No Plan, No Hotel, No Idea…Then Festivals, Parades and Chester City Walls!
- The Best Life Awaits
- Mar 21
- 5 min read
Updated: Mar 24
So you rent a car in Scotland and start driving through the Highlands. You’ve done left-side driving before—just not recently. After a few days, you’re feeling pretty confident as you leave Glasgow.
Then it gets dark. And you don’t have a place to stay.
Yeah… this is kind of how we travel.
We checked the GPS and saw we were near Manchester. As a massive Black Sabbath fan, my first thought was: Ozzy’s hometown! How great would it be to stay there? Then reality kicked in. It was dark, it had been a long day of driving on the wrong side of the road, and I’m not 25 anymore. Maybe… not tonight.
We scanned the map for something smaller and easier to navigate. Not too far away was a place called Chester. Never heard of it. Looked small. Perfect place to spend the night and quietly slip out in the morning. But small towns operate on different rules.
We booked a B&B a few hours earlier and headed over, thinking we’d just grab the key and crash. So my wife and daughter went to check in while I idled in a no-parking zone. Turns out, you can’t check in after 9 PM. We found that out… at midnight.
Has our "play it by ear" strategy finally come back to haunt us? The kids were completely done. They are not fans of our spontaneous wing-it strategy, and at that moment, they were letting us know it.
We checked a large hotel that technically had a room—but it had no windows, no fan, and no air conditioning. It felt less like a hotel room and more like a storage closet with a few cots. They also had about 1,000 wedding goers having their reception! It was noisy for sure. Desperate, we called a number they gave us for a place that wasn't listed online.
Miraculously, The ABode had availability. Not cheap, and we had to book two rooms with single beds, but at that point... It felt like a five-star upgrade from sleeping in a medieval dungeon. Five minutes later, we were checked in and asleep like nothing had ever happened.
The next morning is where everything changed.
What we thought was just a quick, quiet stop turned out to be quite the surprise. Chester isn’t just a small town—it’s a historic walled city. In fact, the Chester City Walls are the most complete city walls in Britain. And you can walk the entire 2-mile (3.2 km) perimeter along the Chester City Walls! So, naturally, we decided to walk it and film the whole thing. I mean, we literally filmed the entire wall.
Okay… 99.9% of it. Our camera battery actually died about 50 feet from where we started, but you get the idea! The views were incredible. Parts of the walls date back nearly 2,000 years to Roman times, when Chester was known as Deva Victrix. Watch our video to see the walk for yourself! Checking into Chester a bit when we got back to the States, it turns out that Chester is often rated as one of Englands prettiest cities. Who know a random stopover could be so special?
We started at the Chester Cathedral and backtrack a bit towards the east clock gate. We then walked the entire wall counterclockwise until we got back to the east gate. We later learned that the Eastgate Clock is one of the most photographed landmarks in England—second only to Big Ben. Our little last minute town is turning out to be quite the tourist destination.
Along the walk, there is plenty to see, including:
Eastgate Clock
Chester Cathedral
River Dee
King Charles Tower
Roman Amphitheatre
Chester Castle
Check this website for more details.
As we reached the southwest corner near Chester Castle, we noticed people weren’t
just walking around—they were dressed like they’d stepped out of the 17th century. We had unknowingly walked straight into the last day of a two day Georgian festival! The festival brought the Georgian era to life — a time when Britain was rapidly changing, growing, and modernizing. Chester Castle actually dates back to the 11th century! It was built shortly after the Norman Conquest. It’s still used today for courts and official functions, not just tourism. That means it's been in use for nearly 1,000 years!
It was great little surprise on our unexpected stop, on an unexpected city wall in Chester. We talked to several re-enactors and explored the castle a bit then headed back to our trek on the wall. We passed by the River Dee and the Old Dee Bridge. A bit further on and heading back on the final leg towards were we started; we came upon old Roman ruins! Turns out, this “small town” was once a major Roman stronghold —with the largest amphitheatre in Britain. This wall (and city) were full of surprises!
If you would love to see everything we did this day, check out the full raw footage video of the Chester City Walls above. And if you are in western England we highly recommend making a stop in Chester!
And then, just when we thought this 'sleepy little town' couldn’t get any livelier… we started hearing drums. We reached the Eastgate Clock and headed down to the center of town.
The streets filled up, and a parade began right in front of us. Out of all the weekends to randomly end up in Chester, we had arrived during the annual Midsummer Watch Parade. We came to Chester by accident, tried to leave as quickly as possible, and somehow ended up walking a historic Roman wall, exploring a Georgian festival, and landing in the middle of a once-a-year parade. What we had no idea about is that this parade dates back to medieval times. Complete with giants, dragons, and characters that have been part of the tradition for centuries.
We came for a place to sleep—but somehow ended up walking through Roman history, medieval traditions, and centuries-old celebrations… all in a single day.
This is exactly why we wing it when we travel.
Because sometimes, the places you never planned to visit end up being the ones you remember most.
Quick Facts About Chester
The Chester City Walls are the most complete in Britain—and you can walk the entire 2-mile loop
Parts of the city date back nearly 2,000 years to Roman times
The Eastgate Clock is the second most photographed clock in England
The Roman Amphitheatre Chester is the largest in Britain
Chester Castle has been in use for nearly 1,000 years
The Chester Midsummer Watch Parade dates back to medieval times
Check our Traveling section for that and other videos from our travels!
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