A colourful collage of Cheltenham Festivals

Cheltenham Festivals & Major Events Guide 2025

Highlights

Pittville Pump Room

The Holst 150 Birthday Party

Celebrate Cheltenham's most famous son, composer Gustav Holst, at a day of fun activities and music…

Fresh: Art Fair

Fresh: Art Fair

Fresh: Art Fair shows a wider range of art than any art fair outside London.  From exciting new…

Cheltenham Observation Wheel

Cheltenham Observation Wheel

Soar above Cheltenham this Easter on a spectacular observation wheel, offering breathtaking…

The April Meeting at Cheltenham Racecourse

The April Meeting

It's no easy task following Cheltenham Festival however, April’s two-day meeting is the perfect…

Number of results:

Number of results: 36

, currently showing 1 to 20.

  1. Pittville Pump Room

    Add The Holst 150 Birthday Party to your Itinerary

    The Holst 150 Birthday Party

    Type

    Type:

    Music

    Cheltenham

    Dates

    From:
    29 Mar 2025Open 14:00 - 21:30

    Celebrate Cheltenham's most famous son, composer Gustav Holst, at a day of fun activities and music at Pittville Pump Room this spring.

  2. Fresh: Art Fair

    Add Fresh: Art Fair to your Itinerary

    Fresh: Art Fair

    Type

    Type:

    Art

    Cheltenham

    Dates

    From:
    3 Apr 2025Open 17:30 - 21:00
    From:
    4 Apr 2025to6 Apr 2025Various Opening Times

    Fresh: Art Fair shows a wider range of art than any art fair outside London.  From exciting new talent to famous names like Picasso, Banksy, Matisse and Miro this event brings you art from as little as £50 to £20,000 or more, but most well within…

  3. Cheltenham Wine Festival

    Add Cheltenham Wine Festival to your Itinerary

    Cheltenham Wine Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    5 Apr 2025Various Opening Times

    Join wine lovers in the Cheltenham Ladies College to explore and taste from a wide choice of exciting wines at the Cheltenham Wine Festival. Enjoy your favourites and have fun discovering new ones from countries such as England, France, Italy,…

  4. Cheltenham Observation Wheel

    Add Cheltenham Observation Wheel to your Itinerary

    Cheltenham Observation Wheel

    Type

    Type:

    Family

    Cheltenham

    Dates

    From:
    12 Apr 2025to5 May 2025Open 12:00 - 21:00

    Soar above Cheltenham this Easter on a spectacular observation wheel, offering breathtaking panoramic views from 12th April to 5th May.

  5. The April Meeting at Cheltenham Racecourse

    Add The April Meeting to your Itinerary

    The April Meeting

    Type

    Type:

    Horse Racing

    Prestbury Park, Cheltenham

    Dates

    From:
    16 Apr 2025to17 Apr 2025

    It's no easy task following Cheltenham Festival however, April’s two-day meeting is the perfect time to reflect on achievements and remember that racing, no matter the event, is competitive and above all else, a joyous occasion.

  6. People stood next to big JAZZ sign.

    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 5 May 2025 clear in your calendar to enjoy six days of free music, part of the Cheltenham Jazz Festival. Featuring the best of local talent performing at venues across Cheltenham - completely free of charge, thanks…

  7. Crowds at Cheltenham Jazz Festival 2024.

    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.

  8. Race Night at Cheltenham Racecourse

    Add Race Night ft. Hunter Chase Racing to your Itinerary

    Race Night ft. Hunter Chase Racing

    Type

    Type:

    Horse Racing

    Prestbury, Cheltenham

    Dates

    From:
    2 May 2025

    The curtain comes down on the racing season with Cheltenham’s only evening fixture. The evening hosts a fun vibe from start to finish, you can feel the party atmosphere as soon as you walk through those gates onto the sacred grounds of Cheltenham…

  9. Cheltenham Poetry Festival

    Add Cheltenham Poetry Festival to your Itinerary

    Cheltenham Poetry Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    7 May 2025to17 May 2025Various Opening Times

    Cheltenham Poetry Festival offers an annual 10-day programme of exciting live literature events each spring and a year-round online programme of workshops and poetry lounges. The 2025 Cheltenham Poetry Festival will take place 7 - 17 May at venues…

  10. Cheltenham Festival of Performing Arts

    Add Cheltenham Festival of Performing Arts to your Itinerary

    Cheltenham Festival of Performing Arts

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    9 May 2025to17 May 2025

    Cheltenham's oldest festival, set up in 1926! The annual Cheltenham Festival of Performing Arts is packed with performances in music, dance and drama by children from local schools, theatre groups, dance schools and music clubs...

  11. Pride in Cheltenham

    Add Pride in Cheltenham to your Itinerary

    Pride in Cheltenham

    Type

    Type:

    LGBTQ+

    Cheltenham

    Dates

    From:
    17 May 2025Open 12:00 - 18:00

    Celebrate the spirit of inclusivity and love at Pride in Cheltenham 2025! This annual event features fun inclusive activities for all ages. Whether you're part of the LGBTQ+ community or a supportive ally, join us on Saturday 17 May to share in the…

  12. Cotswold Festival of Steam

    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…

  13. Cheltenham Playhouse

    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.

  14. Gloucestershire Cheese Rolling on Coopers Hill

    Add Gloucestershire Cheese Rolling on Coopers Hill to your Itinerary

    Gloucestershire Cheese Rolling on Coopers Hill

    Type

    Type:

    Competition/Game

    Gloucester

    Dates

    From:
    26 May 2025Open 12:00 -

    The world-famous Gloucestershire Cheese Rolling returns on Monday 26 May 2025, bringing thrilling action and quirky tradition back to Cooper’s Hill near Gloucester. Every year, thousands of spectators and daring competitors flock to this iconic…

  15. Wychwood Festival

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    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…

  16. Cheltenham Science Festival

    Add Cheltenham Science Festival to your Itinerary

    Cheltenham Science Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    3 June 2025to8 June 2025

    This popular annual festival brings together the UK’s most respected scientists, favourite science communicators, writers, and artists to talk about today’s hottest topics. 

  17. Cheltenham Running Festival

    Add Cheltenham Running Festival to your Itinerary

    Cheltenham Running Festival

    Type

    Type:

    Running

    Evesham Road, Cheltenham

    Dates

    From:
    8 June 2025

    This event offers you the unique opportunity to run a 5k, 10k or Half Marathon around the famous Cheltenham Racecourse!

  18. Gloucestershire Warwickshire Railway Real Ale Festival

    Add Gloucestershire Warwickshire Railway Real Ale Festival to your Itinerary

    Gloucestershire Warwickshire Railway Real Ale Festival

    Type

    Type:

    Railway / Train Events

    Cheltenham

    Dates

    From:
    13 June 2025to15 June 2025Open 09:00 - 17:00

    Get ready for a journey back in time, where vintage locomotives and the finest brews come together in perfect harmony.

  19. A man overlooking Cheltenham from Leckhampton Hill

    Add Cheltenham's Three Peaks Challenge to your Itinerary

    Cheltenham's Three Peaks Challenge

    Type

    Type:

    Event

    Cheltenham

    Dates

    From:
    14 June 2025Open 06:30 - 18:30

    The 22 mile walk which starts at their Charity 'HQ' in Lansdown Parade, provides you with the opportunity to take part in an exhausting but exhilarating adventure through Gloucestershire's most picturesque landscapes.

  20. Cheltenham Food and Drink Festival 2021

    Add Cheltenham Food & Drink Festival to your Itinerary

    Cheltenham Food & Drink Festival

    Type

    Type:

    Food and Drink

    Cheltenham

    Dates

    From:
    20 June 2025to22 June 2025

    Pamper your palate and join family and friends over one great three-day weekend to celebrate Cheltenham Food & Drink Festival. Enjoy live music, free wine tasting talks, cheese tasting, artisan food producers, along with a myriad of demonstrations…

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Remove Product from ItineraryCheltenham Festival of Performing Arts