A collage of Cheltenham happens in May

May 2025 - What's On Cheltenham Events

Highlights

Cheltenham Fringe Festival 2025 poster

Cheltenham Fringe Festival

A festival celebrating a wide variety of art, including music, theatre, film, drag, poetry, comedy…

Cotswold Festival of Steam

Cotswold Festival of Steam

Get ready to embark on a journey through time, where the past comes alive and the heritage of steam…

Exterior of John Lewis store

May events at John Lewis Cheltenham

Join the John Lewis Cheltenham team this May for masterclasses with their inhouse experts. 

Number of results:

Number of results: 70

, currently showing 1 to 20.

Featured Events

  1. Add May events at John Lewis Cheltenham to your Itinerary

    May events at John Lewis Cheltenham

    Type

    Type:

    Health & Wellbeing

    Cheltenham

    Dates

    From:
    21 May 2025to24 May 2025

    Join the John Lewis Cheltenham team this May for masterclasses with their inhouse experts. 

  2. Add Cotswold Festival of Steam to your Itinerary

    Cotswold Festival of Steam

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    24 May 2025to26 May 2025Open 09:00 - 17:00

    Get ready to embark on a journey through time, where the past comes alive and the heritage of steam locomotives is celebrated in all its glory. Join for a long bank holiday weekend filled with the magic of steam, picturesque landscapes, and the rich…

  3. Add Retrospective of House presents Howard Donald (DJ set) to your Itinerary

    Retrospective of House presents Howard Donald (DJ set)

    Type

    Type:

    Music

    Tewkesbury Road, Elmstone Hardwicke,Cheltenham

    Dates

    From:
    24 May 2025Open 17:00 - 23:00

    Howard Donald in Cheltenham

  4. Add Prescott Historique to your Itinerary

    Prescott Historique

    Type

    Type:

    Sports

    Cheltenham

    Dates

    From:
    24 May 2025to25 May 2025Various Opening Times

    Prescott Historique celebrates the history of British Hill Climbing, in the only Pre-war motorsport venue in Gloucestershire and this years event will showcase some of the most iconic competition cars ever.

  5. Add Cheltenham Lido 90th Birthday Party to your Itinerary

    Cheltenham Lido 90th Birthday Party

    Type

    Type:

    Family

    Cheltenham

    Dates

    From:
    25 May 2025Open 11:00 - 14:00

    ​​​​​​​Join Cheltenham Lido on Sunday the 25th of May as they celebrate Cheltenham Lido’s 90th Birthday in true summer style!

  6. Add The Suffolks Sunday Market to your Itinerary

    The Suffolks Sunday Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    25 May 2025Open 11:00 - 16:00

    These fantastically-popular Street Fairs in the Suffolks are always great events. Whether it’s the May Bank Holiday or the Christmas Market, there’s always a lovely friendly atmosphere, great products on sale and lots of fun entertainment.

  7. Add Cheltenham Fringe Festival to your Itinerary

    Cheltenham Fringe Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    26 May 2025to1 June 2025

    A festival celebrating a wide variety of art, including music, theatre, film, drag, poetry, comedy and more.

  8. 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…

  9. Add Cheltenham Farmers Market to your Itinerary

    Cheltenham Farmers Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    30 May 2025

    On the second and last Friday of every month stalls line Cheltenham Promenade selling a range of produce including various meats and charcuterie, fruit and vegetables, desserts, preserves and pickles, cakes, bread, cheese and plants...

Ongoing Events

  1. Add Huey Morgan The Fun Lovin' Criminal Live to your Itinerary

    Huey Morgan The Fun Lovin' Criminal Live

    Type

    Type:

    Music

    Charlton Kings, Cheltenham

    Dates

    From:
    21 May 2025Open 19:30 - 23:00

    Cheltenham Jazz Festival in collaboration with Dunkertons Park presents: Huey Morgan The Fun Lovin Criminal.
    The King of New York, Mr Huey Morgan is back with his brand new band – Huey Morgan The Fun Lovin Criminal

  2. Add Author Talk - Antonia Hodgson to your Itinerary

    Author Talk - Antonia Hodgson

    Type

    Type:

    Poetry & Literature

    Cheltenham

    Dates

    From:
    22 May 2025Open 18:00 - 20:00

    Join Waterstones in conversation with Antonia Hodgson, discussing her new fantasy novel 'The Raven Schloar'

  3. Add Nikita Kuzman: Midnight Dancer to your Itinerary

    Nikita Kuzman: Midnight Dancer

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    22 May 2025to24 May 2025Open 19:30 -

    Rising Star of Strictly Come Dancing and Celebrity Big Brother Nikita Kuzmin brings his brand-new show, Midnight Dancer to the stage on his first ever solo UK and Ireland Tour.

  4. Add This is Country Unplugged to your Itinerary

    This is Country Unplugged

    Type

    Type:

    Music

    Charlton Kings, Cheltenham

    Dates

    From:
    22 May 2025Open 19:00 - 23:00

    After their incredible sold-out "This is Country" show in April, The Reckless Breed return by popular demand to Dunkertons—this time for an unforgettable acoustic night of country hits.

  5. Add Chocolate Love Match at HotelChocolat to your Itinerary

    Chocolate Love Match at HotelChocolat

    Type

    Type:

    Food and Drink

    Cheltenham

    Dates

    From:
    23 May 2025Open 13:00 - 13:30
    From:
    23 May 2025Open 14:00 - 14:30

    Book now to secure a space on HotelChocolat's personal tasting experience, to reveal your ultimate flavour profile.

  6. Add Music in Country Churches to your Itinerary

    Music in Country Churches

    Type

    Type:

    Concert

    Chedworth, Cheltenham

    Dates

    From:
    23 May 2025to24 May 2025Open 18:30 - 20:00

    Classical concert

  7. Add Paint & Pudding with Paint Pot Parties to your Itinerary

    Paint & Pudding with Paint Pot Parties

    Type

    Type:

    Art

    Elkstone, Cheltenham

    Dates

    From:
    23 May 2025Open 18:00 - 22:00

    Tote bag painting the the Tipi at Elkstone Studios with delicious puddings!

  8. Add Wizards, Witches and Warriors to your Itinerary

    Wizards, Witches and Warriors

    Type

    Type:

    Concert

    Imperial Square, Cheltenham

    Dates

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

    To include the music of: Game of Thrones, World of Warcraft, Lord of the Rings, Firebird Suite, Sorcerer's Apprentice … and many more!

  9. Add Candles & Cream Tea to your Itinerary

    Candles & Cream Tea

    Type

    Type:

    Crafts

    Elkstone, Cheltenham

    Dates

    From:
    24 May 2025Open 10:40 - 12:40

    Candle Making and Cream Tea.

  10. Add Cotswold 100 Sportive to your Itinerary

    Cotswold 100 Sportive

    Type

    Type:

    Sporting

    Prestbury, Cheltenham

    Dates

    From:
    24 May 2025Various Opening Times

    The Cotswolds 100 sportive (In its 6th Year) starting and finishing at Cheltenham Racecourse will take in much of the stunning Cotswolds AONB on the cycle routes.

  11. Add KickBack Live at Tailors to your Itinerary

    KickBack Live at Tailors

    Type

    Type:

    Music

    Cheltenham

    Dates

    From:
    24 May 2025Open 20:00 - 22:30

    Kickback Playing Live

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