Collage of Cheltenham festivals and events

What's On in Cheltenham 2025 - Monthly Highlights

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This Month

Cheltenham Farmers Market

Cheltenham Farmers Market

LocationCheltenham

Openings

Season

9th May 2025-29th May 2026

Season

25th July 2025

On the second and last Friday of every month stalls line Cheltenham Promenade selling a…

Lions at Large - The Pride of Gloucestershire Trail

Lions at Large - The Pride of Gloucestershire Trail

LocationCheltenham

Openings

Season

11th July 2025-14th September 2025

Lions at Large – The Pride of Gloucestershire Trail has roared onto the streets of…

Sulzer Type 2 image by Martin Loader

Summer Diesel Gala at GWSR

LocationCheltenham

Openings

Season

25th July 2025-27th July 2025

Get ready for a weekend of thrilling locomotives, nostalgic journeys, and unforgettable…

Summer Jam: The Lakefest Warmup

Summer Jam: The Lakefest Warmup

LocationCheltenham

Openings

Entertainment timings

25th July 2025-27th July 2025

The popular free music festival at The Brewery Quarter returns to kick start the summer…

The Suffolks Sunday Market

The Suffolks Sunday Market

LocationCheltenham

Openings

Featuring dog show

27th July 2025

These fantastically-popular Street Fairs in the Suffolks are always great events. Whether…

Teddy Bear

Teddy Bear Thursday

LocationGloucestershire, Cheltenham

Openings

Season

31st July 2025

Pop along to the GWSR in August see the Teddy Bears come out for a picnic on Teddy Bear…

Statues