- Roald Dahl’s Charlie and the Chocolate Factory – Everyman Theatre – 15th – 19th April
A performance by Cheltenham Operatic and Dramatic Society. Escape into a world of pure imagination this Easter with this devilishly delicious story of young Charlie Bucket. Based on the iconic story from Roald Dahl, join Charlie and Grandpa Joe as they enter the iconic world of Willy Wonka and his incredible chocolate factory. - The April Meeting – Cheltenham Racecourse – 16th and 17th April
The April Meeting is a wonderful two-day meeting at the Home of Jump Racing. The Spring sunshine shining over the famous Cleeve Hill and hallowed Cheltenham turf is sure to put a spring in your step and provide a brilliant day out with high-quality racing. Throughout the two-day meeting, there will be live music from The Quevegas Stage, the perfect place for refreshments and entertainment between races. - Cheltenham Town FC vs Gillingham FC – EV Charger Points Stadium – 18th April 3pm
Bank Holiday Friday football action at Cheltenham Town take on Gillingham who are placed just below them in the league. - Cheltenham Town FC vs Carlisle United – EV Charger Points Stadium – 26th April 3pm
As the season draws to a close a win in this match against Carlisle could condemn them to relegation out of the Football League. - 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. - Race Night – Cheltenham Racecourse – 2nd May
The curtain comes down on the 2024/25 season with Cheltenham’s only evening fixture. The evening promises a fun vibe from start to finish. Local legends The Chip Shop Boys perform in a spectacular post racing finale, where they’ll bringing the season to a close with an extended live performance. This is a meeting that allows amateur riders and trainers to compete for the ultimate dream of winning at the Home of Jump racing with seven fiercely fought Hunter chases. - Cotswold Festival of Steam – GWSR Cheltenham Racecourse Station – 24th-26th May
Get ready to embark on a journey through time, where the past comes alive and the heritage of steam locomotives is celebrated in all its glory. Join us for a long bank holiday weekend filled with the magic of steam, picturesque landscapes, and the rich history of the Cotswolds. The Cotswold Festival of Steam Gala is a spectacular event that brings together railway enthusiasts, families, and adventure seekers. Held amidst the charming Cotswold countryside, this gala showcases the elegance and power of steam locomotives, offering a unique experience for visitors of all ages. - Wychwood Festival – Cheltenham Racecourse – 30th May – 1st June
Wychwood, the unmissable family-friendly festival, returns in 2025. 3 days of Music, Comedy plus 100s of workshops and activities for all ages. Acts already announced include – Shed Seven, James, Doves, The Zutons, Daniel Bedingfield and Fisherman’s Friends. - Cheltenham Science Festival – Imperial Gardens and various venues around the town – 3rd – 8th June
Asking the most important questions about the world today, Cheltenham Science Festival hosts six days of spectacular science. Bringing together the UK’s most respected scientists, favourite science communicators, writers, and artists to talk about today’s hottest topics. - Cheltenham Food & Drink Festival – Montpellier Gardens – 20th – 22nd June
Cookery demonstrations, wine and cheese tastings. Artisan food producer stalls, fresh cuisine from a wide array of countries. Live music and entertainment. - Cheltenham Cricket Festival – Cheltenham College Cricket Pitch – Various dates 17th July and 5th August
Cheltenham Cricket Festival is believed to be the longest running cricket festival in the world and takes place in the iconic setting of Cheltenham College Cricket Pitch. The Festival programme includes a double header of both the men and womens’ county teams playing Sussex Sharks in the Vitality Blast. In the same tournament there is also a womens’ match versus Middlesex. There are County Championship matches against Lancashire and Middlesex and a One Day Cup match versus Derbyshire Falcons.
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.