The insider’s guide to Cheltenham: The Festival Town

Come for the festivals and stay for the fun, food and fabulous hospitality: indulge your passions and experience so much more in Cheltenham.

Cheltenham, our charming Regency town, is known as the ultimate festival destination. Just a short journey from London, Birmingham, and the South West, this vibrant town boasts a packed calendar of over 35 annual festivals, making it a year-round celebration of culture, music, food, and sport. Whether you’re here for a weekend, a mid-week break, or a return visit, Cheltenham has something to offer everyone.

From iconic festivals like the Cheltenham Literature Festival - celebrating 80 years of Cheltenham Festivals this year - to the Cheltenham Jazz Festival, which attracts top international talent, this town knows how to celebrate. But the fun doesn't stop there. Cheltenham also hosts a diverse range of events throughout the year, from the Cheltenham Science Festival tackling today’s big questions, to the Gloucestershire Warwickshire Steam Railway's Cotswold Festival of Steam, featuring magnificent locomotives.

This town is also a haven for sports lovers, with the Cheltenham Running Festival offering the chance to run 5k, 10k, or a Half Marathon around the Cheltenham Racecourse. Cheltenham 7s, a festival combining sports, music, and entertainment, and the Cheltenham Cricket Festival, the world’s longest-running cricket event.

In June, the Cheltenham Food & Drink Festival at Montpellier Gardens showcases a delightful mix of live music, free wine and cheese tastings, and culinary demos from top chefs. 

New on the scene, in its second year, is the Cheltenham Fringe Festival, celebrating a range of arts from music and theatre to film and comedy. Meanwhile, the Fantasy Forest festival in July transports visitors to the world of fantasy at the magnificent Sudeley Castle.

Of course, you can't miss the Cheltenham Races, the pride of our Regency town, at Cheltenham Racecourse. Their busy calendar of jump racing action means there's always something to look forward to.

Music fans meanwhile are spoiled for choice in Cheltenham, with a packed calendar of musical festivals and performances. From Jazz and Music festivals to family-fun at Wychwood and the UK's best medium-sized music festival, 2000Trees.

Finally, new for 2025 is the Lions at Large – The Pride of Gloucestershire Trail, which will be ‘roaring’ onto the streets of Cheltenham and Gloucester this summer. Featuring 35 large Lion sculptures designed by local artists, alongside a pride of little Lions lovingly created by local schools for a fun, free and family-friendly Wild in Art event.

Images - Fantasy Forest, Lion's at Large, Cheltenham Jazz Festival

Fuel Your Passion: Dining at Cheltenham’s Best Festival Spots

Cheltenham’s festivals are complemented by its eclectic food scene, offering a variety of dining options that cater to all tastes. Whether you're looking to indulge before or after a festival, you'll find plenty of places to satisfy your cravings.

Start your festival dining experience at The Nook on Five, Cheltenham’s only rooftop bar and restaurant, located in Imperial Square. With stunning views and a refined dining atmosphere, it’s a perfect spot for festival-goers. Meanwhile, Sef Steakhouse, just below the Nook, is the ideal spot for meat lovers with a refined palette. Settobello, meanwhile, just across the road, is great for a more laid back atmosphere.

Pho in the Brewery Quarter brings the vibrant flavours of Vietnam to life, while Kibou on Regent Street serves up Japanese delights in a lively setting—both are family-friendly with kids' menus.

For a truly iconic Cheltenham experience, head to The Ivy, an elegant brasserie found in a Grade I-listed building. Whether you're enjoying modern British or international classics, this spot is a must for visitors during the Cheltenham Jazz and Literature Festivals.

If you're in the mood for something more relaxed, enjoy The Tavern in Royal Well Place, where you’ll find delicious seasonal food in a lively atmosphere. Or, for a fun, casual bite, check out The Beefy Boys in Regent Street, known for their indulgent American-style ‘dirty’ burgers and cocktails.

Images - Nook on Five, top Pho, bottom The Beefy Boys

Rest Up in Style: Stay in Comfort and Convenience

After a day of festival fun, relax and recharge in one of Cheltenham’s many excellent accommodations, from luxurious hotels to charming boutique stays.

Stay at the Queen’s Hotel, one of Europe’s finest, overlooking the beautiful Imperial Gardens. This elegant hotel is ideally located for those attending events in the town centre. No 38 The Park is a stylish, dog-friendly boutique hotel located in the leafy Pittville area, offering easy access to Pittville Pump Room and the town centre.

For a more immersive experience, consider Ellenborough Park Hotel in Southam, a luxury hotel nestled between the Cotswolds' highest point and Cheltenham Racecourse, perfect for attending the Cheltenham Festival in March or the Wychwood Festival in June. With their new Lodge accommodation, it's truly a home away from home.

Other great options include Malmaison, close to Montpellier-based festivals, the centrally-located The George Hotel, and the Holiday Inn Express, just a stone's throw from The Brewery Quarter and their Summer Jam. If you’re after a more rustic experience, check out the glamping and camping options at Cotswold Farm Park near Guiting Power, or StarGlamping up Leckhampton Hill.

Images - Queens Hotel, top Ellenborough Park, bottom The George Hotel

Explore Cheltenham Beyond the Festivals

Cheltenham is not just about festivals—there’s plenty to explore beyond the crowds. Take a stroll through Pittville Park & Pump Room, where the town’s spa heritage began during the Georgian era. For a dose of culture, catch a performance at the Everyman Theatre or Playhouse, both offering a wide range of dramas, comedies, and musicals. Art lovers can explore The Wilson, Cheltenham’s renowned gallery with rotating exhibitions.

Shopping in Cheltenham is another highlight. Walk along the Promenade, lined with international retailers, or discover independent gems in Montpellier and The Suffolks, home to unique shops like Bodega, Pink Vintage, and the Gloucestershire Guild of Craftsmen. For those who appreciate fine jewellery, Cheltenham boasts a variety of artisan and bespoke designers.

The Perfect Festival Destination

Cheltenham truly earns its title as The Festival Town, but with so much more to offer, it's worth extending your stay to enjoy everything this vibrant destination has to offer. Whether you’re indulging in world-class food, exploring its rich cultural offerings, or relaxing in luxurious accommodations, Cheltenham is the place to be for unforgettable experiences.

Come for the festivals, stay for the fun, food, and fabulous hospitality—Cheltenham awaits!

To plan your stay in Cheltenham check out our helpful guides...

See all of the festivals & events coming to town this year - Cheltenham Festivals Guide

For more food inspiration, visit - Cheltenham restaurants, Cheltenham cafes, pubs and bars in Cheltenham.

Visitors, you may find our map of Cheltenham handy