When most people think of Cheltenham, they picture race week in March – tweed jackets, champagne, and the buzz of the Gold Cup. But for locals and those in the know, Cheltenham in winter offers a different kind of magic.
Whether you’re new to the area or simply looking to make the most of the colder months, this Cheltenham lifestyle guide will show you the cosier, quieter side of town and why winter might just be its best-kept secret.
Embrace festive spirit at Cheltenham Christmas Market
No things to do in Cheltenham winter list would be complete without a visit to the Cheltenham Christmas Market.
Held along the Promenade, this seasonal staple transforms the town into a festive wonderland. You’ll find charming wooden chalets selling:
- Local crafts and artisan gifts
- Hand-poured candles and homeware
- Festive street food and mulled wine
With live music and twinkling lights, it’s perfect for a December weekend wander especially with a hot chocolate in hand. It’s also a great chance to support independent traders while ticking off your Christmas shopping.
Discover cosy cafes and winter warmers
Cheltenham is known for its elegant Regency buildings and leafy boulevards but when the temperature drops, it’s the town’s cafés and pubs that really shine.
Local favourites for a winter pit stop include:
- The Find on Regent Street – ideal for a warm brunch or a festive flat white
- Café Boho in Montpellier – great for hearty soups and homemade bakes
- The Bottle of Sauce – a lively spot with roaring fires and Sunday roasts
Whether you’re after comfort food, hot drinks or just a good book and a corner seat, there’s no shortage of welcoming places to escape the chill.
Take a winter stroll in Pittville Park
When frost coats the grass and the trees stand bare against the morning light, Pittville Park is arguably at its most beautiful.
Wrap up warm and enjoy:
- Peaceful walks around the lakes
- The crisp crunch of winter leaves underfoot
- Views of Pittville Pump Room and the historic parkland
It’s a chance to slow down and soak up Cheltenham’s natural beauty, especially rewarding after a long working week or a busy shopping trip.
Enjoy the arts without the crowds
One of the perks of Cheltenham in winter is fewer crowds at popular cultural venues. Why not explore:
- The Wilson Art Gallery & Museum – often hosting seasonal exhibitions
- Cheltenham Playhouse – with festive plays and community performances
- Everyman Theatre – showcasing pantos, musicals and national tours
The arts scene in Cheltenham thrives year-round, and winter gives you the chance to experience it at a slower, more relaxed pace.
Indulge in local food and drink experiences
Cheltenham’s dining scene continues to impress, with new independents joining established favourites. Many restaurants offer winter specials, tasting menus, or festive-themed cocktails.
Local highlights include:
- Lumière – fine dining in an intimate setting (booking essential)
- The Coconut Tree – Sri Lankan street food with a lively winter twist
- Babel – ideal for seasonal small plates and warming drinks
You’ll also find winter food festivals, pop-ups and wine tastings across town just check local listings or ask at your favourite venues.
Relax with wellness and spa escapes
Winter is the perfect time to recharge, and Cheltenham doesn’t disappoint when it comes to wellness.
- Ellenborough Park offers luxurious spa days in a country house setting
- Cowley Manor (just outside town) is ideal for a wintry weekend break
- Cheltenham Pilates & Yoga studios offer warm, gentle classes to boost your mood and energy
Whether you’re treating yourself or gifting a loved one, wellness experiences are a welcome change from the usual winter rush.
Living the Cheltenham lifestyle all year round
As a local estate agent, we know Cheltenham isn’t just a festival town, it’s a community. From family-friendly parks to foodie gems, independent shops to historic charm, this is a place that feels warm even when the weather isn’t.
If you’re thinking about making a move or investing in the area, winter is a great time to explore at your own pace. The quiet streets and cosy atmosphere offer a real glimpse of what life here is like beyond the races.
Looking to buy, sell or let in Cheltenham? Speak to the friendly team at Hunters Cheltenham, we’re always happy to share our local knowledge and help you take the next step.
