| The Holy Gift - Tribute to Tool | 5-22-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Reuben's Painted Mandolin - Jerry Garcia Band Tribute | 5-23-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Songwriters Sunday | 5-24-2026
Sunday
1:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Standup In The Cellar | 5-30-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Flamenco Pittsburgh: Duende - A Student's Journey | 5-31-2026
Sunday
5:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Floyd Mercantile | 6-4-2026
Thursday
7:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Vincen Garcia | 6-6-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Billy Allen & The Pollies | 6-7-2026
Sunday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| The Clunkers | 6-12-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Kevin Nealon | 6-19-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Kevin Nealon | 6-20-2026
Saturday
7:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Kevin Nealon | 6-20-2026
Saturday
9:30 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Brownie Mary's Kelsey & Co. | 6-26-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Sierra Sellers | 7-3-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| The Deslondes | 7-7-2026
Tuesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| East Nash Grass | 7-11-2026
Saturday
8:00 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 |
| Buzz Poets | 8-7-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Chet Vincent | 9-5-2026
Saturday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Aaron Rowe | 9-18-2026
Friday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
| Mike Dawes | 10-21-2026
Wednesday
8:00 PM | The Original Pittsburgh Winery in Pittsburgh, PA | View Tickets |
