Collage of Cheltenham festivals and events

Live Performances in Cheltenham

Highlights

Cheltenham Music Festival

Cheltenham Music Festival

Cheltenham Music Festival returns for its 80th birthday celebrations, 4 - 18 July 2025, for eight…

Crowds at Cheltenham Jazz Festival 2024.

Cheltenham Jazz Festival

Cheltenham, The Festival Town, is home to one of the country’s best-loved jazz festivals,…

People stood next to big JAZZ sign.

Cheltenham Jazz Festival... around town free gigs

Keep Wednesday 30 April to Monday 5 May 2025 clear in your calendar to enjoy six days of free…

Cheltenham Literature Festival

Cheltenham Literature Festival

Cheltenham Literature Festival, 10-19 October, promises a feast for the mind. As the world’s…

Number of results:

Number of results: 87

, currently showing 41 to 60.

  1. Add CFF25: Gloucester Comedy Carful to your Itinerary

    CFF25: Gloucester Comedy Carful

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    29 May 2025Open 18:30 -

    Four middle-aged, working class, white men return to the scene of the crime...last year.

  2. Add CFF25: Writer's Block to your Itinerary

    CFF25: Writer's Block

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    29 May 2025Open 18:00 -
    From:
    30 May 2025Open 18:00 -
    From:
    31 May 2025Open 18:00 -

    Two older, cynical performers work on possible formats for their new humorous show. This play highlights the creative writing process in going from 'page to stage'.

  3. Add CFF25: Budgens & Dragons: There's a Scratch card Waiting in the Sky! to your Itinerary

    CFF25: Budgens & Dragons: There's a Scratch card Waiting in the Sky!

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    29 May 2025Open 16:30 -

    Budgens & Dragons is an unfair, actual play, rogue-like, DnD-lite adventure with a very simple task: go to the local Budgens in Faringdon and buy Mother a scratch card. The catch is, the DM is trying to kill everyone before this happens.

  4. Add Phantoms of the Popera - Cheltenham to your Itinerary

    Phantoms of the Popera - Cheltenham

    Type

    Type:

    Theatre

    Imperial Square, Cheltenham

    Dates

    From:
    29 May 2025Open 19:30 - 21:30

    'Phantoms of the Popera' The biggest hits from the West End and Broadway - starring G4

  5. Add May Comedy Huddle at Smokey Joe's to your Itinerary

    May Comedy Huddle at Smokey Joe's

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    30 May 2025Open 19:40 - 22:00

    Join Smokey Joe's for a playful evening of sharing humour in a cosy space.

  6. Add CFF25: Phuckets & Rainbows to your Itinerary

    CFF25: Phuckets & Rainbows

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    30 May 2025Open 19:30 -

    Come and join Lizzie Bean for her first outing as a solo performer. Sharing her inspiring and illuminating story of a great unravelling to rediscover the light that shines.

  7. Add Wychwood Festival to your Itinerary

    Wychwood Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    30 May 2025to1 June 2025Various Opening Times

    Wychwood is an annual summer family festival which takes place at Cheltenham Racecourse. Nominated Best Family Festival at the UK Festival Awards, there is so much for all ages to enjoy and take part in. Wychwood Festival 2025 will take place 30 May…

  8. Add CFF25: Box of Frogs Improv Comedy to your Itinerary

    CFF25: Box of Frogs Improv Comedy

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    31 May 2025Open 19:30 -

    Hilarious scenes, sketches, songs, all based on suggestions from the audience.

  9. Add CFF25: Tabletop Role-Playing Game: The Musical! to your Itinerary

    CFF25: Tabletop Role-Playing Game: The Musical!

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    31 May 2025Open 16:30 -

    A brand-new, one-act musical about six adult friends playing a tabletop role-playing game, as the characters and their players navigate quests,

  10. Add CFF25: Box of Frogs Children's and Young People's Show to your Itinerary

    CFF25: Box of Frogs Children's and Young People's Show

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    31 May 2025Open 15:00 -

    Improvised fun and frolics with the odd song at Cheltenham Fringe Festival!

  11. Add 24-Hour Monologue at Cheltenham Playhouse to your Itinerary

    24-Hour Monologue at Cheltenham Playhouse

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    31 May 2025to1 June 2025Open 09:00 - 09:00

    Book yourself a wristband and gain access to Cheltenham Playhouse's entire 24-Hour Monologue. Support those brave performers who are putting themselves out there as they help raise vital funds to keep the Cheltenham Playhouse open and thriving for…

  12. Add CFF25: Macbeth/Lady Macbeth to your Itinerary

    CFF25: Macbeth/Lady Macbeth

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    1 June 2025Open 20:00 -

    Experience the psychological transformation of two intimately connected people as they search, in their own ways, for an elusive route to power.

  13. Add CFF25: Jaz Mattu: Forever to your Itinerary

    CFF25: Jaz Mattu: Forever

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    1 June 2025Open 19:30 -

    The lovable Kent comedian, Jaz Mattu, is back with his unique brand of absurdist, theatrical, multimedia stand-up comedy...forever.

  14. Add CFF25: New Beginnings to your Itinerary

    CFF25: New Beginnings

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    1 June 2025Open 18:00 -

    A nostalgic A-Level graduation party becomes a night of revelations, heartbreak, and self-discovery in New Beginnings.

  15. Add CFF25: Cotswold Comedy Collective to your Itinerary

    CFF25: Cotswold Comedy Collective

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    1 June 2025Open 17:30 -

    After sold-out shows at Stroud Sub Rooms, the Cotswold Comedy Collective are back to make you (hopefully) laugh!

  16. Add CFF25: FiddleBop Plays 'Gypsy Jazz Plus' to your Itinerary

    CFF25: FiddleBop Plays 'Gypsy Jazz Plus'

    Type

    Type:

    Music

    Cheltenham

    Dates

    From:
    1 June 2025Open 15:30 -

    FiddleBop play Gypsy Jazz Plus on violin, Spanish guitar, keyboard, fretless bass guitar, and with four voices in harmony.

  17. Add North By Northwest to your Itinerary

    North By Northwest

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    3 June 2025to7 June 2025Open 19:30 -

    When a mistimed phone call to his mother lands him smack bang in the middle of a Cold War conspiracy, Roger Thornhill finds himself on the run...

  18. Add Dunkertons Jazz Sessions with Kim Cypher to your Itinerary

    Dunkertons Jazz Sessions with Kim Cypher

    Type

    Type:

    Music

    Charlton Kings, Cheltenham

    Dates

    From:
    5 June 2025Open 19:30 - 22:00
    From:
    3 July 2025Open 19:30 - 22:00

    Book now for an evening with one of the UK's most exciting, vivacious, and highly respected saxophonists, vocalists and composers, Kim Cypher and her band. These special evenings of top-quality music normally sell out fast so don't delay!

  19. Add Roaring 1920's Fancy Dress Party (in aid of Dementia UK) to your Itinerary

    Roaring 1920's Fancy Dress Party (in aid of Dementia UK)

    Type

    Type:

    Charity

    Henrietta Street, Cheltenham

    Dates

    From:
    6 June 2025Open 19:00 - 01:00

    Roaring 1920's Fancy Dress Party at Brewhouse & Kitchen in aid of Dementia UK.

  20. Add ... Earnest? to your Itinerary

    ... Earnest?

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    10 June 2025to11 June 2025Open 19:30 -

    When a traditional production of Oscar Wilde's classic play gets underway, everything seems to be going perfectly to plan… that is, until the lead actor fails to arrive on cue and an actual audience member is chosen to star in the show.

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