| Three Kings | 1-30-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Brave The Sea | 2-5-2026
Thursday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Bob Marley Earthstrong Celebration | 2-6-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Brown Sugar Voodoo - D'Angelo Tribute | 2-13-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Makaya McCraven | 2-19-2026
Thursday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Lyndsey Smith | 2-20-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Garcia Grisman Revue | 2-21-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Elise Trouw | 2-25-2026
Wednesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Driftwood | 2-27-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Jerron Paxton | 2-28-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Gathering Field | 3-6-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Hildaland | 3-12-2026
Thursday
7:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Mark Dignam | 3-13-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Sun King Warriors - Band | 3-14-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| The Town Pants | 3-20-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Rebirth Brass Band | 3-25-2026
Wednesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Todd Barry | 4-4-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Chris Knight | 4-9-2026
Thursday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Nidia Gongora | 4-11-2026
Saturday
7:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Yasmin Williams | 4-14-2026
Tuesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Colin James, Matt Anderson & Terra Lightfoot | 5-2-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| An Evening with Joy Clark | 5-9-2026
Saturday
7:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| David Cross | 5-16-2026
Saturday
9:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Larry McCray | 7-17-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
