| Joshua Burnside | 11-11-2025
Tuesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| The Niche | 11-13-2025
Thursday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Fantastic Cat | 11-14-2025
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| The Barefoot Movement | 11-15-2025
Saturday
7:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| John Westford | 11-21-2025
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Buzz Poets | 11-28-2025
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| New Invisible Joy | 12-6-2025
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| The Storm Large Holiday Ordeal | 12-7-2025
Sunday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Armchair Boogie | 12-12-2025
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Lily Henley | 12-13-2025
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Stephen Kellogg and The Homecoming | 1-20-2026
Tuesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Mike Dawes | 2-7-2026
Saturday
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 |
| Hildaland | 3-12-2026
Thursday
7:30 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 |
| An Evening with Joy Clark | 5-9-2026
Saturday
7:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
