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| Date | Event | Venue |
|---|---|---|
| 22 Aug 2025 | Ben Monder in Westport | The Mill, Westport |
| 10 Aug 2025 | The Wood Brothers in Westport | The Levitt Pavilion for the Performing Arts, Westport |
| 13 Sep 2025 | New Old Stock returns to the Black Duck Cafe Westport CT | Black Duck Cafe, Westport |
| 05 Sep 2025 | September 5th Comedy Night The Westport VFW | Veterans of Foreign Wars, Westport |
| 18 Oct 2025 | Continental Connections | Christ & Holy Trinity Episcopal Church, Westport |
| 12 Aug 2025 | Suzanne Sheridan & Friends at Levitt Pavilion Westport CT | Levitt Pavilion for the Performing Arts, Westport |
| 20 Aug 2025 | Josh Ritter in Westport | The Levitt Pavilion for the Performing Arts, Westport |
| 18 Oct 2025 | Beardsley Gala | The Inn at Longshore, Westport |
| 22 Aug 2025 | John Oates | The Levitt Pavilion for the Performing Arts and Westport Library |
| 20 Aug 2025 | Josh Ritter & The Royal City Band | The Levitt Pavilion for the Performing Arts and Westport Library |
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