Things to do in Cheltenham- Page 5

Victorian Book Group: Rites of Passage by Judith Flanders

Welcome to the book group with a historic twist! Revisit old favourites and discover forgotten classics in this monthly meet-up.

Holst Victorian House, Cheltenham

Yacht Rock Live

The smoothest sounds ever to sail the seven seas.Yacht Rock: Live is a lush, feel-good celebration of the golden era of smooth West Coast pop, soft rock and sop…

Everyman Theatre, Cheltenham

Prescott Hill Climb Simulator Experience

Join our team of experts for a Prescott Hill Simulator Experience Session! The day is split into either a morning or afternoon session.

Prescott Hill Climb, Cheltenham

New

Hotel California

Hotel California, a six piece ensemble of musicians will perform their spectacular new critically acclaimed show that gives you a concert experience of 100 minu…

Cheltenham Town Hall, Cheltenham

Howlers

Welcome to Howlers at the Playhouse, the home of great comedy in Cheltenham! Every month at Howlers, we bring you the very best in stand-up with top notch line-…

Cheltenham Playhouse, Cheltenham

The Bowie Band

The Bowie Band performs favourite songs from David Bowie, celebrating his legacy and live experience.The Bowie Band, featuring incredible musicians from The Alb…

Cheltenham Playhouse, Cheltenham

Jive Talkin'

Renowned as the original and very best Bee Gees tribute show — and the only one to have actually performed with the original Bee Gees!

Cheltenham Town Hall, Cheltenham

British and Midland Hill Climb Championships - The Closing Meeting

The British Hill Climb Championship join us for the closing round of the 2026 season, with practice on Saturday and timed runs and Run Offs on Sunday.

Prescott Hill Climb, Cheltenham

The Holst Birthday Concert

A programme of songs by Gustav Holst and Ralph Vaughan Williams performed by Gareth Brynmor John (baritone) and William Vann (piano)Gareth Brynmor John is an es…

All Saints' Church, Cheltenham

A Trick Down Memory Lane

A Trick Down Memory Lane” pushes the boundaries of magic in a way you’ve never seen before. Through storytelling, edgy magic, and dry humour, Charlie revisits s…

Cheltenham Playhouse, Cheltenham

Suzannah Lipscombe & Kate Williams: To Kill A Queen

Suzannah Lipscomb & Kate Williams — To Kill a Queen: Elizabeth I, Mary, Queen of Scots, and the Politics of SurvivalTwo queens. One crown.

Cheltenham Town Hall, Cheltenham

Candle Making and Cake with Time to Burn Candles

Treat yourself to the perfect end-of-Summer "gift for me" at Elkstone Tipi.Candle Making in the Tipi is such a unique event and doing it with friends is even be…

Elkstone Studios, Cheltenham

Murder on the Cheltenham Fryer

There's been a murder! Join us for an evening of Fish & Chips in the Cotswolds, but can you work out 'whodunnit?!'

Toddington Station, Cheltenham

New

Autumn Railwayana Car Boot

Whether you’re a serious collector, a casual enthusiast, or simply curious about the world of railway memorabilia, this is the perfect opportunity to browse, bu…

Toddington Station, Cheltenham

New

An Audience with Nigel Mansell

The ultimate evening with Nigel Mansell, full of entertainment and will give you a full insight into his career.Nigel Mansell started racing in British Formula…

Cheltenham Town Hall, Cheltenham

The Mousetrap

Solve theatre's most famous mysterySince 1952, Agatha Christie’s The Mousetrap has captivated the world with silent clues, shifting shadows and the best-kept se…

Everyman Theatre, Cheltenham

Love Hurts

Live & louder than ever!Back for its third year of rocking the UK, Love Hurts returns with the heartbreak soundtrack of a generation!

Cheltenham Town Hall, Cheltenham

Smokey Joe's Jazz Club with special guest Olivia Cuttill

It's always a great night at Smokey Joe's Jazz Club hosted by the jazz club team (Alex Steele, Mike Green, Kim Cypher and Mike Cypher) at one of Cheltenham's co…

Smokey Joe's, Cheltenham

Boss Cass - September UK Tour!

This September 25th Join us as we welcome the UK's favourite One Man Punk MACHINE 'BOSS CASS' Back to the barn for his LONG awaited return!

The Frog & Fiddle, Cheltenham

New

Model Railway Weekend

A brand-new event celebrating the best of the model railway world across multiple locations on our heritage line.

Toddington Station, Cheltenham

New

The FM Songbook - The Ultimate Tribute To Fleetwood Mac

Earning rave reviews wherever they play and ranked in the 'Top 20 Tribute Artists & Bands in the UK' by Champions UK plc Entertainment Agency, six piece tribute…

The Bacon Theatre, Cheltenham

The FM Songbook – The Ultimate Tribute to Fleetwood Mac

"Witnessing The FM Songbook live in action, is like capturing a little sprinkling of stardust".Kelly Scanlon, Far Out MagazineEarning rave reviews wherever they…

The Bacon Theatre, Cheltenham

New

Vintage Long Course

The VSCC return to Prescott for their Long Course championships, taking in the famous Ettores Bend.

Prescott Hill Climb, Cheltenham

Model Railway Weekend

A brand-new event celebrating the best of the model railway world across multiple locations on our heritage line.

Cheltenham Racecourse Station, Cheltenham

New

Wood-Fire & Vine Feast Lunch

This summer, celebrate the spirit of Sicily with a new open-air dining experience, Wood, Fire & Vine.A set menu that brings together bold Mediterranean flavours…

Hotel du Vin, Cheltenham

New

Cheltenham XL Comedy Club featuring: Milton Jones

Get ready for an unforgettable night of live comedy at Everyman Theatre, Cheltenham with a huge bill led by one of the UK’s most brilliantly surreal stand-ups.M…

Everyman Theatre, Cheltenham

Present Laughter

Tracy-Ann Oberman stars as Geri Essendine in this new production of Noel Coward’s celebrated and hilarious portrayal of the temptations and pitfalls of theatric…

Everyman Theatre, Cheltenham

Opera Boys - Starring Paul Potts

The powerhouse classical - crossover sensation The Opera Boys are thrilled to announce their final tour, featuring the world - renowned tenor and very first win…

Cheltenham Town Hall, Cheltenham

English Symphony Orchestra: Portraits and Landscapes

Our season opens with a vibrant evening of evocative works celebrating humanity's deep spiritual connection to the natural world.

Cheltenham Town Hall, Cheltenham

Oktoberfest at Dunkertons

Let's get this Oomparty started.Dust off your lederhosen, fill your steins and warm up those vocal cords, because The Oomparty Band are here to bring you the ul…

Dunkertons, Cheltenham

New

Silver Footplate Experience

A Footplate Experience course makes a brilliant Christmas, birthday or anniversary gift!

Toddington Station, Cheltenham

New

Toast on Tour 2026! - Full Line-Up Tba

TOAST are a genre-blending punk band that ooze charisma. Sweaty, aggressive, and clear in vision as well as message.

The Frog & Fiddle, Cheltenham

Devils Aquathlon & Swim Challenge In Association with Cobalt

The Ultimate Swim Run, THE DEVIL'S AQUATHLON is backSet yourself a goal this summer and complete the Cheltenham Lido Devils Aquathlon.

Cheltenham Lido, Cheltenham

Motown Night

Includes a 3 course meal and live entertainment with Mark Walby.

Leonardo Hotel, Cheltenham

Metropolitan Opera: Così fan tutte

The Met: Live in HD season continues with Mozarts satirical comedy of fickle young love.

Cineworld Cheltenham, Cheltenham

Season Finale

The season ending meeting for BOC and Invited Championships

Prescott Hill Climb, Cheltenham

Mc Devvo - 20th Anniversary Tour

ALRIGHT YOUNS! The Donny Soldier 'MC Devvo' is back once again for his 20th Anniversary tour!

The Frog & Fiddle, Cheltenham

Rodgers & Hammerstein

The Fulltone Symphony Orchestra & ChorusConducted by Anthony Brown

Cheltenham Ladies' College, Cheltenham

Gary Branch Upstairs Downstairs Concert

On Sunday 4 October, we have two very special recitals at 15:00 and 18:00. In both recitals, Gary Branch will be playing Holst's Collard & Collard piano (on whi…

Holst Victorian House, Cheltenham

Annie

The smash-hit West End production of ANNIE, the world’s favourite family musical, comes to Cheltenham for 1 week only.Set in 1930s New York, brave young Annie i…

Everyman Theatre, Cheltenham

ShakeItUp Shakespeare

Shakespeare hasn’t written anything new for an Age, so we thought we would give him a hand…Using his language, your audience suggestions and our overactive imag…

Cheltenham Playhouse, Cheltenham

Mixed Traction Extravaganza

An action packed weekend of mixed traffic locomotives operating an intensive timetable!

Cheltenham Racecourse Station, Cheltenham

New

Mixed Traction Extravaganza

An action packed weekend of mixed traffic locomotives operating an intensive timetable!

Toddington Station, Cheltenham

New

Dee & Griffin Dog Swim

Come and enjoy the glory and ambience of the lido with your four legged friends. Swim, smile and soak up the natural beauty and energy the lido and a family’s b…

Cheltenham Lido, Cheltenham

Save the date

Save the Date: Northern Lights & Russian SightsThis concert brings together brilliance, lyricism, and sweeping romantic power in a richly contrasted programme.

Pittville Pump Room, Cheltenham

Northern Lights & Russian Sights

This concert brings together brilliance, lyricism, and sweeping romantic power in a richly contrasted programme.

Pittville Pump Room, Cheltenham

Finlay Christie: Champagne Casanova

Finlay Christie (Live at the Apollo, 8 out of 10 Cats Does Countdown, Have I Got News For You) humblebrags for an hour about his fuckboy era and his new search…

Cheltenham Playhouse, Cheltenham

Victorian Book Group: In A Glass Darkly by Sheridan Le Fanu

Welcome to the book group with a historic twist! Revisit old favourites and discover forgotten classics in this monthly meet-up.

Holst Victorian House, Cheltenham