Things to Do in Cheltenham: Culture, Cafes & Countryside Strolls
Cheltenham offers a unique blend of Regency elegance and modern energy. This stylish town is famed for its graceful 19th-century architecture and tree-lined avenues, yet it pulses with contemporary creativity. Visitors find a thriving independent spirit here – from boutique shops and chic cafes to arts festivals and innovative galleries – all set against the backdrop of a historic spa town.
Whether you're looking for unusual things to do in Cheltenham, fun experiences for adults, or romantic activities for couples, this guide covers the best of what this Regency town offers. Perched on the edge of the Cotswolds, Cheltenham charms with culture and countryside in equal measure. With Malmaison's boutique hotel right in the town centre, you have an elegant home base that matches Cheltenham's confident, polished vibe.
Why Cheltenham should be on your radar
Cheltenham has transformed from a genteel Regency spa retreat into a vibrant modern destination without losing its historic charm. The Promenade, one of the UK's finest shopping boulevards, is lined with leafy trees, elegant cafés and Regency facades. Immaculately preserved 18th- and 19th-century buildings with stucco fronts and wrought-iron balconies recall an era of aristocratic leisure.
Beyond its architecture, Cheltenham stands out for its thriving independent scene. You'll discover countless one-of-a-kind boutiques, artisan markets and friendly coffee shops instead of cookie-cutter high street chains. This independent ethos extends into a lively collection of bars and brasseries that stay buzzing after dark, giving Cheltenham a cosmopolitan flair.
Often called the gateway to the Cotswolds, it's perfectly positioned for exploring England's most picturesque villages. Chocolate-box villages like Bourton-on-the-Water, Stow-on-the-Wold, and Broadway are just a short drive away. Direct trains from London reach Cheltenham Spa in under two hours, and the town is just off the M5. Unlike over-crowded tourist hubs, Cheltenham remains relaxed and spacious, offering refined culture and natural beauty without the hassle.
Things to do in Cheltenham for couples and culture lovers
Cheltenham hosts four major festivals – Literature, Music, Science and Jazz – that draw talent and audiences from around the world. During festival season the town buzzes with creative energy: renowned authors in conversation, live jazz in the parks, cutting-edge science demos, and classical concerts in historic halls. Much like Edinburgh's famous festival scene, Cheltenham transforms during its cultural celebrations.
Year-round, the Everyman Theatre, a gorgeous Victorian venue, offers everything from West End musicals to comedy. The Wilson (Cheltenham's Art Gallery & Museum) boasts an internationally renowned Arts and Crafts Movement collection with free admission. The Pittville Pump Room, opened in 1830, is the grandest surviving spa structure from Cheltenham's heyday, hosting concerts and events in stunning Regency surroundings.
Festival season in Cheltenham
If you can time your visit with one of Cheltenham's festival periods, you'll experience the town at its best. Late April brings the Jazz Festival, followed by the Science Festival in June, Music Festival in July, and the famous Literature Festival in October. During these events, green spaces fill with tents, stages, and excited festivalgoers. Hotels and tickets book up quickly, so plan ahead and secure your accommodation early – Malmaison Cheltenham makes an ideal base for festival-hopping.
Shopping the independent way
Cheltenham invites you to shop at a gentler pace. Start in Montpellier, where fashionable boutiques, galleries and patisseries occupy beautiful Regency buildings. Don't miss the Montpellier Caryatids – sculpted female figures inspired by classical Greek statues that hold up shop fronts along Montpellier Walk.
The Suffolks feels like a hidden village within the town. Centered around Suffolk Square's grand terraces, this area is known for antiques, vintage finds, and specialist stores. You might browse an artful interiors boutique, a second-hand bookshop, or a local designer's studio. On certain Sundays, The Suffolks hosts street markets with independent stallholders.
Whether you're hunting for a unique antique or window-shopping, Cheltenham's elegant setting and laid-back vibe turn a simple shopping trip into a quintessential experience. For evening entertainment, independent wine bars and characterful pubs provide sophisticated gathering spaces – perfect for adults seeking quality over generic nightlife.
Cheltenham's food and drink scene
Cheltenham appreciates good food, stylish surroundings, and memorable dining experiences. At the heart of it all is Malmaison Cheltenham's brasserie and bar. The brasserie delivers bold, modern British dishes with a focus on flavour, seasonal ingredients, and confident cooking. From indulgent breakfasts to elegant dinners, the menu suits every point of the day.
The bar is equally inviting – perfect for a pre-dinner cocktail, celebratory champagne, or late-night nightcap. With plush interiors and a curated drinks menu, it's a destination in its own right. Guests often find that once they settle in, there's little reason to go anywhere else.
Cheltenham is also home to Hotel du Vin Cheltenham, another popular choice for those looking for a refined dining experience. Known for its classic French-inspired bistro menus and impressive wine selection, it offers traditional elegance with a strong focus on wine. Current food and drink offers range from prix fixe menus to wine pairing experiences, making it a great option for those who enjoy timeless flavours and expertly curated wine lists.
Together, these two hotels shape much of Cheltenham's upmarket dining identity. Both offer polished settings, confident menus, and an emphasis on experience as much as flavour. Whether you prefer Malmaison's bold, contemporary style or Hotel du Vin's classic elegance, you'll find that Cheltenham's best dining experiences are about more than just food – they're about atmosphere, service, and making an occasion out of every meal.
Regency architecture and elegant strolls
One of the simple pleasures of Cheltenham is wandering its beautiful streets and parks, admiring some of the finest Regency architecture in Britain. Begin with a gentle stroll down The Promenade, the town's showpiece avenue. Laid out in the early 19th century, the Promenade remains breathtaking with its wide pathways, trees, and grand buildings. Look out for Neptune's Fountain and the whimsical Hare and Minotaur sculpture.
From the Promenade, head to Montpellier Walk to see those famous Caryatid statues up close. The Imperial Gardens showcase over 25,000 bedding plants each year in neat, colorful arrangements. Framed by the majestic Cheltenham Town Hall, Imperial Gardens is a favorite spot to relax among the blooms.
Green spaces and the Cotswolds connection
Cheltenham is dotted with parks perfect for unwinding. Pittville Park stretches over 100 acres with graceful lakes and meandering paths. There's even a boathouse where you can rent a rowboat. Sandford Parks Lido offers a 1930s outdoor pool set in landscaped gardens – perfect for summer swimming.
As the gateway to the Cotswolds, Cheltenham is ideal for day trips into one of England's prettiest regions. In less than half an hour, you can be among rolling hills and storybook villages. Walking enthusiasts will find trails on the Cotswold Way, including Cleeve Hill, which rewards with panoramic views. From cultural festivals to countryside walks, there are plenty of things to do in and around Cheltenham throughout the year.
Racing heritage and sporting tradition
Cheltenham lives and breathes horse racing, most notably during the Cheltenham Festival each March – the pinnacle of the jump racing calendar. The festival's climax is the Gold Cup, Britain's most prestigious jump race. The whole town takes on a lively, celebratory mood during race week.
If you plan to attend the Festival in March, make arrangements well ahead – tickets and hotel rooms (including at Malmaison) can be scarce. But outside of racing season, you can still visit the racecourse or pop into racing-themed pubs to sense the town's pride in this sport.
Seasonal experiences worth planning for
Spring: Festival season kicks off with Jazz in April and Science in June. Parks erupt in bloom with tulips and cherry blossoms lining the avenues. March's Gold Cup week is thrilling but book early.
Summer: Outdoor events fill the calendar. Enjoy swimming at Sandford Parks Lido or alfresco drinks on sunny terraces. The Music Festival brings performances to historic venues.
Autumn: The Literature Festival in October draws big-name authors. Turning leaves paint the town gold and crimson, creating perfect conditions for cosy cafes and bookshop browsing.
Winter: Christmas lights sparkle along the Promenade, markets offer seasonal treats, and you can ice-skate in Imperial Gardens. The Everyman's pantomime and special concerts add festive cheer.
Where to stay in Cheltenham
Malmaison Cheltenham blends the town's Regency charm with bold boutique design. Housed in a striking white Georgian villa with contemporary extension, the hotel offers sleek interiors and artful touches that create luxury with personality.
The location is perfect: minutes on foot from the Promenade's shops, Imperial Gardens, and Montpellier's boutiques. After exploring, unwind with a craft cocktail in the bar or savor a meal at the brasserie. Special packages are often available, from weekend deals to seasonal promotions. In a town known for refinement, Malmaison captures Cheltenham's essence: elegant, vibrant, and delightfully individual.
FAQs
What are the main things to do in Cheltenham?
Cheltenham offers cultural attractions including festivals, theatres, and galleries, elegant Regency architecture, independent shopping in Montpellier and the Suffolks, a thriving food scene, beautiful parks and gardens, and easy access to the Cotswolds countryside. The town's famous racecourse hosts the prestigious Cheltenham Festival each March.
Is Cheltenham worth visiting?
Absolutely. Cheltenham combines Regency elegance with vibrant contemporary culture, offering sophisticated experiences without the crowds. The town's independent spirit, cultural calendar, architectural beauty, and position as gateway to the Cotswolds make it ideal for weekend breaks and longer stays.
How long should I spend in Cheltenham?
A weekend gives you time to explore main attractions, enjoy the dining scene, and take a Cotswolds day trip. Longer stays allow for festival attendance, more countryside exploration, and deeper appreciation of Cheltenham's cultural offerings.
What is Cheltenham famous for?
Cheltenham is renowned for its Regency architecture, the prestigious Cheltenham Festival (horse racing's premier event), vibrant festivals including Literature, Music, Science and Jazz, and its position as gateway to the Cotswolds. The town has a strong reputation for culture, independent businesses, and refined living.