- Cheltenham Town FC vs Fleetwood Town – EV Charger Points Stadium – 4th October 3pm
Cheltenham will face a stiff test against Fleetwood who have had a strong start to the season. - Cheltenham Literature Festival – Montpellier Gardens – 10th – 19th October
Cheltenham Literature Festival is the world’s longest-running literature Festival, leading the way in celebrating the written and spoken word, presenting the best new voices in fiction and poetry alongside literary greats and high-profile speakers. - Blood Brothers – Everyman Theatre – 14th – 18th October
Willy Russell’s legendary musical tells the captivating and moving tale of twins separated at birth, who grow up on opposite sides of the tracks, only to meet again with tragic consequences. - FilmChelt – Cheltenham Film Festival – Various Venues – 18th – 26th October
FilmChelt, Cheltenham’s independent film festival, celebrating cinema, moving image and the art of film making, is for film lovers everywhere. This year’s country focus is Mexico. The Festival has a pre-launch concert ‘Echoes of the Oscars’ at Cheltenham Ladies College. This is a gala concert of Oscar winning and nominated film scores performed live by The film Orchestra, a 70-piece symphony orchestra. This exciting event, is a pre-launch of the new Cheltenham Film Festival. Join us to celebrate the iconic marriage of cinema with film music and the art of film making in all its forms. - Fishermens Friends – Cheltenham Town Hall – October 23rd
In celebration of performing together for over 30 years on stages across the world, Fisherman’s Friends are going on a new UK tour. Having sold out every venue on their last tour, the band look forward to performing old songs and new. - October Showcase – Cheltenham Racecourse – 24th & 25th October
The Showcase raises the curtain to the 2025/26 Cheltenham season, once again, the thundering hooves, eager participants and excited fans will return to the Home of Jump Racing. - Cheltenham Town FC vs Walsall – EV Charger Points Stadium – 25th October – 12.30pm
Cheltenham Town FC under new Manager, Steve Cotterill face a stern test against league leaders, Walsall. - The November Meeting – Cheltenham Racecourse – 14th-16th November
The magic starts here, the pace has quickened, the atmosphere is electric and exhilarating racing action will be revealing Cheltenham Festival clues. Off the track, shop till you drop in the Shopping Village, or enjoy live music across a variety of performance areas, including crowd favourite The Guinness Village. There is something for everyone at the unmissable three-day meeting which is the second biggest of the year. - 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. - A Night at the Darts – The Centaur – Cheltenham Racecourse – Friday 28th November
This year’s event includes an unforgettable event featuring an all-star lineup, including world number one Luke Humphries and Stephen Bunting along with Rob Cross, Simon Whitlock and others! It’s set to be an epic head-to-head showdown you won’t want to miss. - 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. - The Christmas Meeting – Cheltenham Racecourse – 12th and 13th December
Commence your Christmas celebrations at Cheltenham Racecourse over a weekend of top-quality racing. With the festive season about to enter the home straight, this two-day meeting is a highlight of the Christmas racing calendar and kick starts the festive sporting season.
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.