The small cathedral city that became an unlikely hipster hub

Winchester is a small city stacked with history, as Telegraph readers are no doubt aware. For those in need of a reminder, let me run you through its milestones (deep breath): 

Before the Roman invasion, the place was known as Venta, and it was populated by Gaulish tribes known as the Belgae (insert joke about Britain being forever tied to Brussels here). Its Roman name was Venta Belgarum (see what they did there?); it later became capital of the Anglo-Saxon kingdom of Wessex, and its name morphed into Wintan-Caestre (“caestre” is a mangling of the Latin castrum, fort).

Alfred the Great kicked off some much-needed redevelopment in the ninth century, in order to better fend off marauding Vikings; William the Conqueror, Edward I and others all added to the castle. Though the famous Round Table displayed there has nothing much to do with King Arthur – it dates from the 13th century, and was given an Arthurian makeover by the order of Henry VIII.

In the 14th century the bishop and statesman William of Wykeham founded a college for religious kids, which today claims to be the oldest school in continuous use in the country. Fast forward 500 years. Jane Austen spent her last days here, suffering from a mysterious illness. Then, in the Seventies, Charlie Swan – my old man – met his first girlfriend in the very same house in which the author died. 

Which is why I’ve brought him along. Having spent four years of his schooling here in the early Seventies, I thought he’d make the perfect tour guide. 

We arrive by train from Londinium, and are immediately greeted by metropolitan-hipster home comforts. Trendy cafés (Hoxton Bakehouse has “Hoxton quality” coffee at “Hoxton prices”, according to Dad), barbers (we counted about 10 within a five-minute walk – why so many, Winchester?) and barber-café hybrids are everywhere. 

We head straight to the college, passing by the old cinema where Dad dodged protesting religious types to see The Exorcist, and past Austen’s house. The school is in the nicest part of town – narrow streets and tiny old houses. I recommend popping into cute bookshop P&G Wells; the school itself is worth a tour even if you have no personal connection, as there are some impressive chapels and glass windows to peruse. 

Lunch is at The Wykeham Arms, opposite the school (“we’d get caught here, so we went to The Royal Oak”). It picked up Town Pub of the Year 2018 in The Good Pub Guide, and it’s easy to see why: cosy, well decorated (the tables are old school desks), stocked with local ales and recommended by the likes of Michelin and Harden’s and bearing rosettes, it’s the ideal spot to grab a bite in a town full of high-end chains (your Brasserie Blancs and Ivys, Rick Steins and Loch Fynes).

Winchester’s Christmas market is reckoned to be one of the best in the country and has even been awarded “gold” status, whatever that means. Rows of little Teutonic wooden huts offer bratwurst and mead (of course), and an ice rink for the kids. It’s an ideal place for slightly overpriced festive gifts – think tweed hats and pastel pashminas. There’ll probably be an oompah band playing somewhere, too. Christmas lights here and across town make Winchester a prime destination across the festive period.

As Dad points out, Winchester has changed a lot since the early Seventies. Apart from grandiose religious buildings, the only thing he seems to recognise are the pubs, though perhaps that says more about the priorities of a teenage scholar than the town itself.

Five fine reasons to head to Winchester

The cathedral

An imposing gothic structure where many famous figures are buried, including Jane Austen and William of Wykeham. £8.50 entry.

The mill

Winchester City Mill, on the River Itchen, claims to be the oldest working water mill in the country. Learn to tell your bran from your endosperm, and much more about wheat (plus a couscous reference for the 21st century). £4 entry. 

The cafe

Saint George Tea Room is opposite the Wykeham Arms, and is the ideal spot to stop for a mid-morning pick-me-up. Its interior is cosy leather and wood, there’s a tempting back garden for the summer, and it’s attached to a deli selling some fine produce. 

The pub

“It’s really only the pubs that remain,” says Dad. The Royal Oak, parts of which date back to 1002, is apparently the oldest bar in the country (a lot around here is the oldest this or that), and evidently housed many Seventies schoolkids. But the Wykeham Arms is nicer. 

The museum

Winchester City Museum is a stone’s throw from the cathedral. Its three floors cover the breadth of the city’s history, including Roman-era Venta Belgarum. Free (£3 donation suggested).