Our Lives Take Various Paths: Why Winchester is So Special to Me
Our lives take various different paths over the years.
Some people call them “sliding doors” moments—those occasions when you turn left instead of right, make a different decision, or simply decide to do something you wouldn’t normally do. Looking back, you realise that one small decision can change the course of your life forever.
For me, one of those moments happened in Winchester.
At the time, I was living with my parents between Winchester and Eastleigh, having previously lived in Swanmore.
My mates and I would traditionally head off to Southampton for our Friday night entertainment—The Top Rank was the place to be. We’d head there looking for a good night out, great music, and, if we were lucky, perhaps a girlfriend or two.
But on this particular rainy night, for whatever reason, we decided to do something different. We went to Winchester instead.
As luck would have it, I met my first wife. She would go on to become the mother of my children, so that seemingly insignificant decision turned out to be monumental.
And there is another little twist, my brother is still happily married to my first wife’s sister. They met at my wedding rehearsal. You really couldn’t make it up!
So perhaps you can understand why Winchester has always held such a special place in my life.
It’s Not Just About the Memories
My connection with Winchester didn’t end with that chapter. Over the years, I’ve spent many a happy evening making my way around what is famously known as the “Winchester Mile”—that wonderful collection of pubs stretching through the city.
And when I say many a year, I mean it. I suspect I’ve done a reasonably thorough piece of research… purely in the interests of journalism, obviously.
That is the magic of Winchester. It is one of those rare places that manages to be deeply historic without feeling like a static museum piece. It’s a proper, living city—compact, beautifully paved, full of independent shops, fantastic local bakeries, and quiet pub courtyards where you can actually hear yourself talk.
And perhaps that’s why I keep coming back.
The Simple Pleasures of a Winchester Weekend
For us, the real charm of a Winchester weekend isn’t about trying to see everything. It’s the simple things.
Take the River Itchen: you can follow the riverside walk past the water meadows towards St Cross and, within minutes of leaving the High Street, find yourself surrounded by quiet Hampshire countryside. It’s flat, peaceful, and a world away from the noise of everyday life.
After a decent walk, there’s always the important question of food. Winchester has a brilliant food scene—from grabbing a black coffee and a fresh pastry near the Cathedral Close to finding a cosy corner in an old timber-framed pub for a proper long lunch.
The pace forces you to slow down. You don’t need to rush around ticking off a tourist checklist. You wander, browse, stop for lunch, enjoy a coffee, or discover a quiet pub you’ve never noticed before. Somehow, the afternoon just stretches out effortlessly.
And Then There Are the Pubs…
I couldn’t write about Winchester without mentioning the pubs.
While I’ve spent plenty of time working my way around that famous mile, my approach these days is somewhat more selective—age does that to you!
There is one particular spot visitors should seek out: the tiny pub tucked away opposite the cathedral. If you’ve been there, you’ll know exactly which one I mean. If you haven’t, I won’t spoil it; part of the fun of Winchester is discovering these little places for yourself.
Why Winchester Makes Such a Great Weekend Break
Winchester works so well because you don’t need three days packed with activities, nor do you need a rigid plan. You can simply be there.
Have a wander, find somewhere great for lunch, visit the cathedral, walk along the river, explore the independent shops, and enjoy dinner somewhere decent. If you’re feeling adventurous, you can see how many historic pubs you can fit into an evening—though these days, my knees and liver prefer a gentler pace.
That’s the beauty of returning to somewhere you’ve known for decades: you see it differently as you get older. The city hasn’t necessarily changed that much—you have. What once meant late nights and loud music now means good food, a comfortable hotel, a decent walk, a fine glass of wine, and enjoying the atmosphere.
Perhaps that’s one of the great things about life after 60. We don’t always need somewhere brand new. Sometimes, we just need to look at somewhere familiar with fresh eyes.
For me, Winchester isn’t simply an historic city. It’s part of my story. One Friday night, many years ago, a group of us decided to turn left instead of right—and my life changed.
So forget the Round Table for a moment. This is my Winchester.
What about you?
Perhaps that’s what I like most about looking back at Winchester.
It’s not really about the cathedral, the Round Table, the pubs or even the nightlife.
It’s about what happened there.
One Friday night, my mates and I decided to do something different. We turned left instead of right, went to Winchester instead of Southampton, and I met the woman who would become my first wife and the mother of my children.
And from that one decision came a whole series of events that shaped my life.
That’s the funny thing about life.
We rarely know at the time that we’re standing in front of a sliding door.
We simply make a decision.
Sometimes it turns out to be insignificant.
And sometimes, years later, we look back and realise:
That changed everything.
So I’m curious.
What’s your Winchester?
What’s the town or city that has a special place in your life?
Where was your own sliding doors moment — the place where you turned left instead of right and, perhaps without knowing it at the time, changed the direction of your life?
I’d love to hear your story.
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