Things to do in Cheltenham | Entertainment

Between the world-famous Cheltenham Festival and the oldest-surviving theatre of the renowned architect Frank Matcham, you have all manner of incredible entertainment options in Cheltenham. Here we pick out a few of the Regency town’s top venues, which are well worth checking out to see what’s on during your stay. Who knows, you could find live music, national comedy acts, opera, masquerade balls, football matches, classic plays and seasonal pantomimes – the choice is yours.


As far as entertainment venues go, Cheltenham Town Hall is tough to beat. It’s an iconic building in the Montpellier Quarter, sitting on the corner of the Promenade and overlooking Imperial Square and the lovely flower beds of its gardens.

When it was built in the 20th century as assembly rooms, it was the place to be for the big shots of Cheltenham’s high society. Back then, it hosted masquerade balls, music recitals and all kinds of other formal events. Today, if anything, its programme is even more diverse; during your stay in Cheltenham, you could come to the town hall for music concerts, dances, balls, exhibitions, and even banquets.

Plus, on the last Wednesday of the month, the sell-out Howlers Comedy Club takes place, bringing some of the best comedy acts from the national circuit to Cheltenham Town Hall.

It doesn’t have the same levels of grandeur, but The Frog & Fiddle is just as loved by the people of Cheltenham. Since the pub opened its doors in 1998, it’s built a reputation as the best live music venue in Cheltenham and regularly hosts local artists and touring bands in The Barn, a 200-capacity gig space with bare brick walls and bags of character. The staff are friendly, and it’s a Butcombe Brewing Co. pub – so it has a great selection of drinks. Even when there aren’t any gigs on, it’s worth paying a visit to The Frog & Fiddle. Despite its prime High Street location, it boasts a big beer garden, you can play pool upstairs, and when there’s sport on, you can watch from over 14 screens spread around the pub. Best of all? It’s only a hundred metres from our Cheltenham Town Centre hotel.

Likewise, The Cotswold Inn on Portland Street is a great pub that lives and breathes live music. On Tuesdays, it hosts jam sessions, where anyone’s welcome to come down and take to the stage. What’s more, Wednesday is karaoke night, Thursday is pub quiz night, and on the weekends, it welcomes touring bands, local artists and tribute acts from every genre.

The Frog & Fiddle

The Frog & Fiddle


Cheltenham is fortunate to have four great theatre options for you to choose from. Each offers something different, but without a doubt, the most popular is the red-brick Everyman Theatre on Regent Street. It’s believed to be the oldest surviving theatre of Frank Matcham, the legendary theatrical architect who designed, constructed and refurbished over 170 theatres across the UK. He’s the man responsible for adding the Hippodrome, Hackney Empire, London Coliseum and London Palladium to the country’s capital in only a decade.

Everyman Theatre

It’s some pretty serious theatrical company, and some pretty serious theatrical companies bring their productions to Cheltenham’s most famous stage. Their programme is a diverse blend of drama, opera, ballet, dance, comedy, music and pantomime. Take a look and see what’s on during your stay.

Cheltenham’s top community theatre is the Cheltenham Playhouse, which is housed in a historic building on Bath Street. It used to be the Montpellier Baths, which were built during Cheltenham’s transformation into a luxury spa town and boasted fourteen mineral baths made from marble and Dutch tiles. Just before the end of WWII, the Montpellier Baths were converted into a theatre, and it’s been hosting excellent productions ever since. From 1960, it’s been the home of The Playhouse Company, a revered amateur community company that tackles all manner of plays from classics right the way through to contemporary writers, as well as traditional musicals.

If you’re staying at our Cheltenham Central hotel, you’ll benefit from being just a five-minute walk from The Bacon Theatre. The 566-seat theatre is owned by the Dean Close School, one of the best schools in Gloucestershire. It’s not just a venue for school productions though. The Bacon Theatre’s state-of-the-art facilities help to attract some of the best professional touring companies in the country. Year round, they run a programme of interesting theatre, live music, comedy, celebrity speakers, film and more.

Similarly, the Parabola Arts Centre is part of Cheltenham Ladies’ College, but opens its doors to the public for its excellent range of events. The stunning Grade II-listed building stands out even in the impressive Montpellier Quarter. The theatre it houses is arguably even more spectacular. It’s absolutely state-of-the-art, with a 325-seat auditorium spread across two levels and there isn’t a bad seat in the house. It’s a regular venue for Cheltenham’s various festivals, and the foyer also doubles as an art gallery.


Sporting options don’t get much more exciting than the Cheltenham Festival, which takes place at Cheltenham Racecourse every March. It’s four days of horse racing, gambling and good times, culminating in the world-famous Cheltenham Gold Cup.

If football’s your game, then make your way to Whaddon Road where Cheltenham Town F.C. play their home matches. They don’t have much to brag about in way of trophies. In fact, they’ve never played higher than the third tier of English football. Nevertheless, it’s still an entertaining day out for neutral spectators.

Looking for a hotel in Cheltenham?

Come to the Cotswolds and stay any one of our Cheltenham hotels while you explore the most complete Regency town in the UK. Whether you're planning your visit around Cheltenham's festival calendar, or you simply fancy ticking off some of the town's top attractions such as Sudeley Castle, take your pick from our three conveniently located hotels.