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Just Announced
July 2024
Sat, July 27
Drusky Entertainment Presents
Jim Messina
Ages 21 and up
Doors: 7pm // Show: 8pm
$60
Pittsburgh Winery
Buy Tickets
More Info
Wed, July 31
The Original Pittsburgh Winery Presents
Kommuna Lux
Ages 21 and up
Doors: 7pm // Show: 8pm
$25 / Day Of : $30
Pittsburgh Winery
Buy Tickets
More Info
August 2024
Thu, Aug 01
The Original Pittsburgh Winery Presents
Jeremy Pinnell w/ special guest John Bindley
Ages 21 and up
Doors: 7pm // Show: 8pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Fri, Aug 02
The Original Pittsburgh Winery Presents
Clunkers & Friends w/ special guests Thrown Out Bones
Ages 21 and up
Doors: 8pm // Show: 8pm
$20 / Day Of : $25
Pittsburgh Winery
Buy Tickets
More Info
Sat, Aug 03
Just Announced
Don't Tell Comedy Presents
Don’t Tell Pittsburgh (Strip District)
Ages 21 and up
Doors: 8pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
Sun, Aug 04
The Original Pittsburgh Winery Presents
Taylor Kelly w/ Inez and Back Alley Sound
Ages 21 and up
Doors: 6pm // Show: 7pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Thu, Aug 08
Drusky Entertainment Presents
Rebirth Brass Band
Ages 21 and up
Doors: 7pm // Show: 8pm
$20
Pittsburgh Winery
Buy Tickets
More Info
Fri, Aug 09
The Original Pittsburgh Winery Presents
Reuben’s Painted Mandolin – The Days Between Closeout Celebration
Ages 21 and up
Doors: 7pm // Show: 8pm
$10 / Day Of : $15
Pittsburgh Winery
Buy Tickets
More Info
Sat, Aug 10
The Original Pittsburgh Winery Presents
Cisco Kid w/ The Buckle Downs & Timbeleza
Ages 21 and up
Doors: 7pm // Show: 8pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Fri, Aug 16
Just Announced
The Original Pittsburgh Winery Presents
Ross Heastings – 5 Stages of Grief w/ special guest Danny Rectenwald
Ages 21 and up
Doors: 7pm // Show: 8pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Sat, Aug 17
Just Announced
The Original Pittsburgh Winery Presents
Leila Rhodes ‘Still Dreaming’ EP Release
Ages 21 and up
Doors: 6pm // Show: 7pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Sun, Aug 25
Drusky Entertainment Presents
Emily Wolfe
Ages 21 and up
Doors: 7pm // Show: 7pm
$15
Pittsburgh Winery
Buy Tickets
More Info
September 2024
Tue, Sept 10
Drusky Entertainment Presents
Ghost Note
Ages 21 and up
Doors: 8pm // Show: 8pm
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sept 13
Drusky Entertainment Presents
Veronica Swift
Ages 21 and up
Doors: 7pm // Show: 8pm
$32
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sept 20
Calliope Presents
An Intimate Evening with Victor Wainwright & Friends
Ages 21 and up
Doors: 7:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
Sun, Sept 22
Just Announced
The Original Pittsburgh Winery Presents
Charming Disaster w/ Take Me With You
Ages 21 and up
Doors: 2:30pm // Show: 3:30pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Sun, Sept 22
Vocal Confluence Presents
Small Group Showcase
Ages 21 and up
Doors: 3pm // Show: 4pm
$20 / Day Of : $25
Pittsburgh Winery
Buy Tickets
More Info
Wed, Sept 25
Drusky Entertainment Presents
Colin James
Ages 21 and up
Doors: 7pm // Show: 7pm
$20
Pittsburgh Winery
Buy Tickets
More Info
Mon, Sept 30
Drusky Entertainment Presents
The Georgia Thunderbolts
Ages 21 and up
Doors: 8pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
October 2024
Sun, Oct 06
The Original Pittsburgh Winery Presents
91.3 WYEP Presents: Tom Paxton & Buffalo Rose
Ages 21 and up
Doors: 7pm // Show: 7pm
$35 / Day Of : $40
Pittsburgh Winery
Buy Tickets
More Info
Sat, Oct 19
The Original Pittsburgh Winery Presents
Noah Gundersen w/ Abby Gundersen: Ledges 10 Year Anniversary
Ages 21 and up
Doors: 7pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
Fri, Oct 25
Calliope Presents
Tray Wellington Band
Ages 21 and up
Doors: 6:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
November 2024
Sat, Nov 09
Drusky Entertainment Presents
Billy Prine Presents The Songs of John Prine
Ages 21 and up
Doors: 6:30pm // Show: 6:30pm
$30
Pittsburgh Winery
Buy Tickets
More Info
Wed, Nov 13
Drusky Entertainment Presents
Ronnie Baker Brooks
Ages 21 and up
Doors: 8pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
Fri, Nov 15
Calliope Presents
Alison Brown
Ages 21 and up
Doors: 7:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
Sat, Nov 16
Just Announced
Drusky Entertainment Presents
Wild Pink & John Francis Flynn
Ages 21 and up
Doors: 7pm // Show: 8pm
$15
Pittsburgh Winery
Buy Tickets
More Info
March 2025
Fri, Mar 21
Calliope Presents
J2B2 (John Jorgenson Bluegrass Band)
Ages 21 and up
Doors: 6:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
April 2025
Fri, Apr 25
Calliope Presents
Gabby Moreno
Ages 21 and up
Doors: 6:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
Sat, July 27
Drusky Entertainment Presents
Jim Messina
Ages 21 and up
Doors: 7pm // Show: 8pm
$60
Pittsburgh Winery
Buy Tickets
More Info
Wed, July 31
The Original Pittsburgh Winery Presents
Kommuna Lux
Ages 21 and up
Doors: 7pm // Show: 8pm
$25 / Day Of : $30
Pittsburgh Winery
Buy Tickets
More Info
Thu, Aug 01
The Original Pittsburgh Winery Presents
Jeremy Pinnell w/ special guest John Bindley
Ages 21 and up
Doors: 7pm // Show: 8pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Fri, Aug 02
The Original Pittsburgh Winery Presents
Clunkers & Friends w/ special guests Thrown Out Bones
Ages 21 and up
Doors: 8pm // Show: 8pm
$20 / Day Of : $25
Pittsburgh Winery
Buy Tickets
More Info
Sat, Aug 03
Just Announced
Don't Tell Comedy Presents
Don’t Tell Pittsburgh (Strip District)
Ages 21 and up
Doors: 8pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
Sun, Aug 04
The Original Pittsburgh Winery Presents
Taylor Kelly w/ Inez and Back Alley Sound
Ages 21 and up
Doors: 6pm // Show: 7pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Thu, Aug 08
Drusky Entertainment Presents
Rebirth Brass Band
Ages 21 and up
Doors: 7pm // Show: 8pm
$20
Pittsburgh Winery
Buy Tickets
More Info
Fri, Aug 09
The Original Pittsburgh Winery Presents
Reuben’s Painted Mandolin – The Days Between Closeout Celebration
Ages 21 and up
Doors: 7pm // Show: 8pm
$10 / Day Of : $15
Pittsburgh Winery
Buy Tickets
More Info
Sat, Aug 10
The Original Pittsburgh Winery Presents
Cisco Kid w/ The Buckle Downs & Timbeleza
Ages 21 and up
Doors: 7pm // Show: 8pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Fri, Aug 16
Just Announced
The Original Pittsburgh Winery Presents
Ross Heastings – 5 Stages of Grief w/ special guest Danny Rectenwald
Ages 21 and up
Doors: 7pm // Show: 8pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Sat, Aug 17
Just Announced
The Original Pittsburgh Winery Presents
Leila Rhodes ‘Still Dreaming’ EP Release
Ages 21 and up
Doors: 6pm // Show: 7pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Sun, Aug 25
Drusky Entertainment Presents
Emily Wolfe
Ages 21 and up
Doors: 7pm // Show: 7pm
$15
Pittsburgh Winery
Buy Tickets
More Info
Tue, Sept 10
Drusky Entertainment Presents
Ghost Note
Ages 21 and up
Doors: 8pm // Show: 8pm
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sept 13
Drusky Entertainment Presents
Veronica Swift
Ages 21 and up
Doors: 7pm // Show: 8pm
$32
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sept 20
Calliope Presents
An Intimate Evening with Victor Wainwright & Friends
Ages 21 and up
Doors: 7:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
Sun, Sept 22
Just Announced
The Original Pittsburgh Winery Presents
Charming Disaster w/ Take Me With You
Ages 21 and up
Doors: 2:30pm // Show: 3:30pm
$15 / Day Of : $20
Pittsburgh Winery
Buy Tickets
More Info
Sun, Sept 22
Vocal Confluence Presents
Small Group Showcase
Ages 21 and up
Doors: 3pm // Show: 4pm
$20 / Day Of : $25
Pittsburgh Winery
Buy Tickets
More Info
Wed, Sept 25
Drusky Entertainment Presents
Colin James
Ages 21 and up
Doors: 7pm // Show: 7pm
$20
Pittsburgh Winery
Buy Tickets
More Info
Mon, Sept 30
Drusky Entertainment Presents
The Georgia Thunderbolts
Ages 21 and up
Doors: 8pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
Sun, Oct 06
The Original Pittsburgh Winery Presents
91.3 WYEP Presents: Tom Paxton & Buffalo Rose
Ages 21 and up
Doors: 7pm // Show: 7pm
$35 / Day Of : $40
Pittsburgh Winery
Buy Tickets
More Info
Sat, Oct 19
The Original Pittsburgh Winery Presents
Noah Gundersen w/ Abby Gundersen: Ledges 10 Year Anniversary
Ages 21 and up
Doors: 7pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
Fri, Oct 25
Calliope Presents
Tray Wellington Band
Ages 21 and up
Doors: 6:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
Sat, Nov 09
Drusky Entertainment Presents
Billy Prine Presents The Songs of John Prine
Ages 21 and up
Doors: 6:30pm // Show: 6:30pm
$30
Pittsburgh Winery
Buy Tickets
More Info
Wed, Nov 13
Drusky Entertainment Presents
Ronnie Baker Brooks
Ages 21 and up
Doors: 8pm // Show: 8pm
$25
Pittsburgh Winery
Buy Tickets
More Info
Fri, Nov 15
Calliope Presents
Alison Brown
Ages 21 and up
Doors: 7:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
Sat, Nov 16
Just Announced
Drusky Entertainment Presents
Wild Pink & John Francis Flynn
Ages 21 and up
Doors: 7pm // Show: 8pm
$15
Pittsburgh Winery
Buy Tickets
More Info
Fri, Mar 21
Calliope Presents
J2B2 (John Jorgenson Bluegrass Band)
Ages 21 and up
Doors: 6:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
Fri, Apr 25
Calliope Presents
Gabby Moreno
Ages 21 and up
Doors: 6:30pm // Show: 7:30pm
$45
Pittsburgh Winery
Buy Tickets
More Info
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