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