Cheltenham
At Your Leisure Volume 7
Cheltenham is where Regency grandeur meets a modern, high-octane cultural pulse. Less sleepy spa town, not a Cotswolds village – Cheltenham is a style-conscious powerhouse that hums with creative energy, world-class festivals, and effortless flair.
By Charlotte Ellis.
Time to discover
Cheltenham is visually striking; sweeping crescents, ironwork balconies, and grand parks frame an architectural dreamland that feels entirely intimate and walkable—designed for effortless discovery.
The chic Montpellier district reveals the town’s historic spa roots. Here, high-end boutiques and contemporary concept stores sit comfortably alongside independent coffee shops, artisan bakeries, chic wine bars, and glamorous eateries. The wide, tree-lined promenades add a distinct sense of elegance that naturally invite you to slow down and savour the surroundings.
Cheltenham’s modern identity is defined by its arts scene, legendary festivals, and vibrant weekend energy. Plan your visit around its stellar calendar—whether it’s the world-famous Literature Festival (October), the Jazz Festival (April/May), or the Science Festival (June), the town transforms into an electric hub for thinkers, creators, and culture lovers.
As one of the region’s architectural jewels, the Everyman Theatre is a masterpiece of Victorian design brought to life by legendary architect Frank Matcham*. Step inside to experience an impressive auditorium featuring ornate gilding, plush velvet, and a vibrant year-round calendar spanning West End productions, comedy, and cutting-edge drama. Arrive early to grab a pre-show cocktail in the foyer bar (discover more at everymantheatre.org.uk). Be sure to also check out the Town Hall for its own impressive roster of entertainment and events.
Weekending in style
Morning: Kick-start your day with exceptional coffee from Montpellier’s knockout spots, such as For The Saints Espresso Bar, before hitting The Promenade. Pair high-end flagships with chic luxury independents, antique and art dealers, wellness spaces, and gorgeous lifestyle concept stores for serious retail therapy.
Midday: After shopping, head to The Quadrangle to refuel. Choose between the wood-fired, Naples-style brilliance of Bosco Pizzeria or the sophisticated cuts at Sef Steakhouse.
Afternoon: Spend your afternoon exploring cutting-edge local and national collections at The Wilson Art Gallery and Museum. For a sweet afternoon pick-me-up, stop by out The Clementine Café for artisan treats and homemade Italian gelato.
Evening: Head back to your boutique quarters — such as : The Queens Hotel, No. 131 or Hotel du Vin — to freshen up for the evening. Start your night with panoramic rooftop drinks at The Nook at no 5 before heading to Lumière. Tucked away on a quiet residential street, this independent, Michelin-starred restaurant delivers an unforgettable, hyper-seasonal tasting menu celebrating the very best of British produce. Expect immaculate service and an intimate atmosphere.
Nightcap: Conclude the evening at Gin & Juice (located within No. 131), where a sleek crowd, late-night energy, and a collection of over 400 gins await.
More Ways to Experience Cheltenham
- Wellness & Re-alignment: Surrender to complete relaxation at Koco Bloom, a luxury holistic sanctuary offering restorative treatments, dynamic mat Pilates, and sound bath sessions.
- The Pittville Park Stroll: A quintessential 2-mile, easy-going walk taking you past ornamental lakes, expansive lawns, and the magnificent, Grade I listed Pittville Pump Room.
- The Sporting Life: Check the seasonal fixture list at the iconic Cheltenham Racecourse.
- Step Back in Time: Take a scenic ride on the heritage Gloucestershire Warwickshire Steam Railway (GWSR).
- Get Competitive: With two Roxy Lanes and a Flight Club in close vicinity it’s a great chance to get your competitive head on and have a giggle.
*Frank Matcham (1854–1920) was Britain’s most prolific and celebrated theatre architect, responsible for designing or refurbishing over 150 buildings across the United Kingdom during a 40-year career.