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The Insider Guide to Winchester

From Austen and Keats to quirky street theatre and gin: where to scoff, quaff, shop, nose and snooze in King Alfred's capital.

History at every corner, fabulous places to eat drink and shop and dreamy Hampshire countryside in all directions. Wonderful Winchester is one the coolest Cathedral cities in the country. And it’s an absolutely brilliant place to go to for a weekend break – whatever the season.

An ex-resident, it’s no accident I still live within striking distance down the A272. And I’ll happily pop back whenever a decent excuse presents itself. Park that dodgy old Winchester guide book and come with me…


Inn the Park new restaurant cafe wine bar Winchester

The city is full of splendid old pubs and independent eateries. Then there’s the brilliant bistros like The Ivy and celeb-chef restaurant outposts like Rick Stein Winchester and Brasserie Blanc.

For special occasion-style fine-dining you can’t go wrong with the Michelin-rated Black Rat and The Chesil Rectory .

Opened in 2021 and (whisper it) quite a lot cooler than it’s older sibling, Inn the Park from the Chesil team (above) is already one of the hottest tables in town. International palate? Try Palm Pan Asia for Thai and (you guessed it) Pan Asian cuisine or Michelin-rated Kyoto Kitchen with its beautifully crafted Japanese food and Hants-grown wasabi.

For proper pub grub, head for one of The Little Pub Group’s eateries like St James Tavern (pies, burgers and curries all the way), The Green Man or The Corner House. Elsewhere, The Black Boy (cosy sister pub to the The Black Rat) is traditional to the core with local ales, good French wine: dogs fine, children on leads, please. If it is family friendly you’re after, it’s a short hop to The White Horse in nearby Otterbourne with it’s outdoor terrace, play area and something-for-everyone menu.

Finally, you couldn’t do a Winch-pub round-up without mentioning Rick Stein favourite, The Wyckham Arms. It’s sandwiched between the Cathedral and Winchester College in the city’s best-kept secret: Kingsgate village.

If the sun has his sombrero on, the Bishop on the Bridge beer garden overlooking the river is always my go to. Or head to the farmer’s market, grab some Hampshire nibbles and spread a blanket on the grassy area in front of the Cathedral. The Farmer’s Market pops-up on the High St every second and final Sunday of the month; it’s the UK’s largest and, according to The Guardian, also the best.


Rawberry cafe Winchester

Rawberry for brilliantly tasty veggie/vegan/healthy juices, bagels and salads; Coffee Lab just off the High Street on St Thomas St for its open, airy community vibe and Josie’s at the top of town on Jewry St for brunch. Also on St. Thomas St, pretty pink Insta-worthy interiors, cakes (and coffees!) are trending at newcomer Ashby’s.

Hoxton Bakehouse on Jewry St is heaven for any self-respecting sourdough-obsessive – expect decent coffee and to-die-for buns. And much excitement too for the imminent launch of The Winchester Bakery, a smart new High Street cafe and takeaway headed-up by ex-Bertinet baker Darren North.


Hotel Du Vin Garden

In the city centre, it’s got to be the first Hotel du Vin (above). Housed in a beautiful Georgian building in the heart of town, expect pampery rooms, a buzzy bar, and great food. (Fun fact: James Martin was head chef here many moons ago before TV came calling).

The Winchester Hotel & Spa also has a smart, boutique feel and a great central location. Even better, it’s just putting the finishing touches to a shiny new spa refurb, due for completion by Summer 2022 (robe and slippers at the ready, ladies).

Elsewhere, The Black Hole B&B (affiliated with The Black Rat) has a more tongue-in-cheek, prison-chic vibe. Or, if you’re after a cosy pub with rooms, try The King Alfred.

Just under four miles out of the city, the 5-star Lainston House is a fabulously luxe hotel in a grand 17th-century mansion. Make time to explore if you do plump for this one. There’s 63 acres of parkland, a cookery school, fine-dining, afternoon tea/champs on the lawn, a new wood-fired kitchen restaurant, kitchen garden and beautiful resident barn owl.


Winchester Cathedral

Calling all history geeks and literature lovers, this one’s for you. Cross the close, pass the city’s 11th-century Cathedral. Gawp, marvel, take the obligatory selfie/stories update. Then head west into Kingsgate village with its tangle of Georgian and Tudor architecture surrounding Hogwarts, sorry, err, Winchester College.

Spot the Wykehamists channeling Harry Potter in their coats and tails; stop for a browse at the wonderful, 250-year-old P&G Wells Booksellers. Onwards along College Street past the house where Jane Austen died, now a private residence. Then follow the River Itchen into the countryside and the water meadows where Keats riffed on “mists and mellow fruitfulness” in Ode to Autumn. 

Pass the medieval Almshouse, then expect a serious climb up St Catherine’s Hill which opens onto the sweeping South Downs stretching all the way to Brighton — well howdy there Muddy Sussex *waves*. If you need a pitstop, the sustainable, community bikestop Handlebar Cafe in a disused railway embankment is well worth a look.


Incgonito winchester best bar
Incognito, Winchester

It may have been a religious centre for fifteen centuries, but the city doesn’t half like a drink. It’s crammed with proper, old-school boozers: see the ‘eat’ section. Newly refurbed, The William Walker by the Cathedral Close also deserves a mention for pure history (William Walker was a deep sea diver who took a quick dip in the Cathedral’s flooded foundations thus saving this incredible building) and The Mucky Duck in Hyde for its community vibe.

For cocktail lovers, there’s Jewry Street’s The Cabinet Rooms, a café-bar with an eye-watering range of gins, many local, like Twisted Nose. For craft ale head to Overdraft also on Jewry St, with its Mexican street-food, DJ’s and Millennial crowd. Or try The Black Bottle for a decidedly grown-up version of your standard bubble-gum machine: 32 wines dispensed by the glass. Finally, there’s the Muddy Award-winning gin parlour (and home of curious smoking cocktails), Incognito (pictured).

If you want to buy a bottle, try boutique merchant Wine Utopia on St Thomas St. For Italophiles there’s Toscanaccio, another Parchment St stalwart whose deli also stocks edible Italian goodies. Check the website for a lively calendar of tastings, tipsy book club and games.


H&B Style Winchester shop interior

Winchester has some special indy boutiques, mostly hidden off the High St. Explore Kingsgate Village and find vintage finds at Stardust Years. On Thomas Street, Muddy loves the brilliant H&B Style (above) for boutique fashion finds and quirky/cool gifts – including stylish, bloke-friendly gadgets.

Elsewhere, serial Muddy Award Winner Sass & Edge on Southgate St do chic and easy womenswear. And try perennial favourite, The Hambledon in The Square for gifts, accessories and fashion.


Winchester Cathedral

First and foremost, the Cathedral. It’s worth paying the entrance price and going inside to really get a sense if this incredible, expansive space. Plump for a crypt tour to see brilliant Brit sculptor Antony Gormley’s mysterious man, tucked away and amazingly atmospheric in the eerie stillness. (No self-respecting Winchester guide would be complete without a mention).

Look up, look down and all around – don’t mind the locals, they’re used to it, but do try not to bump into one. There’s history at every turn and you’re walking in the shadows of Romans, the great Saxon King Alfred the Great (quite literally, if you snap a selfie with his statue at the bottom end of town).

Myth or real man – the jury’s out on whether he actually existed but the legendary Celtic King Arthur is also thought to have ruled here too. Spoiler alert, the grand Arthurian Round Table in the Great Hall doesn’t go that far back but it does date back to around 1290 – and, along with the dour-looking Queen Victoria statue and pretty garden, it’s well worth a look.

Winchester City Museum is tucked just off the High St and worth a browse for the 3D model of the city alone – it took nine years to make. And if you fancy nosing around the UK’s oldest public school, Winchester College, you can book yourself on a tour.

There’s also a slew of military museums if that’s your thing. Or jump on a bus with Grape and Grain tours to discover Hampshire’s burgeoning wine and gin scene. Irrepressible spirits expert and Winchester producers guide, Joel, will pick you up in the city and zoom you round the county’s best vineyards and spirit producers including Hattingley Valley Wines, Winchester Distillery and Red Cat Brewing.


Lots of simple pleasures for toddlers: the grassy area by the Cathedral is wonderful for picnics and run-arounds, there’s also a play-park at the bottom of town near the King Alfred Statue (and, happily, right next to Inn the Park in the Abbey Mill Gardens).

For older kids, try the National Trust’s City Mill, also at the bottom of town — have a go at grinding corn and challenge them to spot an otter. Winchester City Museum is also worth a gander, there are floors on the city’s Roman and Anglo Saxon past plus the building is on the spot of William the Conqueror’s palace so lots of opportunities to link-up with school history lessons.

A run up St Catherine’s Hill is always fun and there are normally make-shift rope swings at the top, plus glorious views of the Cathedral for us olds. Make an afternoon of it at the Winchester Science Centre and Planetarium (pictured above). It’s a ten minute drive outside the city and brilliant for children aged around 5 – 12.


It’s got to be the the Hat Fair (named after the busker’s money-collecting hat). Held over the first weekend in July, the city’s annual circus festival pops-up with colour, joy and giggles. We’re also big fans of the National Trust City Mill’s annual Grand Duck Race (the yellow bath kind), launched each summer into the River Itchen.


Hendog street art Winchester boy building blocks

The city has an incredibly rich calendar of festivals and events from the Cabinet Room’s Ginchester Fête to Winchester Fashion Week. Music-wise, there’s CarFest and the Boomtown festival.

Recently rebranded as the Arc and visited by HRH Prince Charles, the Winchester Discovery Centre (err, basically the library) is the city’s cultural hub. Natural light pours into the atrium, there’s a café, an upstairs exhibition space, a workshop space and a bigger auditorium.

Next door is the more traditional Theatre Royal, with lots of comedy, quirky panto dames (above). Plus children’s theatre, dance and touring plays. If film’s your thing, the city’s Everyman cinema shows a decent selection of indie offerings. Plus live-streaming ballet, opera and NT plays. If this all feels too polished and perfect, head to The Railway Inn for gutsy blues, club-nights, poetry and more.

Banksy fan? Hampshire’s answer to the street art king is our very own Hendog. Find his kite-flying girl at St. Catherine’s Hill and his tribute to our indie business heroes, a child constructing a wall of multi-coloured building blocks (above), on St. Thomas Street.

Fancy a stay-cay or weekender slightly further afield? Check out our bang-up-to-date insider guides to these top towns and cities across the Muddy counties.

1 comment on “The Insider Guide to Winchester”

  • penny November 30, 2018

    An amazing amount of information – I will visit soon !PHK


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