- Cheltenham Ice Rink – Imperial Gardens – 21st November – January 4th
Cheltenham’s magical covered indoor ice rink, centrally located in the beautiful Imperial Garden, is the perfect Christmas activity for all the family! Each session lasts an hour, and the real ice rink is indoors meaning that you don’t need to worry about wet weather spoiling your festive day out. - Robin Hood and His Merry Men – Everyman Theatre – 28th November – 11th January
Get ready for an all-new Christmas adventure in 2025 as the Everyman Theatre proudly presents Gloucestershire’s favourite clown, Tweedy, in Robin Hood and His Merry Men, for the first time ever! Tweedy is back in Gloucestershire’s biggest, best and most renowned pantomime, along with a cast of returning Everyman favourites in a heart-pounding thrill-ride for the entire family. - Cheltenham Town FC vs Shrewsbury Town – EV Charger Points Stadium, Whaddon Road – 26th December 3pm
The Robins will be looking to extend their recent run of good form and continue their climb up Division 2 as they welcome Shrewsbury who sit beneath them in the table. - Cheltenham Town FC vs Swindon Town – EV Charger Points Stadium, Whaddon Road – 29th December 7.45pm
The Robins welcome local rival Swindon who are right in the hunt for promotion this season. Cheltenham will not be daunted though as they recently won away at Swindon. - New Year’s Day Racing – Prestbury Park, Cheltenham Racecourse – 1st January – First Race 12.15pm
Regardless of how you celebrated New Year’s Eve, there is no better way to jump into 2026 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. - Cheltenham Town FC vs Crawley – EV Charger Points Stadium, Whaddon Road – 4th January 3pm
Cheltenham will be hopeful of picking up more points how to Crawley who sit beneath Cheltenham in the league table. - Cheltenham Town FC vs Leicester City FC – Third Round of the FA Cup – EV Charger Points Stadium, Whaddon Road – 10th January 12.15pm
Leicester City from the Championship (two leagues above Cheltenham) will present a stiff challenge in this third round FA Cup match. - In the Air Tonight – A tribute to Phil Collins and Genesis – Everyman Theatre – 15th January 7.30pm
From the epic drum breaks to the soul-stirring ballads, this show brings the sound of a generation roaring back to life. Relive the magic of Phil’s greatest moments – from his Genesis roots to his incredible solo career – in a concert that will have you singing, swaying, and dancing all night long. Starring an electrifying live band, powerhouse vocals, and a stellar cast of musicians, In The Air Tonight captures the unmistakable energy, emotion, and drive of Phil Collins like never before. - Peter Andre in the very best of Franki Valli and the Four Seasons – Everyman Theatre – 16th January – 7.30pm
The Very Best of Frankie Valli and the Four Seasons is a spectacular high-pitched celebration of timeless music from one of the biggest selling groups of all time. This nostalgic musical journey pays tribute to the life and career of those four boys from Jersey, who started singing under a streetlamp but soon went on to become one of the most recognised groups in history. From the streets of New Jersey to the dizzying heights of the West End and Broadway, this incredible music has delighted audiences for over five decades, The Very Best of Frankie Valli and the Four Seasons features all your favourite songs including Sherry, My Eyes Adored You, Big Girls Don’t Cry, Can’t Take My Eyes Off You and many more. - Festival Trials Day – Prestbury Park, Cheltenham Racecourse – 24th January – First race 12.40pm
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? - 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 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,
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