Cheltenham, often celebrated for its lively calendar of festivals — from the famed horse racing in March to the Literature Festival in October — is much more than just an event hub. Recently ranked as the second-best among the UK’s largest towns by The Telegraph, Cheltenham earned an impressive 9 out of 10 from Destination Expert Chris Moss. While seaside town Blackpool edged it out with a 9.5, Cheltenham proudly claimed the title of the ‘poshest’ town, thanks largely to its elegant Montpellier district and the historic, airy Promenade shopping avenue dating back to the 1820s.
What creates this aura of poshness? Is Cheltenham truly as upscale as its reputation suggests?
Arriving on a sunny spring Monday, Cheltenham immediately captivates with its well-preserved Regency architecture — sash windows, ornate ironwork, and stately water features — and expansive green spaces like Imperial Gardens, Montpellier Gardens, and the larger Pittville Park. The town is widely regarded as Britain’s most complete Regency town, a distinction visible in every graceful street and square.
READ MORE: Residents Demand Urgent Improvements to Cheltenham-Gloucester 97/98 Bus Service
READ MORE: Dom Joly’s Favourite Pub: Cheltenham’s Best-Kept Secret
Imperial Gardens welcomed me first, where a towering 36-metre Ferris wheel offered sweeping views across Cheltenham and the surrounding Cotswold hills. For just £6, two rides provide a refreshing perspective — though the wind up top might not suit everyone. The blooming spring flowers and ample benches create a peaceful retreat in this beloved park space.
Locals May and Maria, enjoying the sunshine, shared their thoughts on living in Cheltenham. Maria praised the town’s vibrant social scene and outdoor activities, noting its festivals, popular races, excellent restaurants, and proximity to nature, like nearby hikes on Cleeve Hill. May highlighted the town’s safety, cleanliness, and convenient connections to London and the Cotswolds, making Cheltenham an attractive and accessible home.
Cheltenham resident Rob acknowledged the town’s increasing poshness, influenced by the rising appeal of the Cotswolds lifestyle, but emphasized its welcoming, traditional atmosphere. “It’s a great place to just relax and enjoy a stroll,” he said, hopeful the town retains its charm.
Not all residents share this glowing view. Charlotte, who has lived here for seven years, described Cheltenham as “pretend posh” and “soulless,” criticizing its limited activities beyond dining and drinking. She observed an influx of average coffee shops and lamented the difficulty newcomers face in breaking into local social circles. To her, the posh reputation inflates prices without delivering sufficient value.
To explore this divide, I ventured into Montpellier’s ‘posh’ heart. Unlike the bustling High Street and Promenade filled with chain retailers like Waterstones and Charles Tyrwhitt, Montpellier thrives with independent boutiques, galleries, and quaint cafés. A hidden gem, The Courtyard arcade hosts unique specialty shops—a tattoo studio, kitchenware store, and fashion boutique—though many were closed on the quiet Monday I visited.
Kathryn Clarke, an artist who journeys weekly from nearby Stroud to sell her crafts in Cheltenham, praised Montpellier’s village-like community feel and tidiness. She contrasted it with the scruffier atmosphere of Stroud, noting the evident affluence in Cheltenham’s streets despite some doubts about its posh image.
Despite missing out on visiting The Wilson art gallery due to its Monday closure, I ended my day at Sandford Park Alehouse on the High Street. Known as one of comedian Dom Joly’s favourite pubs, its sunny beer garden and relaxed vibe offered a perfect spot to reflect on my visit.
Cheltenham surprised me with its layers beyond the familiar high street brands and seasonal events. It’s a town woven with tradition, green spaces, and local culture — balancing its reputation for elegance with everyday appeal. I look forward to returning on a busier day, eager to experience Montpellier fully alive with visitors and discover even more of what makes this Regency gem so distinctive.