| AJ Ghent | 7-19-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Abe Partridge & Jack Barksdale | 7-22-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Let's Sing Taylor - A Live Band Celebrating Music of Taylor Swift | 7-23-2025
Wednesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| 7Horse | 7-24-2025
Thursday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Back and Forth - Foo Fighters Tribute | 7-25-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| City Winery Brunch Series: A Tribute to Fela Kuti, Bob Marley & AfroBeats | 7-26-2025
Saturday
12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Joe Grushecky and The Houserockers | 7-26-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Honky Tonk Brunch | 7-27-2025
Sunday
12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Lithium - Nirvana Tribute Band | 7-27-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Wheel of Drag | 7-28-2025
Monday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Scheana Shay | 7-29-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Shanice | 7-30-2025
Wednesday
6:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Goapele | 7-31-2025
Thursday
5:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Goapele | 7-31-2025
Thursday
8:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Caligula Blushed | 8-1-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Dead Letter Office - A Tribute To R.E.M. | 8-2-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| From London With Love - Tribute to Amy Winehouse & Adele | 8-3-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Boozy Bingo | 8-4-2025
Monday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Tracy Bonham & Jeffrey Gaines | 8-5-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Still Feel Like Your Band - A Tribute To John Mayer | 8-7-2025
Thursday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Prince Experience - Prince Tribute | 8-8-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The 30+ Party | 8-9-2025
Saturday
6:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Comedy & Song with Loni Love | 8-10-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Hip Hop and R&B Bingo With Tom Swoope | 8-11-2025
Monday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Christi Show: Ms. Shirleen | 8-14-2025
Thursday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Damon Darling | 8-16-2025
Saturday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Elle Varner | 8-17-2025
Sunday
5:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Elle Varner | 8-17-2025
Sunday
8:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Drag Race Tuesday Trivia Night | 8-19-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Crandall Creek | 8-22-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Pitt Floyd Brunch | 8-23-2025
Saturday
12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| B5 | 8-23-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Syleena Johnson | 8-24-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Stone Cold and The Jackal | 8-28-2025
Thursday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Ari Shapiro | 8-29-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Billy Price Band | 8-30-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Jill Sobule | 9-5-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Jonathan Coulton | 9-7-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Boozy Bingo | 9-8-2025
Monday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Pitt Floyd - Tribute To Pink Floyd | 9-10-2025
Wednesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Who's Bad - Michael Jackson Tribute Band | 9-11-2025
Thursday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Charles Esten | 9-13-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Deja Vu | 9-14-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Spaga | 9-17-2025
Wednesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Anthony Rapp | 9-18-2025
Thursday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Lyfe Jennings | 9-19-2025
Friday
6:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Lyfe Jennings | 9-19-2025
Friday
9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| John Violinist | 9-21-2025
Sunday
5:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Wellermen | 9-22-2025
Monday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Steel City Crue - Motley Crue Tribute | 9-26-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Billy Price Band | 9-27-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Chrisette Michele | 10-3-2025
Friday
6:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Chrisette Michele | 10-3-2025
Friday
9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Ami Taf Ra | 10-5-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Boozy Bingo | 10-6-2025
Monday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Samples | 10-9-2025
Thursday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Think X - An Exploration of the Music of Pink Floyd | 10-13-2025
Monday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Emily Ann Roberts | 10-16-2025
Thursday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| My Cousin Tiera | 10-18-2025
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Lee Ritenour | 10-19-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Rodney Crowell | 10-21-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Samantha Bee | 10-26-2025
Sunday
8:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Joshua Radin | 10-27-2025
Monday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Abi Carter | 10-28-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Akron's Real Deal | 10-31-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Mary Fahl | 11-2-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Boozy Bingo | 11-3-2025
Monday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
| Rob Anderson | 11-4-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Rob Anderson | 11-4-2025
Tuesday
9:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Griffin House | 11-5-2025
Wednesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Boozy Bingo | 12-1-2025
Monday
7:00 PM | City Winery in Pittsburgh, PA | View Tickets |
