Events in Cheltenham From 11th May – 17th May 2026

This week in Cheltenham features a mix of live music, comedy, and cultural workshops, with opportunities to connect with locals and explore the town’s heritage. You can find stand-up shows at the Everyman Theatre and Cheltenham Town Hall, or enjoy a creative painting session at The Bottle of Sauce. Local bands perform at The Steam and Whistle, and events like the Robin Nolan Trio bring music to community spaces. For professionals, networking meet-ups take place at The SiTE and Clockwise Cheltenham. There’s also an artisan cheese and wine evening at The Strand, and a talk on natural history at Hatchards. Community events, like the Cheltenham Food Bank at The Pavilion and a quiz night at Gotherington Old Chapel, offer chances to engage with local initiatives. Cheltenham has been a spa town since 1716, and its railway connections via Cheltenham Spa station and Great Western Railway make it accessible for evening outings. Events often align with cultural festivals or heritage themes, such as those linked to the Gloucestershire & Warwickshire Railway. Be mindful of traffic disruption during larger events, consider using rail travel instead of driving. Check the listings below for venue details and timings.