A collage of Cheltenham happens in May

May 2025 - What's On Cheltenham Events

Highlights

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,…

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…

People stood next to big JAZZ sign.

Cheltenham Jazz Festival... around town free gigs

Keep Wednesday 30 April to Monday 6 May free to enjoy five days of free gigs on the Cheltenham Jazz…

Cheltenham Playhouse

Cheltenham Fringe Festival

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

Number of results:

Number of results: 13

Featured Events

  1. Add Cheltenham Jazz Festival... around town free gigs to your Itinerary

    Cheltenham Jazz Festival... around town free gigs

    Type

    Type:

    Free

    Cheltenham

    Dates

    From:
    30 Apr 2025to5 May 2025

    Keep Wednesday 30 April to Monday 6 May free to enjoy five days of free gigs on the Cheltenham Jazz Festival Free Stage in Montpellier Gardens and in Cheltenham’s streets, pubs and clubs.

  2. Add Cheltenham Craft Market to your Itinerary

    Cheltenham Craft Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    18 May 2025

    Located along Cheltenham Promenade, the monthly Cheltenham Crafts Market brings together local producers, craftspeople and artisans to create a market full of unique gifts, homeware and handmade goods.

  3. 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…

  4. 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.

Ongoing Events

  1. Add Primrose Vale - Pick Your Own to your Itinerary

    Primrose Vale - Pick Your Own

    Type

    Type:

    Seasonal

    Cheltenham

    Dates

    From:
    1 May 2025to31 Oct 2025Various Opening Times

    The Pick Your Own fields open from late May until October.

  2. Add Dear Evan Hansen to your Itinerary

    Dear Evan Hansen

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    6 May 2025to10 May 2025Open 19:30 -

    Meet Evan: an anxious high school kid who wants nothing more than to fit in. The thing is, on his way to fitting in, he didn't tell the whole truth. And now must give up on a life he never dreamt he'd have. As events spiral and the truth comes out,…

  3. Add Cheltenham Antiques & Vintage Market to your Itinerary

    Cheltenham Antiques & Vintage Market

    Type

    Type:

    Antiques

    Cheltenham

    Dates

    From:
    11 May 2025

    Your opportunity to browse antiques, collectables, vintage products, home decor, porcelain, jewellery, furniture and art once a month along Cheltenham Promenade.  

  4. Add Beginners Dry Stone Walling Courses at Notgrove to your Itinerary

    Beginners Dry Stone Walling Courses at Notgrove

    Type

    Type:

    Workshop

    Notgrove, Cheltenham

    Dates

    From:
    17 May 2025to18 May 2025Open 09:00 - 16:30

    Dry stone walling courses for beginners at Notgrove suitable for anyone 16 years and older. Run by DSWA instructor with years of experience, Richard Gray at Notgrove over two days. Accommodation at Notgrove available on site. Price is £199 pp.

  5. Add Steak Day at Tailors to your Itinerary

    Steak Day at Tailors

    Type

    Type:

    Food and Drink

    Cheltenham

    Dates

    From:
    19 June 2024to15 Oct 2025Open 12:00 - 21:00

    Steak Day at Tailor's. Starting Wednesday 19th June, every Wednesday 12pm-9pm

  6. Add Cavendish House Independent Pop up Market & Food Hall to your Itinerary

    Cavendish House Independent Pop up Market & Food Hall

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    26 June 2024to1 July 2025Various Opening Times

    Cavendish House is a host to an Independent Pop Up Market & Food Hall with nearly 50 small businesses trading.

  7. Add Turning The Pages to your Itinerary

    Turning The Pages

    Type

    Type:

    Historical

    Pittville, Cheltenham

    Dates

    From:
    9 July 2024to31 Dec 2026Open 10:00 - 16:00

    Explore Holst's manuscripts on innovative Turning The Pages software.

  8. Add Murder On The Orient Express to your Itinerary

    Murder On The Orient Express

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    29 Apr 2025to3 May 2025Open 19:30 -

    Winter 1934 and an avalanche stops The Orient Express dead in its tracks. A murder. A train full of suspects. An impossible case. Trapped in the snow with a killer still on-board, can the world's most famous detective, Hercule Poirot, crack the case…

  9. Add Cheltenham Jazz Festival to your Itinerary

    Cheltenham Jazz Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    30 Apr 2025to5 May 2025Various Opening Times

    Cheltenham, The Festival Town, is home to one of the country’s best-loved jazz festivals, attracting over 20,000 music fans annually. The popular annual event will next take place 30 April - 5 May 2025.

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