Events in Cheltenham From 25th May – 31st May 2026

This week in Cheltenham, from May 24th to May 31st, offers a mix of events suited to different preferences. You can find live music, creative workshops, and outdoor activities. The town’s Regency-era architecture and history as a spa town since 1716 shape much of its current identity. You can follow the paths of Captain Skillicorne and walk through the historic centre. For events, you can find music at Smokey Joe’s and The Alchemist Bar & Restaurant. The Blue Moon Swim at Cheltenham Lido takes place under the full moon on May 31st. Check listings for times and locations. Travel by rail via Cheltenham Spa railway station or by car using the A40 trunk road, though be mindful of traffic disruption during large events. You can find a relaxed evening out or something a little different. A short drive away, the Sandford Parks Lido is open but has poorly maintained changing rooms. The Cheltenham Racecourse has overhanging floors that block views. For events, avoid the Pittville Pump Room café as it’s closed during the wedding fayre. For reliable access, use the Great Western Railway or plan ahead for parking, especially during the Cheltenham Festival.