Cheltenham's Festivals

Cheltenham's Festivals

Located on the outer fringes of the Cotswolds AONB, the Regency town of Cheltenham in Gloucestershire is the place to go for festivals. From celebrations of science to hot air balloon launches to live music and the arts, the town’s brilliant festivals and events cover a hugely eclectic array of themes. Whether you can’t wait to sample the town’s culinary delights or are looking forward to meeting up with like-minded crews, here’s what you can look forward to in this year’s social calendar. 

Food and Drink Festivals

Gear up your taste buds for comestible delicacies and refreshments, it’s all happening in Cheltenham from cider sampling and wine tasting to cheese nibbling and pie testing.

Cheltenham Craft Beer and Cider Festival


The Cheltenham Craft Beer and Cider Festival takes place in the summer . Establishing its own traditions, the festival will showcase a handpicked selection of craft beers and ciders, as well as a lots of other alcoholic and non-alcoholic options. In a family and dog-friendly setting overlooked by Leckhampton Hill, it provides a great way to kick the summer off in style and settle into holiday-mode during a luxury break in Cheltenham.   

Cheltenham Food and Drink Festival

21st – 23rd June 2023

Wine talks and drinks testing, cooking masterclasses and demonstrations, street theatre and family-friendly entertainment are all but some of the things you can look forward to during the Cheltenham Food and Drink Festival. Held annually in June, it regularly features more than 200 exhibitors from both the local and surrounding areas, as well as guest celebrity chefs. Needless to say, if you’re a foodie fan, this festival in Cheltenham is not to be missed. 

The Gin & Rum Festival 

5th August 2023

Held in Cheltenham Town Hall, the yearly Gin and Rum Festival provides spirit and liquor-lovers with a unique opportunity to sample some of the very best gins and rums around. With over 120 gins and rums, as well as extra tipples on tap, you’ll simply be spoilt for choice when it comes to dribble-worthy beverages. So, whether you’re already a gin-ius or are looking to refine your tasting skills, head on over this year and sample the fruity, the floral, the sharp and the sweet. 

Music and Arts Festivals 

Known for its literary and musical connections, Cheltenham has an unparalleled line of up arts festivals for all generations to enjoy.

Cheltenham Jazz Festival

1th - 6th May 2024

Boasting nearly 50 official concerts and welcoming 20,000 visitors, Cheltenham’s Jazz Festival has become the place to be for jazz enthusiasts, with famous attendees including Jamie Cullen, Van Morrison and Imelda May. Running across May’s spring bank holiday weekend, it ignites the town with a fusion of established and up-and-coming artists from all over the world. Watch jazz icons and local heroes take to the stage with playful tunes, complex harmonies and impressive improvisation. 

Wychwood Festival

31st - 2nd June 2024

Voted as one of the best family-friendly festivals in the UK, Wychwood Festival invites everyone from tots to grandpops to get involved in. Held at the world-famous Cheltenham racecourse each year, it incorporates all kinds of multi-generational fun, such as hundreds of music acts across four stages, stand-up comedy performances, food and drink stalls, healing gardens and more. With its cheery vibes, inclusive approach and stunning views, it’s sure to be a firm favourite. 

2000trees Festival

5th - 8th July 2023

If you’re looking for more of a sun, cider and wellies kind of festival, then look no further than 2000trees. An award-winning music festival set within rolling Cotswolds hills, this festival is all about great bands and big sounds. Alongside a number of pop-ups serving delicious food and drink, you can look forward to a line-up of musicians and groups ringing out rock and alternative-style tunes from the loudspeakers. For added incentive, the festival’s ‘thrones’ have also been shortlisted for the Best Toilets award at the UK Festival Awards. Now there’s incentive.

Cheltenham Music Festival

6th - 13th July 2024

First started in 1945, the Cheltenham Music Festival champions the best of British music. Fusing the new and the old, it is world renowned for its premieres of contemporary music, as well as its celebration of classical pieces. Taking place across 10 days, it invites music fans of all ages to follow the winding streets of Cheltenham and listen to a range of music in different locations, including grand concerts in the Town Hall and intimate performances in the Pittville Pump Room.

Cheltenham Literature Festival

6th - 15th October 2023

The world’s first literature festival, the internationally-renowned Cheltenham Literature Festival is a real highlight in the town’s calendar. Spread out across 10 days, this annual event attracts some of the greatest names in the book world, attended by award-winning novelists, poets, artists and public figures. Previous guests have included David Attenborough, Hillary Clinton, Jimmy Page, Salman Rushdie and Michael Parkinson.

Must-See Cheltenham Festivals

Along with Cheltenham’s culinary and cultural festivals are a number of other unmissable events, from big questions at Cheltenham’s Science Festival to highflyers at the town’s Balloon Fiesta.

The Cheltenham Festival and Gold Cup Day

12th - 15th March 2024

Cheltenham has long been considered the jewel in the crown of jump racing. At the centre of its racing history is Cheltenham Racecourse, set within 350 sprawling acres of countryside at the foot of the Cotswolds Hills. Though the racecourse hosts many events throughout the year, its most famous is the Cheltenham Festival, a 4-day racing event consisting of 28 races – the most important race of which is the legendary Gold Cup. 

Cheltenham Science Festival

4th – 9th June 2024

If you have a question about life, the world and the universe, it’s likely you’ll find the answer at the six-day Cheltenham Science Festival. Well, a lot of them, anyway. From the science behind taste buds to the rotation of the earth, all kinds of topics are explored. And, with some of the greatest minds and biggest thinkers taking the stage, you can look forward to intriguing and thought-provoking talks from the likes of Brian Cox, Robert Winston, Alice Roberts, Richard Dawkins and more.

Cheltenham Balloon Fiesta


A brilliant family-friendly festival in Cheltenham, the Cheltenham Balloon Fiesta will capture the minds and imaginations of all those who visit. Both providing pilots with the chance to show off their skills and onlookers the opportunity to enjoy a world-class aerial show, it sees countless balloons take to the sky for a unique multi-generational attraction. As well as hot air balloons, the festival will also put on a fireworks display, live entertainment, a funfair and lots of local food and trade stalls. 

 Feeling inspired? Take a look at our luxury cottages in Cheltenham here.

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