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Cheltenham Jazz Festival Guide

The highlights, the best bits, the jazziest jazz on the schedule

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Cheltenham Jazz Festival is back! Spread over 16 May and nicely falling over the first of two May bank holiday weekends, we reckon this edition of the festival is going to be the best.

With a performance schedule as rich as the voices of Ella Fitzgerald, Louis Armstrong and Billie Holiday combined, we’ve selected the best performance to book on each day of the festival, to make planning your time there much easier.

Wednesday 1 May

Jamie Cullum

Find Grammy, Golden Globe and Brit award winner Jamie Cullum performing hits from his new album at Cheltenham Jazz Festival, his first reappearance since his sellout show back in 2016. Tickets start at £30, buy here.

Thursday 2 May

Buck & Billie

The Buck Clayton Legacy Band joins Billie Holiday interpreter vocalist Julia Biel for a performance showcasing the treasure trove of hits created in the collaboration between Billie Holiday and Buck Clayton. Tickets cost £65, book here.

Friday 3 May

Judi Jackson

One for emerging talent lovers; this performance is by Judi Jackson, who’s been taking the jazz scene by storm, headlining sellout shows in London’s XOYO and Jazz Café, Ronnie Scott’s and the Roundhouse. Tickets cost £65, book here.

Saturday 4 May

Abdullah Ibrahim & Ekaya

South African pianist Abdullah Ibrahim has been an influential figurehead of the jazz industry for over 50 years. In this performance, he’ll be joined with his band Ekaya to release music from his brand new album. Tickets start at £20, book here.

Sunday 5 May

Double Bill: Yola & Kizzy Crawford

Since performing with Massive Attack and featuring on Jools Holland’s Hootennany, Yola’s voice has been recognised as a fantastic addition to jazz, and has been compared to the likes of Dolly Parton and the Staples Singers. Kizzy Crawford combines soul and folk with jazz and has been applauded recently on BBC Radio 2 for her talent. Tickets start at £12, book here.

Monday 6 May

National Youth Jazz Orchestra

What better way to wave goodbye to another year of fabulous jazz at Cheltenham Jazz Festival than with a performance by the 18 peice National Youth Jazz Orchestra? This year, directed by Mark Armstrong, the orchestra will perform music celebrating women in jazz. Tickets cost £16, book here. 

Find the full programme of performances at

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