| Change of Heart - Tom Petty Tribute | 11-13-2026 Friday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Mamma Mia! An Abbafabulous Brunch | 11-14-2026 Saturday 12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Joshua Radin | 11-14-2026 Saturday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| PureSoul - A Tribute to Sade | 11-15-2026 Sunday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Marcus Veltri & Rob Landes | 11-18-2026 Wednesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Q Parker | 11-19-2026 Thursday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Beatles Tribute Brunch | 11-21-2026 Saturday 12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Dolly Parton Drag Show | 11-21-2026 Saturday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Walls Group | 11-22-2026 Sunday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Latrice Royale | 11-23-2026 Monday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Cassadee Pope | 11-24-2026 Tuesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Prince Experience - Prince Tribute | 11-27-2026 Friday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Lola LeCroix Drag Brunch | 11-29-2026 Sunday 12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Christopher Williams | 11-29-2026 Sunday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Boozy Trivia Bingo With Kat De Lac | 11-30-2026 Monday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Shep Rose | 12-1-2026 Tuesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| O-Town | 12-2-2026 Wednesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Shep Rose | 12-4-2026 Friday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Christmas with Over The Rhine | 12-7-2026 Monday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Mickey Guyton | 12-8-2026 Tuesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Shep Rose | 12-13-2026 Sunday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| An Irish Christmas: John Doyle, Cathie Ryan & Mick McAuley | 12-14-2026 Monday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Jon McLaughlin | 12-15-2026 Tuesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Bad Plus | 12-16-2026 Wednesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Michael Bublé Tribute Show | 12-17-2026 Thursday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| A Pure Soul Christmas | 12-19-2026 Saturday 12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Morgan James | 12-19-2026 Saturday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| L.A. Young's Phyllis Hyman Tribute Brunch | 12-20-2026 Sunday 12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Adam Brock | 12-21-2026 Monday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Jody Nardone Trio | 12-22-2026 Tuesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Musiq Soulchild | 12-27-2026 Sunday 6:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Musiq Soulchild | 12-27-2026 Sunday 9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Musiq Soulchild | 12-28-2026 Monday 6:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Musiq Soulchild | 12-28-2026 Monday 9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Musiq Soulchild | 12-30-2026 Wednesday 6:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Musiq Soulchild | 12-30-2026 Wednesday 9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Let's Groove Tonight - Earth, Wind and Fire Tribute | 1-1-2027 Friday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Seven Wonders - Fleetwood Mac Tribute | 1-8-2027 Friday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Seven Wonders - Fleetwood Mac Tribute | 1-9-2027 Saturday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Dancing Machine Brunch | 1-10-2027 Sunday 12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Chaunte Wayans | 1-10-2027 Sunday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Andy Falco & Travis Book | 1-14-2027 Thursday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Raheem DeVaughn | 1-15-2027 Friday 6:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Raheem DeVaughn | 1-15-2027 Friday 9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Josh Blue | 1-16-2027 Saturday 6:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Josh Blue | 1-16-2027 Saturday 9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Chrisette Michele | 1-17-2027 Sunday 5:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Chrisette Michele | 1-17-2027 Sunday 8:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Smilo and The Ghost | 1-20-2027 Wednesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Cris Jacobs | 1-24-2027 Sunday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Gabe Dixon | 1-26-2027 Tuesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Yacht Rocket | 1-27-2027 Wednesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Rob Anderson | 1-29-2027 Friday 6:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Anthony Varela | 2-4-2027 Thursday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Amber Wallin | 2-13-2027 Saturday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Gabriella Lester | 2-19-2027 Friday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| On The Lash | 3-4-2027 Thursday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Clay Aiken | 3-7-2027 Sunday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Nick Heyward | 3-9-2027 Tuesday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Valerie June | 3-19-2027 Friday 6:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Valerie June | 3-19-2027 Friday 9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Basketmouth | 4-8-2027 Thursday 7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Jason Ladanye | 4-11-2027 Sunday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Jorma Kaukonen | 5-2-2027 Sunday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Martin Sexton | 5-16-2027 Sunday 7:00 PM | City Winery in Pittsburgh, PA | View Tickets |