A collage of Cheltenham happens in May

May 2026 - 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,…

People stood next to big JAZZ sign.

Cheltenham Jazz Festival... around town free music

Keep Wednesday 29 April to Monday 4 May 2026 clear in your calendar to enjoy six days of free…

Race Night at Cheltenham Racecourse

Race Night ft. Hunter Chase Racing

The curtain comes down on the racing season with Cheltenham’s only evening fixture. The evening…

Number of results:

Number of results: 4

Featured Events

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

    Cheltenham Jazz Festival... around town free music

    Type

    Type:

    Free

    Cheltenham

    Dates

    From:
    29 Apr 2026to4 May 2026

    Keep Wednesday 29 April to Monday 4 May 2026 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…

Ongoing Events

  1. Add Race Night ft. Hunter Chase Racing to your Itinerary

    Race Night ft. Hunter Chase Racing

    Type

    Type:

    Horse Racing

    Prestbury, Cheltenham

    Dates

    From:
    1 May 2026Various Opening Times

    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…

  2. Add Cheltenham Antiques & Vintage Market to your Itinerary

    Cheltenham Antiques & Vintage Market

    Type

    Type:

    Antiques

    Cheltenham

    Dates

    From:
    10 May 2026

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

  3. Add Cheltenham Jazz Festival to your Itinerary

    Cheltenham Jazz Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    29 Apr 2026to4 May 2026Various 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 29 April - 6 May 2026.

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