles Tower)

A bridge is topped with a clocktower

The Eastgate clock

To the River Dee

From Eastgate, the route gets a little ugly for a while – unfortunately, a tribute to some of the brutalist architecture of the 60s and 70s that’s blighted parts of the city. They even bulldozed an ancient Roman bathhouse for goodness sake.

All of which becomes a  stark reality when you arrive at the next ancient entrance to the city. Wolfgate (or “Peppergate”) was the original entrance. But its narrowness meant that, come the age of the motor car, it was no longer viable as a thoroughfare. So, in 1938 the larger Newgate was built as a replacement. All very classic Chester sandstone. Until you spot the monstrous multi-storey car park directly behind it!

From the top of the gate, you can see the partially excavated remains of the largest stone-built Roman amphitheatre in Britain. In truth, it’s not much to look at, so your imagination might have to do the rest. But it’s an important historical site nonetheless.

On the other side of the gate, the “Roman Garden” is an attempt to recover some of the city’s other lost Roman treasures. It’s actually just a random collection of ancient stones excavated from across the city to be kept in one place, along with mosaics and landscaped gardens.

Adjacent to it, to the right of the wall, there’s a row of former 17th-Century almshouses to admire. Known as “The Nine Houses”, the qualification for residency included being over 65 years old and a commitment to abstain from tobacco and alcohol. Just six of them remain today but they’re among the best-preserved buildings in the city.

After which, the wall winds its way down to where it meets the River Dee once more at the Bridgegate.

A stone bridge crosses a busy road

Classic Chester (Newgate) vs 1970s-era monstrosities (the car park)

A circular mosaic in the foreground and a park with ancient stones in the background

Entrance to the Roman Garden

A brick building with black and white half-timbered facade on the first floor

Two of the “nine houses”

Walking beside the River Dee

The Groves

An 18th Century promenade called “The Groves” runs alongside the river and has been a magnet for weekend visitors for decades. Drawn to its combination of watery pastimes – rowing boats, motorboats and pleasure cruises upriver – with scenic walks, local ice cream and a riverside pub, it’s a taste of traditional Chester that hasn’t changed much over the course of time. There’s even an Edwardian bandstand that’s featured performances since 1913.

By the way, both the Snugburys and Cheshire Farm outlets serve excellent ice creams.

Following the promenade, all the way to The Boathouse (with its floating beer garden and beach huts), a pathway leads into the 20-acre Grosvenor Park – one of the finest Victorian public parks in the country.

Then, by doubling back through the park you’ll eventually arrive at the Queens Park Suspension Bridge before crossing the river.

A red pagoda in the foreground stands next to a river with two boats in the background

The Groves

Two boats moored on a river with a stone bridge in the background

The Groves

The Meadows

By crossing the river via the bridge and then turning left you’ll wander along the opposite bank of the Dee and into an area called “The Meadows”. Which, not surprisingly, features a large meadow that’s usually home to grazing cows. 

The advantage of walking here is that you can take in the views of the rowing clubs, mansions and terraces on the city side of the river. As well as the activity on the river itself. Just take the path for as long as you want before doubling back once more across the bridge and onwards to the Bridgegate.

A field with yellow flowers in the foreground with red brick houses with white pillars in the background

Terraced housing beside the River Dee

A filed of yellow flowers in the foreground and a large red-bricked building with with a spire in the background

Another view from The Meadows across to the opposite bank of the Dee

Exploring the city centre

Bridge Street (Lower & Upper)

Now it’s time to explore the ancient city within the walls, focusing mainly on the four original Roman streets of Bridge, Watergate, Eastgate and Northgate. Featuring a mixture of medieval, Tudor, Victorian and Georgian architecture, some with vaulted crypts and cellars, it’s worth spending some time here. Both in and outside the buildings. 

Once through the Bridgegate, you’ll arrive in Lower Bridge Street, where you’ll get your first proper closeups of Chester’s gorgeous architecture. And, if you happen to make it here around lunchtime you may want to stop off at one of the many enticing pubs on offer. 

The first stop might be the ridiculously beautiful and rambling timbered building that houses the Bear & Billet – generally recognised as Chester’s finest 17th Century timber-framed townhouse.

Better still, in my opinion, the Brewery Tap – just a hundred metres-or-so further along – would be my choice of unmissable Chester pubs. Accessed via a set of steps off the street, once through the entrance, you’ll enter a grand Jacobean hall where a range of beers from the local Spitting Feathers brewery is ready to sample. And the food’s good, too.

As a matter of interest, when King Charles I trotted into town in 1645 with his entourage of 600 men on horseback, he stayed overnight in Gamul House (as the building was then known) before and after the famous Battle of Rowton Heath. Back then it was the residence of Chester’s Mayor – so an early version of an Airbnb, then.

Finally, I couldn’t leave Lower Bridge Street without mentioning The Falcon, on the crossroads with Grosvenor Street and Pepper Street. Another stunning timber-framed building dating back to the 12th Century, it was a regular haunt of mine back in the day.

A whitewashed building with a black and white half-timbered facade on the first floor

Ye Olde Kings Head, Lower Bridge Street

A red wall hides steps leading up to a door on a red bricked building

The Brewery Tap (previously Gamul House)

Over the crossroads, Upper Bridge Street is fully paved and traffic-free. And the pubs are replaced mainly by shops, cafés and restaurants, which spill out onto the street during the summer months. 

If you’ve arrived following our route it’ll be your first chance to see The Rows – more on them later. But this section of the street does include the ”Three Old Arches” – said to be the oldest existing shop front in England (1274).

By way of contrast, hidden behind The Rows on the opposite side of the street, The Cavern Of The Curious Gnome is a wine bar-cum-pub spread over two floors, the upper of which features toadstools, gnomes and various other quirky pieces of decor. Along with stained glass windows and a huge selection of British, German and Belgian beers.

A cream-coloured building with three archways on the first floor

Historic arches on Bridge Street

The High Cross & Watergate Street

Each of Chester’s original Roman Roads meets at the sandstone High Cross, where public proclamations have been carried out since the 14th Century. It’s from here that Chester’s Town Crier, dressed in a red and gold tunic and feathered tricorne hat, rings his bell and yells out his midday proclamations (beginning with “Oyez, oyez, oyez!”).

Not every day mind you. Tuesday to Saturday during the summer months at noon. Or 11 am on race days. Which tells you it’s as much to do with tourism as it is tradition.

Turning left into Watergate Street, one of the first buildings you’ll encounter is the 17th-Century “God’s Providence House” with its inscription “God’s Providence is mine Inheritance”. The phrase is thought to be a thank you for deliverance from the plague that ravaged the city in 1647-48.

Then there’s the Old Crypt. Although a five-storey building, two of its floors are underground (dating from 1180) and one is within The Rows. And because it’s a pub (Watergate’s Bar), you can take a look inside the vaulted stone crypt itself.

Indeed, the street has plenty of options to eat and drink. My pick would be Ye Olde Custom House, a 17th-Century former Custom & Excise building decked out in Chester’s signature sandstone base and timber-framed first floor.

A sandstone cross on the left stands on a crossroads with black and white half-timbered buildings in the background

Chester Cross on the corner of Bridge Street and Eastgate Street

A sandstone building with a black and white half-timbered facade on the first floor

Ye Olde Custom House, Watergate Street

Eastgate Street

The other side of the Cross leads into Eastgate Street. But, although the black-and-white timbered buildings look particularly well-preserved, they actually feature “Mock-Tudor” facades constructed in the 19th-Century.

Home to the Eastgate clock, the street is also notable for housing two of Chester’s most famous institutions – the opulent Grosvenor Hotel and the sadly-now-departed Browns of Chester department store, which until this year had been open for business since 1791.

Of course, I couldn’t move on without featuring at least one of the street’s historic pubs. This time it’s actually the city’s oldest. Ye Olde Boot Inn has occupied the first floor Row of the building since 1750 and, as you might expect, it’s full of twisted wooden beams and dripping in atmosphere.

A black and white half-timbered building on the left leads to a sandstone bridge with a clock on top

Eastgate Street

St Werburgh Street

Back towards the Cross, St Werburgh Street leads off to the right and onward to Chester Cathedral. Most of it was built in the late 1890s after the demolition of the original housing. But, although the superb black-and-white half-timbered terraced buildings are very much of the Mock-Tudor variety, the street is still worth taking a stroll through it until you reach the cathedral and Northgate Street.

A row of sandstone buildings with black and white half-timbered facades

Corner of Eastgate Street and St Werburgh Street

A sandstone buildings with an archway running between it and the road

St Werburgh Street

Northgate Street

Home to the Chester Cathedral and the Town Hall, Northgate Street is also notable for the two sets of Rows opposite each other.

Shoemakers Row is another Mock-Tudor extravaganza and was named as such because… well, you can probably guess. There’s even a carved figure of St Crispin (the patron saint of shoemakers) watching over proceedings below from a top-storey window.

Opposite, the markedly less-grand Broken Shin Row refers to the “rugged and uneven character of the thoroughfare and the manifest dangers that threatened the shins of those who ventured along it”. It’s also pretty dark so if you’re going to skip any of the Rows, it’s probably best to make it this one.

Disappointingly there aren’t any decent pubs on this street I can recommend. Although the Dublin Packet (on Shoemakers Row) is notable as being where Everton and England footballing legend, William “Dixie” Dean earned a living as a pub landlord after retiring from the game. If you’re not familiar with who Dixie was, he holds the English record for scoring most league goals (60) in one season (1927-28). How times have changed. Somehow, I doubt Ronaldo or Lionel Messi will be pulling pints in a bar near you any time soon.

A black and white half-timbered building with paved archway on the ground floor

Shoemakers Row, Northgate Street

More about The Rows

Unique to Chester, the history of The Rows dates back to the 13th Century, but the reason why they were built is open to speculation. One theory is that the Roman walls restricted the amount of space available to expand the city’s commercial potential. So the townsfolk were forced to build upwards rather than outward.

The most common theory, though, is that the crumbling buildings of the Roman period were simply built upon with some of the classical structures being retained and extended.

Over the decades and centuries, sections of The Rows have been blocked off as new buildings have emerged. Elsewhere new sections have been added to retain the original characteristics. 

During the Middle Ages (13th to 15th Centuries), there were shops at street level, whereas the living quarters were above, in the gallery. By the time of the Tudors and Jacobeans (1485-1625), the upper floors extended out beyond the gallery and were supported down to the street by long poles. It was in-between these poles that shopkeepers displayed their goods.

Nowadays, the premises on both the street and Row levels include not only shops but restaurants, cafés and offices. Many of them have their own special atmosphere retained from a bygone age. But it’s the wonderfully evocative covered walkways overlooking the streets through archways and balustrades that will linger most in your memory.

A passageway runs beneath a row of buildings
View of a black and white half-timbered building through an arch
Am enclosed passageway with railings above the street to the right
View of red-bricked buildings through an arch

Final thoughts

I’ve mentioned that you could conceivably complete the walks in this article over the course of a day. However, if you’d like to take a real deep dive into the history of the buildings I’d recommend you bookmark the links I’ve provided for each of the four main streets and refer to them as you walk around.

The articles provide a fascinating insight into EVERY building on each street. And the antique photographs, paintings and drawings will help you to compare the past with what you’re looking at today. Just allow an extra day or two to get around!

Here are the links again:

Northgate Street

Eastgate Street

Watergate Street

Bridge Street

Chester Walls

Of course, if you need any help in planning your trip to Chester, feel free to reach out and I’ll do my best to help.

A black and white half-timbered facade with four windows and two statues

Shoemakers Row, Northgate Street

A black and white half-timbered facade with four windows and two statues

Shoemakers Row, Northgate Street

What did you think? Have you been to Chester? Or maybe you’re thinking of visiting the village in the near future? Either way, we’d love to hear from you so please add your comments below.

Other posts in this series:

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Dating back to the Roman period, the medieval city of Chester is comparable to Bath, York and Lincoln - here's how to explore it on foot
Ian and Nicky New Zealand

Hi, we’re Ian and Nicky, an English couple on a voyage of discovery around the world, and this blog is designed to reflect what we see, think and do. Actually, we’d like to think it also provides information, entertainment and inspiration for other “mature” travellers, too. So please feel free to pour yourself a glass of something suitably chilled and take a look around.

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