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All hail Regency Cheltenham!

The insider’s guide to all things quirky and hip, scoffable and quaffable, cultured and kid-friendly, luxe and edgy in the Cotswolds' salubrious spa town.

municipal offices Union Jack flag

Ah, Cheltenham, what a spiffing place, and yes, while there is plenty of Regency loveliness to enjoy and lots of oohing and aahing at gorgeous architecture, it’s not blanket la-di-da in the spa town – honestly, there’s hip and quirky too if you know where to go, which I do natch. So come along and check out my insider’s guide to the super sumptuous and sometimes a bit edgy centre of the Cotswolds.



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The art deco grande dame that is The Daffodil

While any meal at The Ivy Montpellier Brasserie is a delight, breakfast will certainly put a spring in your step for the day ahead. Try and nab a table next to the circular bar that sits under the heavenly dome fashioned after the Pantheon, from where you can eye up a bar stool for later. For something a bit more laid-back, The Scandinavian Coffee Pod tucked away behind the Promenade is where in-the-know coffee lovers go for a caffeine and cool Scandi design fix. And if you’re in the Bath Road / Suffolks ‘hood (Cheltenham’s equivalent to Notting Hill), Brew & Bake specialises in locally produced artisan food and drink with cool, upcycled interiors.

The healthiest place to have lunch has to be Vinnie’s Eatery near the Promenade, which serves up California-style plant-based whole food that is both virtuous and delish. Die-hard carnivores should head to The Fire Station in hip St James Square where slabs of succulent meat are cooked over an open flame on a super-duper Robata grill fired by English oak. Back in the Suffolks, my tip is The Retreat, an old-school wine bar which serves tasty, well-priced brasserie fare by day and transforms into a tempting louche drinking hole by night.

Pretty much next door is The Daffodil, a splendiferous supper spot in the former site of a 1920s cinema. It still retains an air of inter-war Hollywood glamour with its sweeping staircases and art deco flourishes, and the classic menu is top-notch. Come festival time it’s also a venue for live jazz which further boosts its Great Gatsby-esque atmosphere. Foodies will want to head to the nearby Le Champignon Sauvage for its superlative two Michelin-star French fare which it’s been serving up in an understated environment for more than 30 years, while relative newcomer Montpellier Lodge, housed in the former park-keeper’s house in the beautiful Montpellier Gardens, offers high-end, locavore cuisine in the prettiest setting.



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Slick interiors at Malmaison

Cheltenham’s long-standing grande dame The Queens has a lot of young-blooded competition these days, not least from the funky and fabulous Malmaison, which blends its Victorian villa roots with a slick, modernist new build. Also in fancy pants Montpellier is No 131, a Georgian townhouse hotel that likes to party – the restaurant and Crazy Eights bar always draw a lively tribe. For a more homely atmosphere, book yourself into Cheltenham Lawn Guesthouse in Pittville owned by artist Anthea Millier who’s imbued her Regency townhouse with Bloomsbury-style bohemian touches. Couples looking for a romantic pied-à-terre should check out StayCotswold’s The Coach House at Bafford which is luxe self-catering at its best.



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Single tree at the top of Cleeve Hill

There are some beautiful gardens to perambulate in – Montpellier, Imperial and Pittville Park. All three served 18th– and 19th-century health tourists who came to take the waters and you can still taste it at the Town Hall and the majestic Pump Room in Pittville Park (warning: it tastes foul, so be prepared to spit!). If you’ve brought your walking boots, the town is surrounded by glorious hills to trample up – Cleeve and Leckhampton offer appetite-boosting rambles with great vistas to boot. On a clear day you can see the looming Malverns and Black Mountains, and from the top of Cleeve you get an excellent view of the racecourse.



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The atmospheric John Gordons which offers multiple drinking options

There’s no shortage of drinking dens to dive into – AquaVitae, a Champagne and cocktail bar in the centre of town has a good-time reputation and if you’re after an all-nighter it’s an easy stagger down the stairs to its sister 21 Club where you can dance till dawn. Bar 50 in the Suffolks has cool, New York loft-style interiors and lots going on from cocktail-making parties to poker nights, while The Beehive nearby is a bit of a hidden gem with its country pub vibe and atmospheric upstairs dining space. Also big on atmosphere is Montpellier’s John Gordons, a whisky & wine bar, gin & cocktail bar and specialist spirit & wine merchant all rolled into one. The covered courtyard that bridges the two bars is the kind of place that makes you feel like drinking is a creative pursuit à la Hemingway and F Scott Fitzgerald – a great novel must surely come of it.



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Inside the Bodega fashion emporium

Cheltenham is a magnet for shoppers, with the Promenade acting as its de facto King’s Road. Toast, The White Company, Hobbs and Jack Wills all reside there, not to mention Cavendish House, a House of Fraser department store that’s been there since the year dot, and purveyor of handmade Italian footwear Keith Scarrott Shoes. Excitement is mounting as the opening of John Lewis on the High Street draws near, though contractual wrangles means it’s taking forever! Just off the High Street round the corner from M&S is the brilliant indie fashion boutique Olive which sells cool, Cos-style designs for men and women. Funky menswear shop The Union Project, which has just moved from Montpellier into bigger premises off the High Street, stocks hard-to-find labels such as Stüssy, Carharrt WIP and Sunspel. The Suffolks and Montpellier is rich in indie shops too. The snazzy fashion boutique Bodega has niche labels and staff with an eye to what suits. Lots of leopard skin too, yum. For interiors, Skandic Hus is your go-to for slick Scandinavian design, and if you’re looking for one-off, handmade designs, The Guild at 51 serves as shop-cum-gallery for the work of the Gloucestershire Guild of Craftsmen, who are a very talented bunch judging by the wares on show.



Gustav Holst piano

Gustav Holst’s piano on display at the house where he was born

It’s not a massive town for tourist haunts, but you do have The Wilson art gallery and museum, named after Edward Wilson who died with Scott in the Antarctic, with its collection of decorative arts, costumes and textiles, fine art and suchlike, and the Holst Birthplace Museum, which does what it says on the tin and passes a pleasant couple of hours. Brian Jones was also born in Cheltenham (he went to school with my dad!), but there’s nothing to mark his birthplace which seems an omission to me. He lived on Hatherley Road just before the Parish Church and went to Dean Close School if you want to make a private pilgrimage, and is buried in Cheltenham Cemetery, though again, no Jim Morrison-style groupies, which is probably a good thing.



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Cheltenham’s open-air lido is glorious – and the water is heated!

If it’s not freezing, Sandford Parks Lido is a gorgeous, 1930s open-air, HEATED pool that’s massive and has a substantial kiddies’ pool for babies and toddlers too. It’s a great space with beautiful lawns to stretch out and picnic on, and it’s literally five minutes’ from the centre. Another water-based distraction is rowing in Pittville Park, which has boats for up to five people and pretty parkland to admire. Indoor entertainment doesn’t get much better than Hollywood Bowl in the Brewery Quarter which, as well as bowling, has pool tables, slot machines and air hockey games to keep all ages amused. The Brewery is also the place to come for all manner of kid-friendly restaurants chains, from Five Guys to Nando’s. But if you want the best burger in Cheltenham, head to Real Burger off the High Street. And for pizza Fat Toni’s behind the Promenade is epic.



Regency House Cheltenham

Suitably creepy shot of the house in Pittville that the Woman in Black is said to haunt

Apparently, there are quite a few ghosts in the area – one supposedly haunts the Everyman Theatre and there have been numerous sightings at a house in Pittville of the ‘Woman in Black’ who inspired Susan Hill’s novel of the same name. Prestbury on the outskirts of town is supposedly the most haunted village in England with the infamous Black Abbot who paces the churchyard, the Headless Horseman, who, legend has it, was a royal dispatch rider beheaded by the village Roundheads, and the Medieval Messenger, not to mention a pub which has no less than nine ghosts. Cotswolds Ghost Tours can show you round if paranormal activity is your bag.



horses racing with jockeys

The famous Cheltenham Jockey Club always gets bums on seats

Where to start? Cheltenham is the town of festivals – literature, its most famous, in October (Hillary Clinton headlined last year), jazz in May, science in June and music in July. There’s also the gee-gees of course, which during Gold Cup week in March sees the town flooded with tweed-clad revellers. And the Food & Drink Festival in June is no small beer either (this year Oz Clarke is coming for master wine classes, hiccup). If art is your thing, head to the always stimulating Chapel Arts gallery (nice café too), while the Victorian Grade II-listed Everyman Theatre puts on a consistently vibrant programme of drama, opera, ballet, comedy and panto.



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The moody mezzanine lounge bar at The Clarence Social

The Coconut Tree in edgy St Paul’s is the place to be according to personages younger than me. A bar-cum-eatery founded by a group of London exiles, it serves up taste bud-titillating Sri Lankan street food, candles in coconuts and sweet and fiery Cocotails that’ll put a swing in your step when the volume gets pumped up. Back in town, The Clarence Social  has a London members’ club vibe with a ground floor coffee venue that turns into a buzzy bar by night, a mezzanine lounge bar that Don Draper wouldn’t look out of place in and a nostalgic basement speakeasy.



Check out the brand new Insider Guides to cities and towns from the other Muddy Stilettos editors…


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