- Cheltenham Town FC vs Barrow – The EV Charger Points Stadium, Whaddon Road – Friday 6th March 7.45pm
Cheltenham will be hoping to continue a recent run of improved results that has seen them remain undefeated in four matches against Barrow who are below Cheltenham in the table. - Cheltenham Festival – Prestbury Park, Cheltenham Racecourse – 10th – 13th March
The pinnacle event of the jump-racing calendar. The Cheltenham Festival is an experience like no other, where every moment pulses with energy and excitement. - Cheltenham Town FC vs Crewe Alexandra – The EV Charger Points Stadium, Whaddon Road – Tuesday 19th 7.45pm
Steve Cotterill’s Cheltenham Town face a tough challenge at home against promotion chasing Crewe Alexandra. - The Spy who came in from the Cold – Everyman Theatre – 14th – 18th April
For the first time ever, a novel by John le Carré — the undisputed master of the modern spy genre whose works include Tinker, Tailor, Soldier, Spy and The Night Manager — is brought to life in a thrilling stage adaptation. Starring Ralf Little (The Royle Family, Death In Paradise), The Spy Who Came In From The Cold is a riveting journey through the fog-shrouded terrain of Cold War espionage, deception, and moral compromise. Following a sold-out run at Chichester Festival Theatre and direct from the West End, this gripping new play written by David Eldridge (Beginning, Middle, End) and directed by Jeremy Herrin (Grace Pervades, People, Places & Things) comes to Cheltenham for 1 week only. - For the love of Rugby – Cheltenham Town Hall – 19th April
Do you love rugby? Ben Youngs and Dan Cole do, and no men have played for England more times than them.
Newly retired, they’re taking their podcast to the stage, bringing you the best stories from across their careers. You can expect all the bits they’re too afraid to say in episodes, games, surprises and potentially a quiz. Why? For the love of the game. - Cheltenham Jazz Festival – Various Town Centre venues – 29th April – 4th May
One of the highlights of the Cheltenham Calendar, this Festival attracts some of the biggest stars of the Jazz world. - Cotswold Festival of Steam – GWSR, Cheltenham Racecourse – 23rd – 25th May
Board one of their Steam trains at Cheltenham Racecourse Railway Station and visit their stations at Toddington and Broadway, where there will be a variety of displays and stalls. - Wychwood Festival – Cheltenham Racecourse – 29th – 31st May
The line up for this fantastic family friendly Festival includes Craig David, The Kaiser Chiefs, Sophie Ellis Bextor, the Levellers and Feeder. - Cheltenham Food and Drink Festival – Montpellier Gardens – 19th, 20th and 21st June
Over the last 17 years this Festival has featured some of the best chefs and wine experts within the UK. The event also features some of the most talented local chefs to be found in the Cotswolds. Three days of fabulous free talks – from chef insights to wine experiences. Don’t miss the exclusive cheese & wine masterclasses with the best in the business. Artisan food makers stalls, a great selection of bars and food from all round the world. - Cheltenham Music Festival – Various Town Centre venues – 3rd – 11th July
Since 1945, Cheltenham Music Festival has been a home for extraordinary music. Its 80th year in 2025 was a landmark season of celebration, and in 2026 the Festival looks ahead – championing world-class classical music performers and bold new voices in Cheltenham’s most beautiful spaces.
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.