- Santa Express – Gloucestershire Warwickshire Steam Railway – Cheltenham Racecourse Station – November 23rd – December 23rd
Get ready for an enchanting adventure as GWSR transport you to the North Pole (Toddington Station) and back. Their beautifully restored steam train, adorned with festive decorations, sets the stage for an unforgettable experience. Includes a private meeting with Santa and an age appropriate gift for your child. Booking essential as these special trains always sell out. - A Night at the Darts – The Centaur, Cheltenham Racecourse – 27th November
Get ready for an electrifying night of darts! Watch as top professional players, including world Number 1 Luke Humphries, go head-to-head in a thrilling competition. - Cheltenham Ice Rink – Imperial Gardens – 29th November – 5th January
The return of the hugely popular covered ice rink. All skaters welcome including from the age of three and above. - Alladin – Christmas Pantomime – Everman Theatre – 29th November – 12th January
Embark on a fun-filled adventure featuring the return of Gloucestershire’s favourite dame, Kevin Brewis playing Widow Twankey, as she tries to control the comic chaos caused by her son, Tweedy Twankey! With dazzling costumes, breath-taking set designs, and iconic musical numbers, the Everyman Theatre Pantomime is an annual treat not to be missed. - Cheltenham Town FC vs Port Vale FC – EV Charger Points Stadium – Tuesday 3rd December 7.45pm
Cheltenham Town’s recent run of good form will face a stern test against League Two league leaders, Port Vale. - The Christmas Meeting – Cheltenham Racecourse – December 13th and 14th
Commence your Christmas celebrations at Cheltenham Racecourse over a weekend of top-quality racing. - Cheltenham Town FC vs Morecombe – EV Charger Points Stadium – 14th December
Cheltenham will be hoping to continue their recent climb up the table against Morecombe, who currently sit in the relegation places. - New Year’s Day Racing – Cheltenham Racecourse – 1st January
Regardless of how you celebrated New Year’s Eve, there is no better way to jump into 2025 than racing on New Year’s Day at Cheltenham. Thrilling and high-quality racing action, that is sure to provide Cheltenham Festival insight, fresh air, and amazing free family entertainment. There are seven highly-competitive races on the day with Graded and Listed contests, the racing action will blow away those New Year’s Eve cobwebs. - Chicago The Musical – Everyman Theatre – 20th – 25th January
Chicago, the “sexiest musical ever” (Metro) comes to Cheltenham in January for one week only starring Coronation Street’s Faye Brookes (Dancing On Ice, Grease, Legally Blonde) as Roxie Hart, West End and TV stars Brenda Edwards (Loose Women, Chicago, The X Factor) as Matron ‘Mama’ Morton and Kevin Clifton (Strictly Come Dancing, Everybody’s Talking About Jamie) as Billy Flynn. “Murder, greed, corruption, exploitation, adultery and treachery…all those things we hold near and dear to our hearts” So begins the international multi-award-winning musical, Chicago. Set amidst the razzle-dazzle decadence of the 1920s, Chicago is the story of Roxie Hart, a housewife and nightclub dancer who murders her on-the-side lover after he threatens to walk out on her. - Festival Trials Day – Cheltenham Racecourse – 25th January
This is the final opportunity to see the sports protagonists go out to battle on Cheltenham Racecourse’s hallowed turf before the Cheltenham Festival. What horses will catch the eye before those four days of extraordinary in March, will we see returning champions defending their crown? Whilst anything can happen in March, Festival Trials day maybe able to give us a clearer picture. - Cheltenham Festival – Cheltenham Racecourse – 11th – 14th March
Cheltenham Festival 2025 is the pinnacle event of the jump-racing calendar. Guaranteed excellence, whether you join on Champion Day on Tuesday, Style Wednesday, St Patrick’s Day on Thursday or Gold Cup Day on Friday. - Cheltenham Jazz Festival – Montpellier Gardens – 30th April – 5th May
The Cheltenham Jazz Festival 2025 is one of the cultural highlights of the year. Big names already announced include the likes of David Gray, Corinne Bailey-Rae, Amadou & Mariam, Nubya Garcia and Jools Holland. Full programme to be announced in early 2025.
Visiting one of these events? Get in touch to speak to one of our friendly team members to discuss our short term rentals in Cheltenham.