Compact and characterful and filled with a whole lotta fun, Chester is the city break hidden right under your nose. Behind the postcard-perfect façade is a city quietly flexing its cool credentials that go far beyond a trip to the zoo and the racecourse (although they’re definitely worth exploring). Where underground wine bars in 13th-century cellars rub shoulders with cult coffee haunts, and shoppers hunt down under-the-radar indie shops before chasing cocktails in candlelit jazz bars. Whether you’re here for a weekend wander or a full-blown retail therapy pilgrimage, we’ve sniffed out the best of Chester — time to dive in.

FIRST UP, COFFEE

Caffeine fix calling? Potter on over to Jaunty Goat where locals order top-tier espresso in a space of slick Scandi interiors. Bean & Cole is a local favourite for a reason: strong brews, laid-back vibes, and dreamy cinnamon buns. Over by the cathedral, The Flower Cup pairs artisan coffee with lush, leafy interiors – part café, part houseplant haven. And tucked in the Rows, Short + Stout serves up proper speciality coffee with zero pretension.

DO

One of the things I love about Chester is that it’s all so compact. Which makes it the perfect subject for a foodie tour. Enter Chester on a Plate tours, launched only last year by Stephanie Bath, who’s hugely passionate about the city’s indie food scene. Using her on-the-ground-intelligence, she’s curated a collection of tours, from street food to cheese and wine, and a brewery tour of the city. Though a good intro is the half-day tour, making pit-stops at indie bars and restaurants that aren’t revealed until you arrive. Just don’t forget to pull on your fat pants.

A cathedral to culture housed in a converted 1930s cinema, Storyhouse is Chester’s beating creative heart. It’s a café, a cinema, a library, a bar, and a performance space all rolled into one slick, Scandi-chic venue, buzzing from morning lattes to late-night curtain calls. Expect everything from boundary-pushing indie productions to big-name touring shows, open-mic nights, bookish happenings, and film screenings that go way beyond the blockbusters. Chic, community-driven and gloriously unpredictable. I’m always writing about Storyhouse in our what’s on guide, as there’s no doubt it puts on some of the biggest theatre productions in the county.

Or how about an after-dark tour of Chester – apparently one of Britain’s most haunted cities. After sunset, you’ll follow a costumed guide through shadowy alleys, for tales of ghostly monks, headless equestrians, and sinister happenings lurking behind Tudor façades. This 90-minute nocturnal labyrinth of chilling history starts outside the Town Hall every weekend – Fridays and Saturdays in summer, with extra scares at Halloween. At just £10, it’s a jump-scare of culture worth every penny.

Head to hipster event space Carriage Shed over the weekend, where there’s always something interesting and cool happening, from vintage markets to festivals. What’s on for autumn? How about the free, dog-friendly Chester Food and Craft Festival (13 Sep). Expect artisan homewares, unique crafts, and street food stalls – plus live local music and independent makers everywhere you look. In fact, there’s one in Oct and Nov too if you can’t make this September shindig. From 10am-4pm.

Fancy a break from the buzz? Then it’s gotta be a wander around Grosvenor Park. This green sprawl, just beyond the city walls, is a Victorian pleasure garden, where locals flop on picnic blankets during the warmer months, or grab coffee as the weather turns from bakery and brunch spot, Fika, before plodding around its sweeping lawns. In summer, it transforms into the stage for leafy outdoor theatre – ideal for catching Shakespeare under the stars. Even without a show, it’s the ultimate mid-afternoon reset and perfect for a spot of people-watching.

Or how about walking along the city walls? An absolute rite for passage for anyone visiting Chester, this ancient Roman relic is the only full city wall circuit left in Britain. Take the full loop (a mellow 2 miles), where walkers can gaze across to cathedral towers, secret gardens, Tudor rooftops, and the odd pub courtyard you might just have to hunt down. Go early for golden light, or sunset for full romantic drama.

Chester Cathedral. Gareth Rainsforth — Gareth Rainsforth

Gazing at the cavernous atrium of the city’s cathedral is worth your while, but for an added bonus, book a behind-the-scenes tour, slipping away from the mulling crowds and towards its hidden curiosities. Gather in the bell-ringing chamber and stare at the complex stained glass windows, wandering along the darkly magical corners of the galleries. At the climax is a 200-step staircase towards the lookout tower, where you can scan the city from on high and, on a clear day, catch sight of the distant Welsh hills.

Chucking it down? Head inside and to Breakout – a thoroughly amusing escape rooms, where visitors fight against the clock to break out of its seven themed rooms, from a forgotten tomb to a secluded and sombre cabin in the woods.

EAT

Make sure the epic emporium of Chester Market is the first foodie spot on your list. Having reopened in 2022, it brings together a whole hoard of foodie traders under one roof. There are of course the stalls where locals pick up fruit and veg and stock up on fish for the week. But the true joy of the place is in ordering a wine or three and mulling over the steaming pots of curry, the piles of pasta or the French-inspired bakes from Pastry Pedaleur.

Elsewhere, Chef’s Table has garnered a reputation for exquisite contemporary cooking led by chef Liam McKay. The same team are also behind Twenty Eight sitting next door, an innovative borne-out-of-lockdown space dishing up British-style plates using produce plucked from Growing @ Field 28. My tip? Head to Twenty Eight at lunch to take advantage of its banging deal: two courses for £28 with starters such as sourdough crumpet with Cornish crab and pickles, or trout in a fennel and almond gazpacho, and mains, including rabbit leg pie with tarragon mustard sauce. Yum!

A must from the people who conjured Manchester success story, Climat, Covino is a compact wine bar and restaurant on Northgate Street, where diners fawn over seasonal small plates all washed down with organic wines. The food is outstanding but its wine game is seriously next-level, with over 130 international labels filling the chalk‑scrawled shelves.

I am a huge fan of Porta – the wildly popular tapas enterprise with spaces in Altirncham, Chester, Salford and West Didsbury. So I’m wholeheartedly excited about the visionary team’s new opening: The Jolly Gardeners — a spruced-up pub with serious pedigree and zero pretension. Behind the scenes, the same dream team who mastered the art of casual fine dining at Porta are pushing boundaries, pouring their signature flair into this fresh venture and transforming local, seasonal ingredients into plates with comfort and edge with a charcoal grill at the centre of it all. Expect dishes such as brown crab risotto, grilled spatchcock poussin with aioli, and asparagus in smoked crème fraîche and wild garlic. No fancy foams, no gel-like concoctions. Just a smart, spirited spot to gather, graze, and sink a few drinks in a space that effortlessly transcends the familiar pub grub cliché.

A fresh wave has hit Chester’s dining scene with the arrival of The Sandbar, a sleek new restaurant from Martin Taylor, the chef behind the much-loved seafood shack in New Chester Market. Opened on Watergate Street, The Sandbar reimagines Taylor’s coastal street-food roots into a relaxed yet refined dining experience, where breezy and minimalist interiors echo Cornish coastal charm with Nordic restraint. Menus shift daily, showcasing whatever’s been scooped from local hauls – from whole grilled fish filleted at the table to shucked oysters and Shetland octopus. And the theme? Unpretentious, effortlessly stylish, and deeply rooted in its city – I’m certain it’ll morph into Chester’s go-to coastal fix (no trip to the seaside required).

And finally, there’s Stile Napoletano – a true revelation, having been crowned the 13th best pizzeria in Europe (yes, Europe, not just the UK), as well as finding itself in The Good Food Guide 2025. Run by Giacomo Guido from the heart of Naples, Stile’s pizzas are an unapologetic love letter to tradition, crafted from slow-fermented dough which magnificently holds up under a flood of molten mozzarella and exquisite toppings.

DRINK

Sprucing up the rooftop of Pepper Street car park, Rooftop Social Club is Chester’s sky‑high playground. Two levels of social magic unfold under a retractable roof, with heated cabanas, chalets, and killer views. A handful of permanent kitchens take care of the food, including Death by Tacos, The Fat Greek, and Enzo’s Pizza. Add in games (cornhole, shuffleboard, table tennis), seasonal pop‑ups, and craft cocktails, and it’s your year‑round hangout to play, sip and eat.

And then there’s Metronome Jazz Bar. A moody, intimate, vinyl-spinning jazz bar that feels like a New York loft. Expect flickering candles, smooth tunes, and epic cocktails.

SLEEP

From grande dames to design-led pads, Chester has plenty of gorge boltholes to rest your head. Though for something entirely different, you might want to take a look at unique Airbnbs in Cheshire or nearby dreamy glamping spots.

Perched canal‑side, Moxy Chester mixes industrial‑chic flair with cheeky comfort. Check‑in happens at the bar (cocktail in hand), and the lobby doubles as a hangout‑meets‑co‑working zone with video walls, plug‑in stations, pool tables and photo‑booths. Rooms are smart, compact, and loaded with charging ports and flat‑screens. Best bit? It’s pet‑friendly if you don’t want to leave your furry friend behind.

Fancy a bit of whimsy? Then you’ll want to bed down in Oddfellows Chester – a boutique townhouse hotel, where maximalist interiors meet Cheshire cool. It’s a little like falling through the rabbit hole with upside-down furniture, extravagant wallpaper, clawfoot tubs in bedrooms, and punchy cocktails on the secret garden terrace.

If it’s five-star grandeur on your wishlist, look to The Chester Grosvenor – a grande dame slap bang on Eastgate Street. It’s the sort of place top-hat-wearing doormen usher you inside, where plush rooms open to killer views across the city, and guests potter around the bar for Champagne and chef‑curated, 3‑AA‑Rosette fine dining in Arkle. Oh and there’s a gorge spa too.

Hotel Indigo is a design-savvy boutique with nods to Chester’s character – choose from rooms themed on the Eastgate Clock, racecourse, or the city’s architecture, all featuring Hypnos beds, spa-style rainfall showers, and luxe Zenology toiletries. And you have to bag a table at The Forge, bringing open-fire cooking, provenance and AA‑Rosette pride to this corner of the city.

SHOP

Born from a pop‑up experiment, Styled Boutique remained popped up on St Michael’s Row with a very affordable streetwear edit and casual must-haves for every season. Keep an eye on their Instagram for their latest collections, but trust me, once you’re inside, you won’t be coming out for a while. Elsewhere there’s Lee Louise – a colourful emporium stacked with gifts, jewellery and tribal-type clothing amid the swirl of incense. Chester’s real-life Aladdin’s cave – set in a Grade II listed building perched on stilts since 1571.

All that shopping and boozing getting to you? Better head on over to The Scented Garden Retreat – a tucked-away spa on Northgate Street Row, where serene seekers escape the city and book in for bespoke aromatherapy, facials and holistic therapies in soft‑lit, candle‑lit rooms. But it also has a dreamy shop with eco‑chic, cruelty‑free skincare – from Dermalogica to essential oils and indulgent bath treats.

And inside the storied Chester Rows, where architectural heritage meets Insta-worthy shopping, you’ll find The Antiques Shop, run by the same family for nearly 30 years. We’re talking British antiques – whether you’re on the lookout for a clothes horse, vying for a rocking chair or just keen to have a good ole rummage.

In the mood for more? Here you go…

Where to eat, drink, shop + stay in the Northern Quarter

The 5 best places to travel in Europe this September

The best things to do in Cheshire

Why Chester is the underrated city break for your bucket list

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