| Martin Sexton | 3-13-2026
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Kim Gordon's Black And Red Masquerade Ball | 3-14-2026
Saturday
7:30 PM | Key West Theater in Key West, FL | View Tickets |
| Tommy Emmanuel | 3-22-2026
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Bumpin' Uglies | 3-25-2026
Wednesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| The '77 Experience | 3-28-2026
Saturday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| BoDeans | 3-29-2026
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Squirrel Nut Zippers | 4-2-2026
Thursday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Crystal Gayle | 4-7-2026
Tuesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Donavon Frankenreiter | 4-12-2026
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Graham Nash | 4-25-2026
Saturday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Graham Nash | 4-26-2026
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| 10,000 Maniacs | 5-10-2026
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Steve Earle | 6-9-2026
Tuesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Rum Fest: Cliff Cody & Sharese | 8-14-2026
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Garrison Keillor & Erica Rhodes | 10-27-2026
Tuesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Bruce Cockburn & Livingston Taylor | 11-8-2026
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Marty Stuart and His Fabulous Superlatives | 11-19-2026
Thursday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Dusty Slay | 11-20-2026
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Dusty Slay | 11-21-2026
Saturday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
