| Event | Venue | Date/Time | |
| Jill Sobule | City Winery - Pittsburgh
Pittsburgh, PA | Friday
9/5/2025
7:30 PM |  |
| Velvet Hearts Burlesque Brunch | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
9/7/2025
12:00 PM | |
| Jonathan Coulton | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
9/7/2025
7:30 PM | |
| Boozy Bingo | City Winery - Pittsburgh
Pittsburgh, PA | Monday
9/8/2025
7:00 PM | |
| Pitt Floyd - Tribute To Pink Floyd | City Winery - Pittsburgh
Pittsburgh, PA | Wednesday
9/10/2025
7:30 PM | |
| Who's Bad - Michael Jackson Tribute Band | City Winery - Pittsburgh
Pittsburgh, PA | Thursday
9/11/2025
7:30 PM | |
| Charles Esten | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
9/13/2025
7:30 PM | |
| Deja Vu | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
9/14/2025
7:30 PM | |
| Joe Henry & Mike Reid | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
9/16/2025
7:30 PM | |
| Spaga | City Winery - Pittsburgh
Pittsburgh, PA | Wednesday
9/17/2025
7:30 PM | |
| Anthony Rapp | City Winery - Pittsburgh
Pittsburgh, PA | Thursday
9/18/2025
7:30 PM | |
| Lyfe Jennings | City Winery - Pittsburgh
Pittsburgh, PA | Friday
9/19/2025
6:30 PM | |
| Lyfe Jennings | City Winery - Pittsburgh
Pittsburgh, PA | Friday
9/19/2025
9:30 PM | |
| Soul Brunch | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
9/21/2025
12:00 PM | |
| John Violinist | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
9/21/2025
5:30 PM | |
| The Wellermen | City Winery - Pittsburgh
Pittsburgh, PA | Monday
9/22/2025
7:30 PM | |
| Major. | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
9/23/2025
7:30 PM | |
| Chris Jamison | City Winery - Pittsburgh
Pittsburgh, PA | Thursday
9/25/2025
7:30 PM | |
| Steel City Crue - Motley Crue Tribute | City Winery - Pittsburgh
Pittsburgh, PA | Friday
9/26/2025
7:30 PM | |
| Billy Price Band | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
9/27/2025
7:30 PM | |
| Ladies of The 80's Drag Brunch | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
9/28/2025
12:00 PM | |
| Chrisette Michele | City Winery - Pittsburgh
Pittsburgh, PA | Friday
10/3/2025
6:00 PM | |
| Chrisette Michele | City Winery - Pittsburgh
Pittsburgh, PA | Friday
10/3/2025
9:30 PM | |
| Gospel Melodies Day Party & Brunch | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
10/4/2025
12:00 PM | |
| Ami Taf Ra | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
10/5/2025
7:30 PM | |
| Boozy Bingo | City Winery - Pittsburgh
Pittsburgh, PA | Monday
10/6/2025
7:00 PM | |
| Judith Hill | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
10/7/2025
7:30 PM | |
| The Samples | City Winery - Pittsburgh
Pittsburgh, PA | Thursday
10/9/2025
7:30 PM | |
| Think X - An Exploration of the Music of Pink Floyd | City Winery - Pittsburgh
Pittsburgh, PA | Monday
10/13/2025
7:30 PM | |
| My Cousin Tiera | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
10/18/2025
7:30 PM | |
| Lee Ritenour | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
10/19/2025
7:30 PM | |
| Rodney Crowell | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
10/21/2025
7:30 PM | |
| Samantha Bee | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
10/26/2025
8:00 PM | |
| Joshua Radin | City Winery - Pittsburgh
Pittsburgh, PA | Monday
10/27/2025
7:30 PM | |
| Abi Carter | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
10/28/2025
7:30 PM | |
| Cold | City Winery - Pittsburgh
Pittsburgh, PA | Thursday
10/30/2025
7:30 PM | |
| Akron's Real Deal | City Winery - Pittsburgh
Pittsburgh, PA | Friday
10/31/2025
7:30 PM | |
| Freddy Jones Band | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
11/2/2025
7:30 PM | |
| Boozy Bingo | City Winery - Pittsburgh
Pittsburgh, PA | Monday
11/3/2025
7:00 PM | |
| Rob Anderson | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
11/4/2025
7:30 PM | |
| Rob Anderson | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
11/4/2025
9:30 PM | |
| Griffin House | City Winery - Pittsburgh
Pittsburgh, PA | Wednesday
11/5/2025
7:30 PM | |
| John Splithoff | City Winery - Pittsburgh
Pittsburgh, PA | Tuesday
11/11/2025
7:30 PM | |
| Sam Grisman Project | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
11/16/2025
7:30 PM | |
| Alex Skolnick Trio | City Winery - Pittsburgh
Pittsburgh, PA | Monday
11/17/2025
7:30 PM | |
| Boozy Bingo | City Winery - Pittsburgh
Pittsburgh, PA | Monday
12/1/2025
7:00 PM | |
| The Empty Pockets | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
12/7/2025
7:30 PM | |
| Mary Fahl | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
12/14/2025
7:30 PM | |
| Justin Fabus | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
1/10/2026
7:30 PM | |
| The Seven Wonders - Fleetwood Mac Tribute | City Winery - Pittsburgh
Pittsburgh, PA | Saturday
1/31/2026
7:30 PM | |
| The Seven Wonders - Fleetwood Mac Tribute Brunch | City Winery - Pittsburgh
Pittsburgh, PA | Sunday
2/1/2026
12:00 PM | |
