A weekend in Cheltenham: A 48-hour itinerary

From an 18th-century spa destination to a modern festival town, my home town of Cheltenham can sometimes get overshadowed by its more touristy neighbours – with Oxford on one side, Bath on the other and picture-postcard Cotswold villages surrounding it. But Cheltenham has lots to offer as a weekend break destination in its own right. There’s gorgeous Georgian architecture, pretty parks, festivals dedicated to everything from music and literature to wellbeing and horse-racing, plus an impressive array of places to eat, drink and shop. So here’s my 48-hour itinerary for how to spend the perfect weekend in Cheltenham.

Read more: 10 Great British weekend break ideas

How to spend a weekend in Cheltenham

Montpellier Gardens

Friday evening

Check in to the Malmaison Cheltenham, located in the heart of Montpellier – Cheltenham’s most stylish district, surrounded by bars, restaurants and boutiques. Set in a white Regency villa, the hotel is classically grand from the outside but inside it’s modern and stylish, with lots of contemporary furniture and artworks, and modern tech like paperless check-in and in-room iPads. There’s lots of space to relax, with a cosy lounge-come-library and a Victorian conservatory as well as a smart bar, restaurant and spa. Double rooms from £119 a night.

Take a walk through Montpellier to the Daffodil for dinner. The restaurant serves modern British food in a converted art deco cinema, full of gorgeous original 1920s design features. Head upstairs for a drink in the Circle Bar first, with a great cocktail list and half-price bubbly on Fridays from 12pm. Then walk down the sweeping stairs to the restaurant – where the original cinema screen used to be you can now watch the chefs in action in the open kitchen.

Art deco style at the Daffodil

Saturday morning

Start the day off with a walk through Montpellier and Imperial Gardens. Cheltenham is a big festival town and the parks are used as venues for annual jazz (May), science (June), food (June), music (July) and literature (October) festivals. But even if you’re not there for a festival, you can grab a coffee from one of the park cafés and take a walk around the gardens. Carry on down the Promenade, Cheltenham’s main shopping street lined with elegant Georgian buildings.

The Neptune Fountain on Cheltenham’s Promenade

To learn more about Cheltenham, join a history and architecture walking tour. The Blue Badge guides have lots of interesting stories about the town’s Regency buildings and its days as a holiday destination for upper-class spa-goers. Tours start from the Wilson gallery and museum at 11am on Saturdays from April until October and last 90 minutes (adults £6, under 16s £3).

At the end of the tour, head back to the Wilson for a look around the galleries. There’s a real mix of exhibits, from Arts and Crafts furniture and Dutch and Belgian paintings to the story of local hero Edward Wilson – one of Scott’s team on his ill-fated 1912 Antarctic expedition.

The Wilson Art Gallery and Museum

Saturday afternoon

Refuel with a stop at the Well Walk Tea Room for afternoon tea. It’s one of Cheltenham’s oldest shops and is packed with quirky antiques and their cakes are served on a selection of pretty vintage crockery. Don’t miss a Cheltenham Dripper – a sweet and sticky pastry which was originally made with beef dripping and is the local version of a lardy cake.

Walk it off with a trip to Pittville Pump Room, 15 minutes north of town. Built in the 1820s, it was Cheltenham’s largest spa building and is surrounded by manicured lawns and ornamental lakes. You can still taste the medicinal spa waters (open 10am–4pm, unless an event’s on).

Start the evening with a pre-dinner drink. If you’re a real ale fan, pop into the Jolly Brewmaster for a pint, a traditional-style pub with a great selection of beers on tap and a big beer garden for summer nights. Or if gin’s more your thing, head to Gin & Juice at 131 The Prom, where they have over 350 different gins on the menu. Then have dinner at Koj, a Japanese restaurant that specialises in sharing dishes (and doesn’t do sushi) run by a MasterChef finalist. Their upstairs Bandana Monkey Bar is a good place to finish the night with a sake or shochu.

The Pittville Pump Room

Sunday morning

If the sun’s out (or you’re feeling brave), start the day with a few laps at Cheltenham’s 1930s Sandford Parks Lido. At 50 metres long it’s one of the UK’s largest outdoor heated pools and also has childrens’ pools (adults £5.50, concessions £3.50). If that sounds too energetic, spend the morning unwinding at Chapel Spa with a massage, facial or body scrub. Then head to the Bottle of Sauce for brunch, with everything from breakfast butties to chicken n’ waffles.

If you’re in the mood for shopping, you’ll find the usual high-end, high-street shops (think White Company and Space NK) on Cheltenham’s Promenade. Or the area around Montpellier and the Suffolks has lots of interesting independent shops. Check out the Triton Gallery for antiques and interiors inspiration, Bodega for women’s fashion, David Hayward for bespoke jewellery, Curious City Print Shop for quirky artwork and the Suffolk Anthology book shop.

Shopping in Montpellier

Sunday afternoon

Cheltenham is surrounded by gorgeous countryside, so head out of town to get a taste of the Cotswolds to finish off your weekend. Cleeve Hill is just a few miles out of Cheltenham (a short car or bus ride on the 606 service) and is where you’ll find the Rising Sun, a good spot for Sunday lunch which has fantastic views across five counties from its beer garden.

Then head out on a post-lunch walk, following a loop around Cleeve Hill. The walking route runs for four or six miles up through woodlands and meadows, with panoramic views across the Cotswolds, to Gloucester Cathedral and right across over to the Black Mountains in Wales. It’s part of the Cotswold Way, a 100-mile walking route from Chipping Campden to Bath.

Cleeve Hill views

Have you visited Cheltenham? Do you have any tips to add on what to see, do and eat?

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