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The insider guide to Cheltenham

Seeking the holy grail of a town that offers majestic heritage with the coolest of cosmopolitan vibes? Put Regency Cheltenham at the top of your list. Read our insider guide to all things quirky and hip, scoffable and quaffable, cultured and kid-friendly, luxe and edgy in the Cotswolds' finest spa town.

The salubrious town of Cheltenham Spa is one spiffing place. It may be best known for its Regency loveliness with grand tree-lined Promenades, pretty parks and swoon-worthy architecture, but this hotspot has a super hip and edgy side too.

From swanky boutiques and artisan makers to a laid-back cosmopolitan feel, this is a countryside-with-benefits kind of place. Not only voted the ‘Best place to live in the South West 2020’ by The Sunday Times but also taking the crown in Muddy Stilettos reader-voted Best Places to Live 2022.

Just over two hours from London and with enough retail and cool bars to keep any ex-urbanite happy, it has an arts, culture and festival calendar to rival the capital.

EAT

The stunning Ivy Montpellier

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 cocktail bar that sits under the heavenly dome fashioned after the Pantheon, from where you can eye up a bar stool for later.

Other gourmet greats are Raymond Blanc’s Brasserie Blanc with its hearty French menu and lovely new outdoor heated terrace, and GL50, for the best relaxed fine-dining in the town, with a menu created by a Michelin-trained chef.

Delicious dishes at Brasserie Blanc

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 or Suffolks hood (Cheltenham’s equivalent to Notting Hill), Brew & Bake specialises in locally produced artisan food and drink, the best cakes and brownies, and cool, upcycled interiors.

For Japanese cuisine head to 2021 Muddy Award winner KIBOU for the best sushi and sashimi, and one of our fave places for a healthy brunch is The Find, who make an awesome Smashed Avocado on Sourdough.

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 1920’s 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.

STAY

Cheltenham’s long-standing grande dame The Queens is a stand-out place to stay. Steeped in history it has the most sumptuous interiors and a stand-out restaurant with Victoria’s too. Also in stylish Montpellier is No 131, a Georgian townhouse hotel that likes to party – the restaurant and Gin & Juice Bar always draw a lively tribe, and there’s a great new alfresco covered terrace too featuring a Japanese restaurant.

The beautiful No.131

Another contender is Malmaison with its colour pops and brooding interiors, plus its got a great wine and cocktail bar for evening tipples.

modern interiors red chair bookcase light
Malmaison

Coming en-masse with your mates? Try the Strozzi Palace Suites by Mansley, these six boutique luxury suites, located in the heart of Cheltenham town centre were built in 1894 and the stunning Grade II listed ‘Palazzo’ facade is based on Palazzo Strozzi – one of the most important examples of Renaissance architecture in Florence!

And if you’re after some country grandeur within a stone’s throw of Cheltenham book into the grand and gorgeous 5 star Ellenborough Park. This 15th century country estate gives you bags of Cotswold charm but is just over five minutes drive from Cheltenham. Bliss out in one of it luxurious suites or have a treatment in the Indian-themed spa.

WALK

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Single tree at the top of Cleeve Hill

There are some beautiful gardens to stroll around 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!). 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.

DRINK

There’s no shortage of drinking dens to dive into. We love the new for 2021 Imperial Haus, a themed cocktail bar with an enchanted forest theme, owned by Apprentice star Sophie Wilding (she made it to week 7 – not bad we reckon!). The place is awash with IG-tastic backdrops, flower walls, swings and has the most amazing cocktail menu.

Imperial Haus – the enchanted bar

Gin & Juice bar is a Muddy fave. A super-cool place for morning coffee meets, open flame-grilled food, and late night drinks. With an exceptional range of over 350 gins (and growing) you’ll be in G&T heaven. Food is served Thursday to Sunday from 12pm until 8pm, and followed by house DJ’s too. A really cool spot for the cocktail conoscenti of this spa town.

Gin & Juice bar

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. Talking of boogying the brand new Popworld has opened in the centre in 2022. If you love cheesy music this late night themed bar will be right up your street.

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.

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The atmospheric John Gordons 

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.

SHOP

shop interior dummy with hat and outfit on sitting down clothes rails wood floors lights
Inside the Bodega fashion emporium

Cheltenham is a magnet for shoppers, with the Promenade acting as its de facto King’s Road. ToastThe White Company and Hobbs and 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.

Upmarket home heaven Anthropologie has opened its doors on the Prom too, a fabulous place for gorgeous goods, and John Lewis on the High Street is a great go-to emporium for, well, everything! Check out the free personal styling sessions here too (see what happened when I went along to try one out recently.)

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 modern, edgy designs. If you’re looking for one-off, handmade designs, The Guild at 51 has just opened a brand new shop at The Rotunda. This shop-cum-gallery for the work of the Gloucestershire Guild of Craftsmen, who are a very talented bunch judging by the wares on show.

CULTURE VULTURES

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, reopening after a refurb in May 2022. 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 lived on Hatherley Road and went to Dean Close School if you want to make a rock pilgrimage, and is buried in Cheltenham Cemetery, though again, no Jim Morrison-style groupies, which is probably a good thing.

KIDS

open air swimming pool grass trees flags
Cheltenham’s open-air lido is glorious – and the water is heated!

There’s loads to do for kids in Cheltenham, from toddlers to teens – in fact it’s a real family town. 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. And recent additions include Mr Mulligans Crazy Golf which is a hoot if you’re as bad as me! The Brewery is also the place to come for all manner of kid-friendly restaurants chains, from Five Guys to Nando’s. If pizza’s your thing, then Fat Toni’s behind the Promenade is epic.

EVENTS

horses racing with jockeys
The famous Cheltenham Festival

Where to start? Cheltenham is the town of festivals – Literature, its most famous, in October (Hillary Clinton, Dawn French, Joan Collins, you name it headline here), 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 togged-up revellers. And the Food & Drink Festival in June is no small beer either. 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.

HIPSTERS

low lighting bar chairs brown
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. Prithvi is another posh hang out if you love Indian fine-dining. 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.

ON THE MOVE? 

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

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