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You are here: What's On > Monthly Highlights: > May
May 2026 - What's On Cheltenham Events
The sun is shining, bluebells are out in force, the sound of laughter in beer gardens has returned and there are two bank holidays to look forward to this month! Our round up below features the best Cheltenham events in May 2026, kicking off with the Cheltenham Jazz Festival followed by GWSRs Cotswold Festival of Steam and a wide variety of live shows, comedy acts and musicals. Scroll down for more May events inspiration.
For help planning the rest of your year check out our Cheltenham Festivals & Major Events Guide which features 30+ world-class events.
Plan your staycation in our Regency town with the help of these useful Cheltenham Weekend Breaks and Cheltenham Weekend Itineraries.
Event organisers - You can add your event for free to our what's on guide here.
