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Just Announced
April 2026
Sat, Apr 18
The Original Pittsburgh Winery Presents
Drag Brunch with Jasmine Kennedie (RuPaul’s Drag Race), Aurora Gozmic (Dragula), & Pi (Dragula)
Ages 21 and up
Doors: 11 am // Show: 12 pm
$26.88 / Day Of : $33.6
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Sat, Apr 18
Just Announced
The Original Pittsburgh Winery Presents
Jeff Taylor & Rich Cahill
Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
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Sat, Apr 18
The Original Pittsburgh Winery & The Parking Pad Present
Organ Fairchild w/ Barnacle Feet
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
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Sun, Apr 19
Just Announced
The Original Pittsburgh Winery Presents
Songwriters Sunday: Cody Piper | Ursula Hansberry | Katelyn Fajardo
Ages 21 and up
Doors: 12:30 pm // Show: 1:30 pm
$14.56 / Day Of : $20.72
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Wed, Apr 22
Just Announced
The Original Pittsburgh Winery Presents
Jimbo Jackson & Jason Caliguri
Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
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Thu, Apr 23
Just Announced
The Original Pittsburgh Winery Presents
Trinity Wiseman
Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
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Fri, Apr 24
Just Announced
The Original Pittsburgh Winery Presents
Joey Papadakos
Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
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Fri, Apr 24
The Original Pittsburgh Winery Presents
theCAUSE ‘Steel Your Face’ w/ special guest Randy Baumann
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
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Sat, Apr 25
Just Announced
High Pressure Sound Presents
Roots Sessions
Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
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Sat, Apr 25
The Original Pittsburgh Winery Presents
SamJAMwich
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
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Sun, Apr 26
Just Announced
The Original Pittsburgh Winery Presents
Dress Code
Ages 21 and up
Doors: 12:30 pm // Show: 1:30 pm
$0
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Sun, Apr 26
Flamenco Pittsburgh Presents
Duende: A Flamenco Journey
Ages 21 and up
Doors: 6 pm // Show: 6:30 pm
$18.49 to $33.60 / Day Of : $47.04
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May 2026
Fri, May 01
Just Announced
The Original Pittsburgh Winery Presents
Walk on Mars w/ American Vanity, Danny Goo, & Candice Lee
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
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Sat, May 02
Drusky Entertainment Presents
The Coast to Coast Tour: Colin James, Matt Andersen, & Terra Lightfoot
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$40.32 / Day Of : $47.04
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Fri, May 08
The Original Pittsburgh Winery Presents
Mike Minda’s Be Free
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
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Sat, May 09
Calliope Presents
An Evening with Joy Clark
Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$59.64
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Thu, May 14
The Original Pittsburgh Winery Presents
Big Shrimp w/ Neon Belly
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
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Fri, May 15
The Original Pittsburgh Winery Presents
David Cross: Shootin’ The Shit, Seeing What Sticks
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$47.04
SOLD OUT
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Sat, May 16
The Original Pittsburgh Winery Presents
David Cross: Shootin’ The Shit, Seeing What Sticks
Ages 21 and up
Doors: 6 pm // Show: 7 pm
$47.04
SOLD OUT
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Sat, May 16
The Original Pittsburgh Winery Presents
David Cross: Shootin’ The Shit, Seeing What Sticks
Ages 21 and up
Doors: 8:30 pm // Show: 9:30 pm
$47.04
SOLD OUT
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Fri, May 22
Just Announced
The Original Pittsburgh Winery Presents
The Holy Gift: A Tribute to Tool w/ special guests Shattered
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
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Sun, May 24
Just Announced
The Original Pittsburgh Winery Presents
Songwriters Sunday: Zoob, Sadie Friend, & Xander Hendrickson
Ages 21 and up
Doors: 12:30 pm // Show: 1:30 pm
$14.56 / Day Of : $20.72
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June 2026
Thu, Jun 04
The Original Pittsburgh Winery Presents
Floyd Mercantile
Ages 21 and up
Doors: 6 pm // Show: 7 pm
$34.17 / Day Of : $40.89
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Sat, Jun 06
Just Announced
The Original Pittsburgh Winery & Drusky Entertainment Present
Vincen GarcÃa
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
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Sun, Jun 07
Just Announced
Drusky Entertainment Presents
Billy Allen + The Pollies
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
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Fri, Jun 19
Bottlerocket & The Original Pittsburgh Winery Present
Kevin Nealon
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$59.64
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Sat, Jun 20
Bottlerocket & The Original Pittsburgh Winery Present
Kevin Nealon
Ages 21 and up
Doors: 6 pm // Show: 7 pm
$59.64
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Sat, Jun 20
Bottlerocket & The Original Pittsburgh Winery Present
Kevin Nealon
Ages 21 and up
Doors: 8:30 pm // Show: 9:30 pm
$59.64
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July 2026
Sat, Jul 11
Just Announced
The Original Pittsburgh Winery & Drusky Entertainment Present
East Nash Grass
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
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Fri, Jul 17
Drusky Entertainment Presents
Larry McCray
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$36.96 / Day Of : $47.04
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August 2026
Fri, Aug 07
The Original Pittsburgh Winery Presents
Buzz Poets w/ special guests Latecomer & Anthony Vincent Jardine
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
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September 2026
Fri, Sep 18
Just Announced
Drusky Entertainment Presents
Aaron Rowe
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
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October 2026
Wed, Oct 21
Drusky Entertainment Presents
Mike Dawes
Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
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