The Original Pittsburgh Winery events

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Fri Jun 26 8:00pm
Brownie Mary's Kelsey & Co.
The Original Pittsburgh Winery  •  Pittsburgh, PA
Fri Jul 3 8:00pm
Sierra Sellers
The Original Pittsburgh Winery  •  Pittsburgh, PA
Tue Jul 7 8:00pm
The Deslondes
The Original Pittsburgh Winery  •  Pittsburgh, PA
Sat Jul 11 8:00pm
East Nash Grass
The Original Pittsburgh Winery  •  Pittsburgh, PA
Fri Jul 17 8:00pm
Larry McCray
The Original Pittsburgh Winery  •  Pittsburgh, PA
Fri Aug 7 8:00pm
Buzz Poets
The Original Pittsburgh Winery  •  Pittsburgh, PA
Sat Sep 5 8:00pm
Chet Vincent
The Original Pittsburgh Winery  •  Pittsburgh, PA
Fri Sep 18 8:00pm
Aaron Rowe
The Original Pittsburgh Winery  •  Pittsburgh, PA
Wed Oct 21 8:00pm
Mike Dawes
The Original Pittsburgh Winery  •  Pittsburgh, PA




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The Original Pittsburgh Winery tickets & upcoming events

The Original Pittsburgh Winery is a standout location for events in Pittsburgh. We offer a complete guide to upcoming concerts, including The Original Pittsburgh Winery tickets, seating charts, parking details, and an interactive event calendar for Pittsburgh, PA. Looking for a chill spot to enjoy some good wine and even better vibes? The Original Pittsburgh Winery is where you want to be. It’s not just about the vino, though their wine is pretty fantastic, it’s the whole cozy, eco-friendly scene. As you walk in, you’re greeted by natural wood finishes and lush green plants that somehow make you feel right at home. They’ve got this cool lighting setup that sets a relaxed mood, especially when the sun dips down. The staff? Super friendly and knowledgeable, with sommeliers who actually want to chat about the wines and help you find your new favorite. Bonus points for thoughtful touches like hooks under the bar seats so you can hang your bag or purse, and high tops perfect for standing and sipping if you’re not feeling sitting down. Getting there’s a breeze too, just walk from the bed and breakfast past the clock tower or head east on commerce road from the mall and you’ll spot it easily. Honestly, it’s a little gem that makes you want to stay longer than you planned, whether you’re just grabbing a glass or catching a live concert. And talking about shows, yeah, they support local artists and host live events that totally elevate the experience. So, whether you’re a wine lover or just looking for a fun night out, The Original Pittsburgh Winery is a great choice, trust me, you’ll leave with a smile and maybe a new favorite wine in hand.

Parking & Directions for The Original Pittsburgh Winery


2815 Penn Ave, Pittsburgh, PA
15222, US


1. Street parking - 0.1 miles - Free
2. Lot at 400 S. 7th St. - 0.2 miles - $5
3. Lot at 1500 S. 12th St. - 0.3 miles - $6
4. Parking garage at 101 S. 7th St. - 0.4 miles - $8
5. Lot at 1100 S. 12th St. - 0.5 miles - $5

The Original Pittsburgh Winery concerts - 2026 event schedule highlights in Pittsburgh

The Original Pittsburgh Winery is a vibrant venue hosting a diverse lineup of live performances and events throughout the year. Fans can enjoy comedy shows, musical performances, and cultural celebrations in an intimate setting. Notable upcoming events include stand-up comedy by Kevin Nealon on june 19 and 20, 2026, with three performances scheduled over the weekend. Music lovers can look forward to shows such as Mike Dawes on october 21, 2026, and The Deslondes on july 7, 2026. Other highlighted performances feature East Nash Grass on July 11, 2026, and Larry McCray on July 17, 2026, offering a rich variety of genres. The venue will also host performances by Vittorio Angelone on may 29, 2026, Vincen Garcia on June 6, 2026, and Buzz Poets on august 7, 2026. Additionally, there are special events like 'Standup In The Cellar' on May 30, 2026, and 'Flamenco Pittsburgh: Duende - A Student's Journey' on May 31, 2026, celebrating arts and culture. Other musical acts include Sierra Sellers on July 3, 2026, Chet Vincent on september 5, 2026, and Aaron Rowe on September 18, 2026. The venue also features recurring performances such as Brownie Mary's Kelsey & Co. on June 26, 2026. With a calendar packed with diverse entertainment, The Original Pittsburgh Winery continues to be a premier destination for live performances in Pittsburgh, PA.