What's on in Cheltenham May 2026
We've gathered 100 events happening in Cheltenham between 1 May – 31 May across 33 venues — led by music (63), kids & family (9) and other (8), including 1 free-entry event. Click any event to see times, prices and book direct.
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Top picks may 2026
Hand-picked from 100 eventsAll 100 events
China Moses
Parabola Arts Centre, Cheltenham
Taj Farrant
Dunkertons, Cheltenham
Flower Moon Swim
Cheltenham Lido, Cheltenham
Children’s Trail: Maypole Mystery Tour
Holst Victorian House, Cheltenham
Not A Cult - Roll with the Punch II
Smokey Joe's, Cheltenham
Gotts Street Park
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
BLACKSABBATHMODE
Parabola Arts Centre, Cheltenham
Jessie J
Big Top (Cheltenham Jazz Festival), Cheltenham
Cheltenham Jazz Festival - Day three free events
Various Venues: Cheltenham, Cheltenham
Thieves // Death is a Girl // Red Swan // Future Phantoms
The Frog & Fiddle, Cheltenham
They All Came Out to Montreux
Cheltenham Ladies' College, Cheltenham
Nigel Kennedy
Cheltenham Town Hall, Cheltenham
Joshua Redman
Cheltenham Town Hall, Cheltenham
Bill Frisell and Eyvind Kang
Cheltenham Town Hall, Cheltenham
Emma-Jean Thackray
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
Discover Kathak with Sonia Sabri
Montpellier Gardens, Cheltenham
Nectar Woode Supported by Aria Soul
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
Sarah Gillespie & Chris Montague
Hotel du Vin, Cheltenham
Bassix: Crissy Criss, Eksman & ACP
Under The Prom, Cheltenham
Solomon Hicks
Dunkertons, Cheltenham
Matt Carmichael
Parabola Arts Centre, Cheltenham
Cheltenham Jazz Festival - Day four free events
Various Venues: Cheltenham, Cheltenham
Joss Stone
Big Top (Cheltenham Jazz Festival), Cheltenham
The Power of Four
Parabola Arts Centre, Cheltenham
Theon Cross
Parabola Arts Centre, Cheltenham
Mica Paris with Ronnie Scott's Jazz Orchestra
Big Top (Cheltenham Jazz Festival), Cheltenham
Friends of Pittville Plant Sale
Pittville Park, Cheltenham
Ava Joe
Dunkertons, Cheltenham
Ladies of Midnight Blue
Parabola Arts Centre, Cheltenham
ABC
Big Top (Cheltenham Jazz Festival), Cheltenham
Jazz Kids!
Montpellier Gardens, Cheltenham
Tinariwen
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
Royal Birmingham Conservatoire and Siena/Hamburg Collab
Parabola Arts Centre, Cheltenham
Tots Tunes with Tara Franks
Montpellier Gardens, Cheltenham
The Puppini Sisters
Cheltenham Town Hall, Cheltenham
Robinson Khoury
Parabola Arts Centre, Cheltenham
The Earth Wind and Fire Experience by Al McKay
Big Top (Cheltenham Jazz Festival), Cheltenham
Afro-Latin Adventures: Ladies of Midnight Blue
Montpellier Gardens, Cheltenham
Courtney Pine
Cheltenham Town Hall, Cheltenham
Giacomo Smith
Dunkertons, Cheltenham
Family Sing with Aga Serugo-Lugo
Montpellier Gardens, Cheltenham
Camilla George
Parabola Arts Centre, Cheltenham
Family Cèilidh
Montpellier Gardens, Cheltenham
Georgia Cécile: American Songbook
Cheltenham Town Hall, Cheltenham
Miles Davis Symphonic: Kind of Blue
Big Top (Cheltenham Jazz Festival), Cheltenham
Harwood Dance
The Bacon Theatre, Cheltenham
Gentleman's Dub Club
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
Cheltenham Jazz Festival - Day five free events
Various Venues: Cheltenham, Cheltenham
Corinne Bailey Rae
Big Top (Cheltenham Jazz Festival), Cheltenham
Lady Blackbird
Cheltenham Town Hall, Cheltenham
Makaya McCraven
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
Blue Lab Beats
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
Elysia Biro
Dunkertons, Cheltenham
Yazz Ahmed
Parabola Arts Centre, Cheltenham
Emma Rawicz
Parabola Arts Centre, Cheltenham
Alice Zawadzki
Montpellier Gardens, Cheltenham
Kim Cypher feat. Ashley Slater
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
10cc's Graham Gouldman & Heart Full of Songs
Big Top (Cheltenham Jazz Festival), Cheltenham
Suntou Susso
Montpellier Gardens, Cheltenham
The Big Benhall Yard Sale
Benhall Woods and Park, Cheltenham
Jalen Ngonda
Big Top (Cheltenham Jazz Festival), Cheltenham
The Big Benhall Yard Sale
Various Venues, Benhall, Cheltenham
Cheltenham Jazz Festival - Day six free events
Various Venues: Cheltenham, Cheltenham
Roberto Fonseca: La Gran Diversion
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
The Paint Club painting party
The Bottle of Sauce, Cheltenham
Jack Savoretti
Big Top (Cheltenham Jazz Festival), Cheltenham
The Big Family Gig
The DEYA Arena (Cheltenham Jazz Festival), Cheltenham
Legend - The Music Of Bob Marley
Everyman Theatre, Cheltenham
Tuesday Book Group - Fundamentally by Nussaibah Younis
The Terrace, Cheltenham
Man In The Mirror
Everyman Theatre, Cheltenham
Cheltenham Festival of Performing Arts
Cheltenham Town Hall, Cheltenham
The Beefy Boys in conversation
Waterstones, Cheltenham
Prescott Hill Climb School
Prescott Hill Climb, Cheltenham
Dom Joly's Speakeazy
The Steam and Whistle, Cheltenham
Medical Information Lecture: A Path to a Healthy Body and Soul through the Teaching of Bruno Groening - Cheltenham
Cheltenham Friends' Meeting House, Cheltenham
Thursday Book Group - Fundamentally Nussaibah Younis
The Terrace, Cheltenham
Come Together: The Lennon and McCartney Songbook
Everyman Theatre, Cheltenham
Metal 2 the Masses - Heat 3
The Frog & Fiddle, Cheltenham
Cheltenham Chamber Orchestra: French Connections
St Andrew's Church, Cheltenham
Groundbreaking Women: History Of Art Lecture
The Wilson, Cheltenham
Sanctuary - A Night Of Classic Ibiza & House Anthems
The Apartment, Cheltenham
Prescott Italia, supported by Auto Italia Magazine
Prescott Hill Climb, Cheltenham
Expressive Drawing: Inspired by Rego
The Wilson, Cheltenham
Drag Wars 2026 - Grand Final
The Frog & Fiddle, Cheltenham
Passed Out // Uncertainty // Spiruline // Circumvent
The Frog & Fiddle, Cheltenham
Classics at Prescott
Prescott Hill Climb, Cheltenham
Chuckl Presents: Larry Dean, Marcus Brigstocke, Eshaan Akbar and Laura Lexx
Everyman Theatre, Cheltenham
The World at Our Feet
Dean Close School, Cheltenham
Moran's Junior Aquathlon & Triathlon
Cheltenham Lido, Cheltenham
The Detective Dog
Cheltenham Playhouse, Cheltenham
Victorian Book Group: Vilette by Charlotte Bronte
Holst Victorian House, Cheltenham
Josh Widdicombe
Cheltenham Town Hall, Cheltenham
Robin Nolan Trio - For the Love of George
The Steam and Whistle, Cheltenham
Birmingham Royal Ballet: Carlos Acosta's Ballet Celebration
Everyman Theatre, Cheltenham
A Guy Called Gerald - Live In Session at DEYA Brewery
DEYA Brewing Company, Cheltenham
An Evening with Eloise Kane
Hatchards, Cheltenham
The Water Babies
Cheltenham Playhouse, Cheltenham
Cheltenham Pride
Imperial Gardens, Cheltenham
Ed Force One
The Frog & Fiddle, Cheltenham
Big Sis DJs House Party
DEYA Brewing Company, Cheltenham
Looking for events outside May 2026? Browse all 403+ upcoming events in Cheltenham →
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