| 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 |
| A Classic Holiday | 12-17-2025
Wednesday
7:30 AM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Pleaktunes Trio: A Charlie Brown Christmas Album Live | 12-19-2025
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Brownie Mary's Kelsey & Co. | 12-26-2025
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Reuben's Painted Mandolin - Jerry Garcia Band Tribute | 12-27-2025
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Letizia Collini & Grace Elliott | 12-28-2025
Sunday
7:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Steeltown Horns Band | 12-31-2025
Wednesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Woodland Creatures | 1-10-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Jim Krenn | 1-16-2026
Friday
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 |
| Donora | 1-23-2026
Friday
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 |
| Makaya McCraven | 2-19-2026
Thursday
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 |
| Hildaland | 3-12-2026
Thursday
7:30 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 |
| 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 |
