| Jill Sobule | 9-5-2025
Friday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Velvet Hearts Burlesque Brunch | 9-7-2025
Sunday
12:00 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 |
| Joe Henry & Mike Reid | 9-16-2025
Tuesday
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 |
| Soul Brunch | 9-21-2025
Sunday
12:00 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 |
| Major. | 9-23-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Chris Jamison | 9-25-2025
Thursday
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 |
| Ladies of The 80's Drag Brunch | 9-28-2025
Sunday
12:00 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 |
| Gospel Melodies Day Party & Brunch | 10-4-2025
Saturday
12:00 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 |
| Judith Hill | 10-7-2025
Tuesday
7:30 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 |
| 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 |
| Cold | 10-30-2025
Thursday
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 |
| Freddy Jones Band | 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 |
| John Splithoff | 11-11-2025
Tuesday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Sam Grisman Project | 11-16-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Alex Skolnick Trio | 11-17-2025
Monday
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 |
| The Empty Pockets | 12-7-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Mary Fahl | 12-14-2025
Sunday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| Justin Fabus | 1-10-2026
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Seven Wonders - Fleetwood Mac Tribute | 1-31-2026
Saturday
7:30 PM | City Winery in Pittsburgh, PA | View Tickets |
| The Seven Wonders - Fleetwood Mac Tribute Brunch | 2-1-2026
Sunday
12:00 PM | City Winery in Pittsburgh, PA | View Tickets |
