Cheltenham is more than a gateway to the Cotswolds — it’s a town with its own vibrant personality.
Known for its regency architecture, cultural festivals, and thriving café scene, Cheltenham blends classic English charm with contemporary energy.
Whether you’re visiting for a weekend getaway or want to explore its quieter corners, this guide will help you navigate the best attractions, unique shops, and lesser-known spots that locals love.
Key Highlights
- A walk along Cheltenham’s Promenade reveals elegant regency architecture and boutique shops.
- Pittville Park offers a blend of history and open green space, perfect for a leisurely afternoon.
- Explore local markets, independent stores, and artisan cafés.
- Don’t miss local hidden gems like Suffolks Market or Winston Churchill Memorial Gardens.
- Cheltenham is a great base for short trips into the Cotswolds.
Cheltenham Racecourse and Its Racing Heritage
The heart of Cheltenham’s fame beats at the Racecourse. It isn’t just a venue for big racing events — it’s a symbol of the town’s history and culture. The Cheltenham Festival, held every March, draws fans from across the globe, transforming the town into a hub of excitement and tradition.
For those curious about the wagering side of racing, TwinSpires.com offers an easy-to-follow guide on different bet types, helping first-timers understand how this tradition intertwines with the festival’s atmosphere. Even outside the event season, a tour of the grounds or a walk through the Hall of Fame is worth it to appreciate the stories behind the sport.
The Promenade and Montpellier
Cheltenham’s town centre feels like it’s been designed for a slow, thoughtful stroll. The Promenade stands out as one of the most elegant streets in England. Tall plane trees line the avenue, while boutiques, galleries, and coffee shops offer places to pause and browse.
A natural next stop is Montpellier, an area that mixes Georgian architecture with modern lifestyle spots. It’s not just about shopping — it’s the atmosphere.
- What to look for? Beautiful caryatid-fronted buildings, alfresco dining, and terrace cafés perfect for an afternoon tea.
- Why go there? It’s a visual treat and a great area to people-watch while soaking up Cheltenham’s stylish side.
Pittville Park and the Historic Pump Room
Few places capture Cheltenham’s regency past like Pittville Park. It’s one of the largest parks in the area, with boating lakes, shaded paths, and wide lawns. The park is also home to Pittville Pump Room, a Grade I-listed gem from the early 19th century.
Visitors can:
- Taste the original spa waters (an acquired taste but part of the experience).
- Explore seasonal exhibitions or enjoy live events held inside the Pump Room.
- Simply unwind under the trees or rent a pedal boat for a relaxed lap around the lake.
The Wilson Art Gallery and Museum
Cheltenham isn’t just about outdoor spaces; it has a rich cultural layer too. The Wilson Art Gallery and Museum is a perfect stop for anyone who wants to understand the town’s character. It’s not a vast museum but strikes a balance between historic collections and contemporary exhibits.
Expect to find:
- Artwork and artefacts linked to Cheltenham’s local history.
- Pieces celebrating Edward Wilson, the Antarctic explorer born here.
- Regular rotating exhibitions featuring both local and international artists.
It’s a free entry space, which makes it easy to pop in before heading to one of the nearby cafés.
Hidden Corners and Local Secrets
The best way to see Cheltenham is often to step off the main road. There are quiet spaces and quirky finds if you know where to look:
- Sandford Parks Lido – A retro open-air pool, perfect for summer mornings. The vibe here feels almost untouched by time.
- Suffolks Sunday Market – A lively, small-scale market with artisan bread, handmade crafts, and food stalls that feel personal and homegrown.
- Winston Churchill Memorial Gardens – Smaller than the famous Pittville Park but with a calm, shaded ambiance that invites quiet moments.
- Side alleys of the Brewery Quarter – While the main area has big-name restaurants, the side streets are dotted with indie bars, small galleries, and street art.
Shopping Beyond the High Street
While Cheltenham has its share of familiar brands, what makes shopping here special are the local independents and hidden arcades. It’s worth giving yourself time to wander.
Top picks for unique finds include:
- Keith Scarrott Shoes – Known for high-quality handcrafted footwear.
- Regency Arcade – A mix of vintage treasures and local artisans.
- Bennington Street – A quieter stretch with independent interior shops and antique books.
What makes Cheltenham’s shopping scene appealing is that it’s not just about buying something but experiencing the town’s slower, more curated approach to retail.
Coffee Shops and Brunch Spots
Cheltenham has a growing café culture, with local spots that focus on good coffee and fresh ingredients. A few standouts:
- The Scandinavian Coffee Pod – Minimalist design, excellent coffee, and pastries like cardamom buns
- Brew & Bake – Great for brunch plates that feel homemade yet refined.
- Curious Café & Bistro – A cozy place with a small garden out back, perfect for a mid-morning break.
These places are not just about eating; they are little community hubs where locals gather, so they add to the authentic feel of your visit.
Quick Trips from Cheltenham
Cheltenham’s location means you can easily add short countryside adventures to your itinerary.
Recommended spots nearby:
- Winchcombe – Known for Sudeley Castle and pretty walking trails.
- Broadway Tower – A 35-minute drive brings you to one of the highest points in the Cotswolds with breathtaking views.
- Painswick – A small village often called the “Queen of the Cotswolds” for its stone cottages and beautifully maintained churchyard.
If you prefer not to drive, there are bus links and walking tour options that start from Cheltenham town centre.
Where History Meets Modern Life
The mix of regency heritage with modern events is what keeps Cheltenham fresh. Take Imperial Gardens as an example: once reserved for spa visitors, it now hosts outdoor art installations, summer concerts, and festival tents throughout the year.
The festival scene deserves a mention too. The Literature Festival is the best known, but Cheltenham also has a Science Festival and a Jazz Festival, which bring creative energy to the streets and fill the town with visitors from around the world.
Final Thoughts
Cheltenham thrives on its mix of history, culture, and small surprises. You can start the day exploring the Wilson Gallery, have lunch at a local café, spend the afternoon wandering Montpellier, and still have time for a quiet evening stroll through Pittville Park.
When thinking about things to do in Cheltenham, the magic lies in its layers: you get the polished elegance of its regency past alongside creative, modern touches that keep the town alive and evolving.