Upcoming Events
September 2025
Fri, Sep 19
Kelly McCafferty
The Original Pittsburgh Winery Presents

Kelly McCafferty

Ages 21 and up
Doors: 6 pm // Show: 7 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sep 19
Big Jus & Steeltown Horns
The Original Pittsburgh Winery Presents

Big Jus & Steeltown Horns

Ages 21 and up
Doors: 8 pm // Show: 8 pm
$33.60 / Day Of : $33.6
Pittsburgh Winery
Buy Tickets
More Info
Sat, Sep 20
Heartless Bastards
Drusky Entertainment Presents

Heartless Bastards

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$47.04 / Day Of : $53.48
Pittsburgh Winery
Buy Tickets
More Info
Wed, Sep 24
Luke Winslow-King
The Original Pittsburgh Winery Presents

Luke Winslow-King

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sep 26
Songwriters Night feat. Brooke Annibale, Liz Berlin, & Morgan Erina
The Original Pittsburgh Winery Presents

Songwriters Night feat. Brooke Annibale, Liz Berlin, & Morgan Erina

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sep 26
Bill Henry Band
The Original Pittsburgh Winery Presents

Bill Henry Band

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
Buy Tickets
More Info
Sat, Sep 27
Reuben’s Painted Mandolin – A Tribute to Jerry Garcia Band
The Original Pittsburgh Winery Presents

Reuben’s Painted Mandolin – A Tribute to Jerry Garcia Band

Ages 21 and up
Show: 8 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
Buy Tickets
More Info
October 2025
Wed, Oct 01
The Lightfoot Band: Featuring Original Members of Gordon Lightfoot’s Band
The Original Pittsburgh Winery Presents

The Lightfoot Band: Featuring Original Members of Gordon Lightfoot’s Band

Ages 21 and up
Doors: 6 pm // Show: 7 pm
$53.48 / Day Of : $59.64
Pittsburgh Winery
Buy Tickets
More Info
Sat, Oct 04
TJ Isenberg
The Original Pittsburgh Winery Presents

TJ Isenberg

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Sun, Oct 05
Vocal Confluence: Small Group Showcase
The Original Pittsburgh Winery Presents

Vocal Confluence: Small Group Showcase

Ages 21 and up
Doors: 3 pm // Show: 4 pm
$20.72
Pittsburgh Winery
Buy Tickets
More Info
Fri, Oct 10
Skye Burkett
Just Announced
The Original Pittsburgh Winery Presents

Skye Burkett

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Fri, Oct 10
Gathering Field
The Original Pittsburgh Winery Presents

Gathering Field

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
Buy Tickets
More Info
Sun, Oct 12
Helen Gillet
The Original Pittsburgh Winery Presents

Helen Gillet

Ages 21 and up
Doors: 5 pm // Show: 6 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
Buy Tickets
More Info
Thu, Oct 16
Dizgo & Squeaky Feet
The Original Pittsburgh Winery & Thunderbird Music Hall Present

Dizgo & Squeaky Feet

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
Buy Tickets
More Info
Sat, Oct 18
Pete Hewlett
The Original Pittsburgh Winery Presents

Pete Hewlett

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Sat, Oct 18
Damn Tall Buildings
Calliope Presents

Damn Tall Buildings

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Sun, Oct 19
Kaston Guffey & Georgia English
The Original Pittsburgh Winery Presents

Kaston Guffey & Georgia English

Ages 21 and up
Doors: 12:30 pm // Show: 1:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Wed, Oct 22
Sojourn with Cueva: An Immersive Night of Art & Jazz
Just Announced
Del Caiman Presents

Sojourn with Cueva: An Immersive Night of Art & Jazz

Ages 21 and up
Doors: 5:45 pm // Show: 6:45 pm
$33.02
Pittsburgh Winery
Buy Tickets
More Info
Fri, Oct 24
Whiskey River: A Tribute to Willie Nelson
The Original Pittsburgh Winery Presents

Whiskey River: A Tribute to Willie Nelson

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
Buy Tickets
More Info
Sat, Oct 25
Dress Code
Just Announced
The Original Pittsburgh Winery Presents

Dress Code

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
November 2025
Sat, Nov 01
Songs for Gaza – Fundraising Concert for World Central Kitchen for Gaza Famine
Just Announced
The Original Pittsburgh Winery Presents

Songs for Gaza – Fundraising Concert for World Central Kitchen for Gaza Famine

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88
Pittsburgh Winery
Buy Tickets
More Info
Sun, Nov 02
Steel City Cabaret: The Last Five Years
Steel City Cabaret Presents

Steel City Cabaret: The Last Five Years

Ages 21 and up
Doors: 2:30 pm // Show: 3 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
Buy Tickets
More Info
Sat, Nov 08
Good Brother Earl
Just Announced
The Original Pittsburgh Winery Presents

Good Brother Earl

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
Buy Tickets
More Info
Tue, Nov 11
Joshua Burnside
Drusky Entertainment Presents

Joshua Burnside

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $24.42
Pittsburgh Winery
Buy Tickets
More Info
Thu, Nov 13
The Niche feat. Rob Compa plus special guests Neon Belly
The Original Pittsburgh Winery & Sidequest Present

The Niche feat. Rob Compa plus special guests Neon Belly

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72
Pittsburgh Winery
Buy Tickets
More Info
Fri, Nov 14
Fantastic Cat
91.3 WYEP & Drusky Entertainment Present

Fantastic Cat

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
Pittsburgh Winery
Buy Tickets
More Info
Sat, Nov 15
The Barefoot Movement
Calliope Presents

The Barefoot Movement

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Thu, Nov 20
John Westford
Just Announced
Drusky Entertainment Presents

John Westford

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
Buy Tickets
More Info
Fri, Nov 28
Buzz Poets
Just Announced
The Original Pittsburgh Winery Presents

Buzz Poets

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
Pittsburgh Winery
Buy Tickets
More Info
December 2025
Sat, Dec 06
New Invisible Joy w/ special guests Morgan Erina
Just Announced
The Original Pittsburgh Winery Presents

New Invisible Joy w/ special guests Morgan Erina

Ages 21 and up
Doors: 8 pm // Show: 8 pm
$24.42
Pittsburgh Winery
Buy Tickets
More Info
Sun, Dec 07
Storm Large of Pink Martini: Holiday Ordeal
Just Announced
Drusky Entertainment Presents

Storm Large of Pink Martini: Holiday Ordeal

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$36.29 / Day Of : $40.32
Pittsburgh Winery
Buy Tickets
More Info
Fri, Dec 12
Armchair Boogie
Drusky Entertainment Presents

Armchair Boogie

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
Buy Tickets
More Info
Sat, Dec 13
Lily Henley with Duncan Wickel
Calliope Presents

Lily Henley with Duncan Wickel

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
February 2026
Sat, Feb 28
Jerron Paxton and Dennis Lichtman
Calliope Presents

Jerron Paxton and Dennis Lichtman

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
March 2026
Thu, Mar 12
Hildaland
Calliope Presents

Hildaland

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
April 2026
Sat, Apr 11
Nidia Góngora
Calliope Presents

Nidia Góngora

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
May 2026
Sat, May 09
An Evening with Joy Clark
Calliope Presents

An Evening with Joy Clark

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
Buy Tickets
More Info
Fri, Sep 19
Kelly McCafferty
The Original Pittsburgh Winery Presents

Kelly McCafferty

Ages 21 and up
Doors: 6 pm // Show: 7 pm
$0
Pittsburgh Winery
More Info
Fri, Sep 19
Big Jus & Steeltown Horns
The Original Pittsburgh Winery Presents

Big Jus & Steeltown Horns

Ages 21 and up
Doors: 8 pm // Show: 8 pm
$33.60 / Day Of : $33.6
Pittsburgh Winery
More Info
Sat, Sep 20
Heartless Bastards
Drusky Entertainment Presents

Heartless Bastards

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$47.04 / Day Of : $53.48
Pittsburgh Winery
More Info
Wed, Sep 24
Luke Winslow-King
The Original Pittsburgh Winery Presents

Luke Winslow-King

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
Pittsburgh Winery
More Info
Fri, Sep 26
Songwriters Night feat. Brooke Annibale, Liz Berlin, & Morgan Erina
The Original Pittsburgh Winery Presents

Songwriters Night feat. Brooke Annibale, Liz Berlin, & Morgan Erina

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
More Info
Fri, Sep 26
Bill Henry Band
The Original Pittsburgh Winery Presents

Bill Henry Band

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
More Info
Sat, Sep 27
Reuben’s Painted Mandolin – A Tribute to Jerry Garcia Band
The Original Pittsburgh Winery Presents

Reuben’s Painted Mandolin – A Tribute to Jerry Garcia Band

Ages 21 and up
Show: 8 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
More Info
Wed, Oct 01
The Lightfoot Band: Featuring Original Members of Gordon Lightfoot’s Band
The Original Pittsburgh Winery Presents

The Lightfoot Band: Featuring Original Members of Gordon Lightfoot’s Band

Ages 21 and up
Doors: 6 pm // Show: 7 pm
$53.48 / Day Of : $59.64
Pittsburgh Winery
More Info
Sat, Oct 04
TJ Isenberg
The Original Pittsburgh Winery Presents

TJ Isenberg

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
More Info
Sun, Oct 05
Vocal Confluence: Small Group Showcase
The Original Pittsburgh Winery Presents

Vocal Confluence: Small Group Showcase

Ages 21 and up
Doors: 3 pm // Show: 4 pm
$20.72
Pittsburgh Winery
More Info
Fri, Oct 10
Skye Burkett
Just Announced
The Original Pittsburgh Winery Presents

Skye Burkett

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
More Info
Fri, Oct 10
Gathering Field
The Original Pittsburgh Winery Presents

Gathering Field

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
More Info
Sun, Oct 12
Helen Gillet
The Original Pittsburgh Winery Presents

Helen Gillet

Ages 21 and up
Doors: 5 pm // Show: 6 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
More Info
Thu, Oct 16
Dizgo & Squeaky Feet
The Original Pittsburgh Winery & Thunderbird Music Hall Present

Dizgo & Squeaky Feet

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
More Info
Sat, Oct 18
Pete Hewlett
The Original Pittsburgh Winery Presents

Pete Hewlett

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
More Info
Sat, Oct 18
Damn Tall Buildings
Calliope Presents

Damn Tall Buildings

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
More Info
Sun, Oct 19
Kaston Guffey & Georgia English
The Original Pittsburgh Winery Presents

Kaston Guffey & Georgia English

Ages 21 and up
Doors: 12:30 pm // Show: 1:30 pm
$0
Pittsburgh Winery
More Info
Wed, Oct 22
Sojourn with Cueva: An Immersive Night of Art & Jazz
Just Announced
Del Caiman Presents

Sojourn with Cueva: An Immersive Night of Art & Jazz

Ages 21 and up
Doors: 5:45 pm // Show: 6:45 pm
$33.02
Pittsburgh Winery
More Info
Fri, Oct 24
Whiskey River: A Tribute to Willie Nelson
The Original Pittsburgh Winery Presents

Whiskey River: A Tribute to Willie Nelson

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
More Info
Sat, Oct 25
Dress Code
Just Announced
The Original Pittsburgh Winery Presents

Dress Code

Ages 21 and up
Doors: 4 pm // Show: 5 pm
$0
Pittsburgh Winery
More Info
Sat, Nov 01
Songs for Gaza – Fundraising Concert for World Central Kitchen for Gaza Famine
Just Announced
The Original Pittsburgh Winery Presents

Songs for Gaza – Fundraising Concert for World Central Kitchen for Gaza Famine

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88
Pittsburgh Winery
More Info
Sun, Nov 02
Steel City Cabaret: The Last Five Years
Steel City Cabaret Presents

Steel City Cabaret: The Last Five Years

Ages 21 and up
Doors: 2:30 pm // Show: 3 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
More Info
Sat, Nov 08
Good Brother Earl
Just Announced
The Original Pittsburgh Winery Presents

Good Brother Earl

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
More Info
Tue, Nov 11
Joshua Burnside
Drusky Entertainment Presents

Joshua Burnside

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $24.42
Pittsburgh Winery
More Info
Thu, Nov 13
The Niche feat. Rob Compa plus special guests Neon Belly
The Original Pittsburgh Winery & Sidequest Present

The Niche feat. Rob Compa plus special guests Neon Belly

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72
Pittsburgh Winery
More Info
Fri, Nov 14
Fantastic Cat
91.3 WYEP & Drusky Entertainment Present

Fantastic Cat

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
Pittsburgh Winery
More Info
Sat, Nov 15
The Barefoot Movement
Calliope Presents

The Barefoot Movement

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
More Info
Thu, Nov 20
John Westford
Just Announced
Drusky Entertainment Presents

John Westford

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$26.88 / Day Of : $33.6
Pittsburgh Winery
More Info
Fri, Nov 28
Buzz Poets
Just Announced
The Original Pittsburgh Winery Presents

Buzz Poets

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$33.60 / Day Of : $40.32
Pittsburgh Winery
More Info
Sat, Dec 06
New Invisible Joy w/ special guests Morgan Erina
Just Announced
The Original Pittsburgh Winery Presents

New Invisible Joy w/ special guests Morgan Erina

Ages 21 and up
Doors: 8 pm // Show: 8 pm
$24.42
Pittsburgh Winery
More Info
Sun, Dec 07
Storm Large of Pink Martini: Holiday Ordeal
Just Announced
Drusky Entertainment Presents

Storm Large of Pink Martini: Holiday Ordeal

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$36.29 / Day Of : $40.32
Pittsburgh Winery
More Info
Fri, Dec 12
Armchair Boogie
Drusky Entertainment Presents

Armchair Boogie

Ages 21 and up
Doors: 7 pm // Show: 8 pm
$20.72 / Day Of : $26.88
Pittsburgh Winery
More Info
Sat, Dec 13
Lily Henley with Duncan Wickel
Calliope Presents

Lily Henley with Duncan Wickel

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
More Info
Sat, Feb 28
Jerron Paxton and Dennis Lichtman
Calliope Presents

Jerron Paxton and Dennis Lichtman

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
More Info
Thu, Mar 12
Hildaland
Calliope Presents

Hildaland

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
More Info
Sat, Apr 11
Nidia Góngora
Calliope Presents

Nidia Góngora

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
More Info
Sat, May 09
An Evening with Joy Clark
Calliope Presents

An Evening with Joy Clark

Ages 21 and up
Doors: 6:30 pm // Show: 7:30 pm
$0
Pittsburgh Winery
More Info

VIEW ALL EVENTS

CONTACT

E  |  info@pghwinery.com

T  |  412-566-1000

Contact Us

HOURS

Monday - Tuesday
Closed
Wednesday - Thursday
4PM - 7PM
Friday
4PM - 9PM
Saturday
12PM -8PM
Sunday
12PM - 8PM

VISIT US

2809 Penn Avenue
Pittsburgh, PA 15222

©

2025

PITTSBURGH WINERY

Powered by ROCKHOUSE PARTNERS an ETIX company.

Instagram Facebook Yelp
Skip to content