24 reasons to head to Cheltenham in 2024

With awe-inspiring events, fabulous festivals, historic milestones and famous faces all set to grace Cheltenham this calendar year, 2024 is looking set to be a monumental time for The Festival Town.   

Witness the grand celebration of the 100th anniversary of the spectacular Gold Cup, laugh your socks off at one of the many high-profile comedy gigs coming to the Town Hall, celebrate the 75th anniversary of the world's longest-running Literature Festival, and feast to your heart's content at one of the many new eateries getting ready to open their doors this year.

Read on below for 24 more reasons you'll want to visit Cheltenham in 2024...

1. Cheltenham Observation Wheel 

Imperial Gardens, 9th February – 3rd March 

The Cheltenham Observation Wheel is returning to Imperial Gardens for three weeks in February and the beginning of March. This is your chance to enjoy bird’s-eye views over Regency Cheltenham with exciting free family entertainment planned to celebrate it's return over the weekends. 

2. The Cheltenham Festival and Gold Cup

Cheltenham Racecourse, 12th – 15th March, 100th anniversary of the Gold Cup – 16th March 

Attend the Cheltenham Festival and become a part of history, celebrating the monumental 100th anniversary of Gold Cup Day. Four breath taking days, 28 races at stake, unrelenting prestige, competition, and excitement. 

3. Cheltenham Science Festival 

Imperial Gardens & various locations around Cheltenham, 4th – 9th June 

Explore the important questions shaping the world today, Cheltenham Science Festival, where six days of captivating science unfold in Imperial Gardens. Bringing together the UK’s most respected scientists, favourite science communicators, writers, and artists to talk about today’s hottest topics. 

4. Cheltenham Literature Festival 

Montpellier Gardens, 3 - 13 October

The impressive ten-day programme includes the world’s foremost writers, thinkers and performers whilst celebrating its 75th year anniversary as the longest running Literature Festival of its kind in the world. 

Theatre and Entertainment

Embark on a visit to Cheltenham and discover a town that exudes endless entertainment for everyone to enjoy, filled with vibrant theatre productions, top-notch comedy and mesmerising music events. 

5. Everyman Theatre

Regent Street, Cheltenham, GL50 1HQ 

Everyman Theatre boasts an impressive events calendar, featuring a nearly daily line up of productions, including many West End classics. The upcoming shows showcase a diverse range, with highlights such as Shrek the Musical, Bonnie & Clyde, Life of Pi, and the return of the Ukrainian National Opera after a stunning Cheltenham debut last year.

6. Cheltenham Playhouse Theatre 

47-53 Bath Rd, Cheltenham GL53 7HG 

Cheltenham Playhouse presents a variety of captivating events, spanning genres like musicals, theatre, comedy, and more, making it a must visit venue. Enjoy the musical talent of Joao Menezes Trio, up and coming comic talent at the monthly Howler's Comedy Club, and a brand-new musical theatre review celebrating 130 years of the Cheltenham Operatic Dramatic Society. 

7. Dunkertons Cider 

Dowdeswell Park, London Road, Charlton Kings, GL52 6UT 

Dunkertons Cider features regular entertainment and activities for all to enjoy, such as live music, Saturday Cinema Club, dance classes for pre-schoolers, quiz and comedy nights, crafts and wellbeing sessions and the fantastic Retrospective of House events. New for 2024 are an exciting assembly of jazz sessions, taking place on the first Thursday of the month from March. 

8. Cheltenham Town Hall, Pittville Pump Room and The Wilson Art Gallery & Museum

From music and comedy to exhibitions, dance, and family events, these unique venues provide a diverse array of experiences for the community and beyond. Huge comedy acts coming to the Town Hall this year include Rhod Gilbert, Rosie Jones and Jack Dee, amongst many others. While one of the most impressive private collections of 20th-century art in England, The Radev Collection, will bring world-class modernist paintings from the likes of Pablo Picasso, Amedeo Modigliani and Vanessa Bell to the Wilson from 8 March.

Live music events

Cheltenham takes great pride in being the host of a diverse array of annual music festivals and events.

9. Cheltenham Jazz Festival

Montpellier Gardens, 1st - 6th May 

The festival celebrates a multitude of jazz genres featuring a carefully curated blend of international jazz icons, emerging talents, and unique festival performances ensuring a programme that caters to every music enthusiast. First release artists for this year include Jack Savoretti, Dee Dee Bridgewater and UB40.

10. Wychwood Festival 

Cheltenham Racecourse, 31st May – 2nd June 

Over the weekend, you can expect to be entertained with more than 100 acts across indie, world and folk genres, and across four stages. Add to that comedy, over 100 workshops for all ages, great food and Wychwood Ales, healing gardens, the artists quarter plus idyllic camping beneath the Prestbury Hills. The fabulous line up has just been announced with tickets selling quickly. 

11. Cheltenham Music Festival

Various venues around Cheltenham, 6th – 13th July 

Attend one of the UK’s leading classical music festivals, bringing together eight days of live music in the Regency spa town of Cheltenham. The festival prides itself on encouraging a spirit of curiosity and welcoming bold performances. 

12. 2000 Trees Festival

Upcote Farm, Withington, 10th – 13th July

A multi-day extravaganza set in the stunning Cotswold Hills, just outside Cheltenham. You’ll get three nights camping, a friendly, intimate atmosphere plus amazing food and locally produced ciders, ales & lagers. Headliners this year include The Gaslight Anthem and Manchester Orchestra.

Arts and History

Immerse yourself in the fascinating blend of incredible art and intriguing history that Cheltenham offers, featuring everything from captivating locomotives to beautifully painted buildings scattered throughout the town.

13. Craft Festival Cheltenham 

Cheltenham Town Hall, 8th – 10th March

Bringing a hundred of the finest designer makers from across the UK exhibiting and the chance to buy directly from designer makers of jewellery, ceramics, furniture, textile artists, glass and many more. 

14. Cheltenham Poetry Festival 

Various venues throughout Cheltenham, 19th – 29th April  

The festival offers events featuring the greatest living poets, spoken word artists, musicians, actors, dancers, writers and film makers. The festival also offers an extensive outreach programme for those who suffer economic, physical and other barriers to cultural inclusion.

15. Fresh: Art Fair

The Centaur, Cheltenham Racecourse, 26 – 28th April

The Art Fair will host 50 leading galleries showing 5,000 prints and paintings, sculpture, glass and ceramics by 500 UK and international artists. 

16. Cotswold Festival of Steam

Gloucestershire Warwickshire Steam Railway, 25th – 27th May

A spectacular event that brings together railway enthusiasts, families, and adventure seekers. Held amidst the charming Cotswold countryside, the gala showcases the elegance and power of steam locomotives, offering a unique experience for visitors of all ages. 

17. Cheltenham Paint Festival

Various locations around Cheltenham, 27th – 28th July 

Cheltenham Paint Festival is returning to Cheltenham for its sixth year and can be enjoyed year-round. All the large scale and full wall street art murals are permanent and therefore available to appreciate long after the artists have left town.

18. Holst Victorian House

4 Clarence Road, Pittville, GL52 2AY

Composer Gustav Holst’s life and times can be discovered at Cheltenham's Holst Victorian House, a time capsule of 19th-century life and creativity. This year, their passionate community will be at the heart of a milestone anniversary celebration, marking 150 years since the famous composer's birth.

Sporting events and activities

Whether you're a spectator or an active participant, Cheltenham offers plenty of sporting events and activities that are sure to get your adrenaline pumping

19. Cheltenham's Three Peaks Challenge 

Crickley, Leckhampton and Cleeve Hill, 8th June 

Take part in an exhausting but exhilarating adventure tackling the three tallest peaks in the county: Crickley, Leckhampton and Cleeve Hill, whilst raising vital funds for a fabulous local charity.  

20. Cheltenham Running Festival 

Cheltenham Racecourse, 16th June 

A unique opportunity to run a chip timed 5k, 10k or Half Marathon around Cheltenham Racecourse. 

21. Cheltenham Cricket Festival 

Cheltenham College, 30th June – 19th July 

A highlight of the summer and an unmissable opportunity for any cricket fan to experience the longest running cricket festival in the world. 

22. Cheltenham 7s Festival 

Newlands Park, Southam Lane, 19th – 20th July 

Cheltenham’s only sports and music festival. This is a festival for all sport lovers, whatever your ability, age or choice of sport. 

23. Run Cheltenham 

Cheltenham Racecourse, 1st September 

Run Cheltenham offers three incredible and unique racing experiences for all ages and abilities, the event organisers have something for all running enthusiasts alike. 

24. Brand new bars and restaurants in Cheltenham 2024

Cheltenham looks set to bolster it's reputation as a world-class wine and dine destination even further this year with several recently opened and soon-to-come additions to the town's thriving food and drink sector. Check out a few of our highlights below.

Rosa's Thai

Joining the likes of Giggling Squid, Bangkok Thai and Thai Emerald this year will be Rosa's Thai. An expanding Thai chain restaurant whose menu will include authentic dishes such as Tom yum noodle soup, pad Thai, red duck pineapple curry and Rosa’s ‘khao pad’ fried rice. Although there is not yet an opening date, the eaterie has begun renovations on its Promenade site. 

Airs and Graces

Dodo Pub Co, owner of Cheltenham's The Bottle of Sauce, is set to open a second venue in the town this March, taking over the historic Grade II-listed Sudeley Arms pub on Prestbury Road. The revamp will feature Dodo Pub Co's signature style with a unique menu of Neapolitan-style pizzas and topped garlic bread.

Beet Juice Bar & Kitchen

On a mission to challenge and redefine what lunch 'on the go' can be, promising nourishment at your convenience, with healthy food options including freshly pressed juices, elevated seasonal salads and winter stews. Beet Juice Bar & Kitchen will open on Cheltenham's Regent Street later this year. 

Mr Cambrays Curiosity

Having opened just in time for Christmas 2023, Mr Cambray's is Cheltenham's newest day-to-night venue. Offering a chilled space for coffee in the day, and 7 rooms of immersive wonder to sip cocktails in at night. Located on Cambrays Place opposite Tailor's Eating House.  

Mandarin Gastro Pub

Launched in October 2023, The Mandarin Gastro Pub is Cheltenham Racecourse's first walk-in restaurant (Non-Festival Racedays). Taking inspiration from a traditional country stable, The Mandarin offers a glorious and cosy Cotswold pub feel, complete with delicious seasonal pub favourites.

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With all of these reasons to head to Cheltenham this year, you'll no doubt want to book a stay! Check out our guides to help plan your stay.