Explore Cheltenham: Festivals, Racing and Cotswolds Charm

In the heart of the charming Cotswolds, Cheltenham is well-known for its lively festival season.

Kicking off in spring at Cheltenham Racecourse with the main event in the jump-racing calendar, Cheltenham’s festivals of music, science, literature and food and drink unfold through summer and autumn. Beyond festivals, Cheltenham is a stunning town worth exploring in its own right.

Get ready to explore Cheltenham’s stunning scenery, buzzing festivals and vibrant cultural scene. 

Cheltenham Racecourse

Cheltenham FestivalCheltenham Racecourse has been offering the ultimate horse racing experience since 1815, with the main event taking place each spring at the Cheltenham Festival. The hallowed Cheltenham turf goes on to host high-quality racing all season long. Over the coming months, there are plenty of races to see alongside a programme of music and other sporting events.

And there’s much more to a visit to Cheltenham than racing. Dress in your best, visit the shopping village and wine and dine at one of the many restaurants or bars.

Cheltenham Jazz Festival

1st-6th May 2024

This annual event runs in the first week of May and brings 20,000 jazz lovers together to celebrate the genre. The heart of Cheltenham is transformed into a Festival Village with a free stage showcasing stars of the future and local schools. Other stages include the main Arena, hosting jazz icons and emerging talent, and the intimate Parabola Arts Centre.

Big names performing in 2024 include Dionne Warwick, Jack Savoretti, Morcheeba, Ladysmith Black Mambazo, UB40 and Gregory Porter. Plus, don’t forget the Brand New Heavies performing with the London Concert Orchestra!

Cheltenham Literature Festival

4th-13th October 2024

When the music stages come down for the autumn, a season of literature festivals begins in Cheltenham. New voices in fiction and poetry star alongside literary greats and high-profile speakers in a 10-day festival celebrating the written and spoken word.

Montpellier Gardens is transformed into a booklover’s haven with something for readers of all genres. There’s plenty for families too, with authors and illustrators of all your favourite bedtime stories popping in. The line-up for 2024 will be announced over the summer but expect a packed programme of huge names and rising stars.

Cheltenham Food and Drink Festival

21st-23rd June 2024

Food and drink festivalRing in the summer with good company, great food and fine wine. Cheltenham Food and Drink Festival combines it all across three days in Montpellier Gardens. The most talented chefs from the Cotswolds come together with knowledgeable food and wine experts from across the UK.

The lineup is crammed with demonstrations, tastings, talks and masterclasses. A programme of live music, street theatre and children’s entertainment also takes place over the weekend – don’t miss the dog show, the annual Cotswold BBQ Championships and gardening events if you’re keen to grow your own!

Wychwood Festival

31st May-2nd June 2024

Wychwood FestivalGiddy-up to the groove! Sister Sledge, Texas and Ocean Colour Scene are set to headline Cheltenham’s electric music festival. Held at Cheltenham Racecourse, this vibrant music festival is also set to host The Coral, Corrine Bailey Rae, Peter Hook & The Light plus many more across various stages.

Stand-ups, including Marcus Brigstocke and Andrew Bird, lead a programme of comedy, plus there are tonnes of family entertainment, activities and workshops.

Stay nearby

Completely-Suzuki Stadium, Whaddon Road

Completely Suzuki StadiumHome to Cheltenham Town Football Club since 1932, Whaddon Road, also known as Completely-Suzuki Stadium, is a must-visit for football fans. This famous stadium is home to history, passion and community spirit combined in an infectious atmosphere.

Whether you’re a die-hard football fan or just in it for the experience, visit on match days alongside seasoned fans for the full experience. Food and drink outlets are available in all sections of the ground, so you can easily get your hands on a traditional pie and pint. Don’t forget to stop by the club shop to pick up your merch and represent Cheltenham Town once you head home.

Everyman Theatre

Everyman Theatre, CheltenhamDating back to 1891, this ornate Frank Matcham-designed theatre offers a diverse range of world-class and community-centred theatre shows. Its programme of performances includes plays, musicals, comedy and dance throughout the main Edwardian-style auditorium and smaller performance spaces. Matcham’s Restaurant serves up pre-show meals, while the Cafe Bar offers a relaxed space to dine and enjoy drinks.

In the coming months, you can catch everything from Julian Clary to The Addams Family musical, and classic performances from the English Touring Opera and Birmingham Royal Ballet.

Cheltenham Fringe Festival

20th-26th May 2024

Playhouse CheltenhamA community theatre and cinema housed in the former Montpellier Baths, the Playhouse offers a broad range of film, theatre, music and comedy year-round. Between the 20th and 26th May, the Playhouse plays host to the Cheltenham Fringe Festival. Get ready for poetry readings, talks, storytelling sessions, laugh-out-loud comedy, workshops and family fun – all led by emerging and established talent!

Among them, The Other Theatre Company presents This Is Not Medea – a one-woman black comedy show about passports, pints, a global pandemic and murder. How Darling, meanwhile, is a one-drag-queen show featuring a mix of live singing, lip-syncs and drag-burlesque.

The Bacon Theatre

bacon-theatre-cheltenhamAs Cheltenham’s most unique theatre, The Bacon Theatre offers film, live music and dance from outstanding local and touring acts.A children’s ballet performance of Goldilocks and Star Wars in Concert are just some of the upcoming performances!

Each August, the Tuckwell Open-Air Theatre Festival runs alongside The Bacon Theatre’s program. The stone-built amphitheatre is embraced by lush trees and shrubs, creating an idyllic setting, perfect for losing yourself in the drama, pulsating to sublime jazz or enjoying colourful family entertainment – all under the open sky. You don’t want to miss the enchanting Cinema Under the Stars.

Leckhampton Hill

Leckhampton HillNo visit to Cheltenham is complete without taking in the stunning Cotswold countryside. Leckhampton Hill offers the perfect accessible viewing spot – suitable for families, wheelchairs, bikes and walkers. The hill lies within the Cotswolds Area of Outstanding Natural Beauty and is a Site of Special Scientific Interest, due to the limestone grassland that grows there.

A 3km walk up the hill offers a great display of wildflowers in season. Plus, you’ll spot a wealth of wildlife, including small mammals, reptiles, butterflies, buzzards and kestrels.

The Wilson Art Gallery and Museum

The Wilson Art GalleryGloucestershire’s premier gallery and museum is home to an internationally significant art collection and regularly changing displays. Explore the Arts and Crafts Movement alongside fine art from many movements and centuries. You can also dive into the Open Archive dedicated to Antarctic voyager Edward A. Wilson.

The Wilson Art Galleries include the Sir Charles Irving Community Art Gallery, Summerfield Exhibition Gallery and a brand new World of Wonders children’s gallery. Running until September, the current exhibition tells an extraordinary story of 20th-century art and modern love. The exhibit also features work by iconic artists including Vanessa Bell, Duncan Grant, Picasso and Modigliani.