| Date | Event | Venue |
|---|---|---|
| 05 Sep 2025 | Josh Butler in Chepstow | Piercefield Park, Caldicot |
| 25 Jul 2025 | Swing from Paris at the Drill Hall Chepstow 25 July | The Drill Hall Chepstow, Caldicot |
| 19 Jul 2025 | Forever Hounds Trust at Chepstow Festival of Arts | Priory Church of St Mary, Chepstow, Caldicot |
| 01 Aug 2025 | Formidable Vegetable Mal Webb & Kylie Morrigan Green Gathering | Green Gathering!!, Caldicot |
| 09 Aug 2025 | Chepstow Show | Chepstow Racecourse, Caldicot |
| 21 Aug 2025 | Florence Black LIVE at Chepstow Castle | Chepstow Castle, Caldicot |
| 31 Jul 2025 | The Green Gathering 2025 | Piercefield Park, Caldicot |
| 28 Sep 2025 | WAYNES WORLD (PG) - Real Ale & Cider Festival | Chepstow Real Ale & Cider Festival, Caldicot |
| 24 Jan 2026 | Chepstow Wassail and Mari Lwyd. Hosted by Widders Border Morris | Chepstow Town Centre, Caldicot |
| 25 Aug 2025 | Summer outdoor Kids fest new date | Sudbrook Cricket Club, Caldicot |
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