What's on in Cheltenham this month
We've gathered 42 events happening in Cheltenham between 26 Oct – 31 Oct across 22 venues — led by kids & family (8), music (7) and film & cinema (7), including 1 free-entry event. Click any event to see times, prices and book direct.
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Top picks this month
Hand-picked from 42 events
Owl Experiences
Sudeley Castle, Cheltenham
October Half Term: Ghosts, Pumpkins & Tudor Tales
Sudeley Castle, Cheltenham
Jeremy Bowen: Truth Under Fire
Cheltenham Town Hall, Cheltenham
All 42 events
Tuesday 30 October
12 events
Glhc Presents... Hardcore Halloween! Featuring Overpower!
The Frog & Fiddle, Cheltenham
Halloween Party with Tux Fizz
Dunkertons, Cheltenham
Drag Music Quiz
Cheltenham Playhouse, Cheltenham
Cocktail Masterclass
Malmaison Cheltenham, Cheltenham
Three Little Pirate Pigs
Everyman Theatre, Cheltenham
Cat Video Fest 2026
Cheltenham Playhouse, Cheltenham
Gary Davies 80s Party with Discos for Grown Ups
Cheltenham Town Hall, Cheltenham
Halloween Morning in Aid of WellChild
Elkstone Studios, Cheltenham
Paul Sinha Presents 2 Sinha Lifetime
Parabola Arts Centre, Cheltenham
The Debut
Hub 8 MX, Cheltenham
Paul Sinha: 2 Sinha Lifetime
Parabola Arts Centre, Cheltenham
Halloween Party
The Wilson, Cheltenham
Friday 26 October
2 eventsWednesday 31 October
16 events
House of Horrors Halloween Party
Tailors, Cheltenham
AI Panel
Hub 8 MX, Cheltenham
Musicals Spooky Karaoke Hosted by the West End Girls!
Smokey Joe's, Cheltenham
Oh My Drag! Presents... Frocky Horror Vol. 2 - a Halloween Drag Spooktacular!
The Frog & Fiddle, Cheltenham
Theodor von Holst by Candlelight
Holst Victorian House, Cheltenham
Ink
Hub 8 MX, Cheltenham
Flight Club's Halloween Haunted House Party
The Brewery Quarter, Cheltenham
Free Halloween Party
Clavell & Hind, Cheltenham
Spooky Specials
Gloucestershire Warwickshire Steam Railway, Cheltenham
Spooky Specials
Toddington Station, Cheltenham
Wallace & Gromit: The Curse of the Were-Rabbit
Hub 8 MX, Cheltenham
Fjord
Hub 8 MX, Cheltenham
Spooky Specials
Cheltenham Racecourse Station, Cheltenham
Synthetic Sincerity + the Last Screenwriter
Hub 8 MX, Cheltenham
After Dark at Sudeley Castle: a Victorian Murder Mystery
Sudeley Castle, Cheltenham
Cotswold Horse Fun Rides
Cotswold Farm Park, Cheltenham
Monday 29 October
4 events
The Howlers
Cheltenham Playhouse, Cheltenham
Halloween Hootenanny III - Ft. Convey // Hollowkin // Azaleas // Della Nova
The Frog & Fiddle, Cheltenham
The Three Little Pigs
Cheltenham Playhouse, Cheltenham
Simon Brodkin: Unleashed
Cheltenham Town Hall, Cheltenham
Saturday 27 October
5 eventsJeremy Bowen: Truth Under Fire
Cheltenham Town Hall, Cheltenham
A Night of Whitney Houston
The Ivy Montpellier Brasserie, Cheltenham
Dracula - The Panto!
Everyman Theatre, Cheltenham
We Will Rock You
Everyman Theatre, Cheltenham
Dwaec Animal Show
Dunkertons, Cheltenham
Sunday 28 October
3 eventsA Taste of Tuscany
Belgrave House Settebello, Cheltenham
Strange Tales for Halloween
Parabola Arts Centre, Cheltenham
Creative Explorers: October Half-Term
The Wilson, Cheltenham
Looking for events outside this month? Browse all 389+ upcoming events in Cheltenham →
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