The Original Pittsburgh Winery events

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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. If you're looking to experience a little slice of Pittsburgh history with a splash of wine, The Original Pittsburgh Winery is where you wanna be. It’s actually the first spot in the city to offer a 'Wine and History' tour, yeah, you get to sip and learn about the city's rich past all in one go. The staff? Total pros, including some seriously knowledgeable sommeliers who make the tasting feel like hanging out with friends. Back in 2018, the winery even made it onto a nationwide travel series highlighting Pittsburgh’s amazing food scene, pretty cool, right? And get this, in 2026 they rolled out a new line of biodynamic wines, responding to folks who are into eco-friendly choices. The community table? That's where the magic happens, guests often end up swapping stories and making new friends over shared pours. For those looking for a little luxury, their VIP area offers a cozy, secluded spot with premium tastings. Plus, it’s a breeze to get there, just a short walk from the streetcar stop, and if you're coming from the east, the main avenue leads straight to the door. Honestly, whether you’re a wine newbie or a seasoned connoisseur, this place has something special to offer. And if you’re into live music and nightlife, they host concerts too, promoting mental health awareness and a supportive vibe. Want to bring the kids? No problem, their interactive seating chart helps pick out the best spot for everyone, from front row Mike Dawes shows to budget-friendly options like Buzz Poets. Keep an eye on their schedule because, trust me, you won’t want to miss the next big event!

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 that hosts a diverse lineup of live performances and events throughout the year. Fans can enjoy stand-up comedy, musical concerts, and cultural shows in an intimate setting that captures the city's lively spirit. In june 2026, the winery will feature renowned comedian Kevin Nealon performing on June 19th at 8:00 pm and again on June 20th with three shows at 7:00 pm and 9:30 pm. Music enthusiasts can look forward to performances by artists like Billy Allen & The Pollies on June 7th at 8:00 pm, and the talented Vincen Garcia on June 6th at 8:00 pm. The summer months also bring a variety of musical acts, including The Clunkers on June 12th, Brownie Mary's Kelsey & Co. on June 26th, and the folk band The Deslondes on july 7th at 8:00 pm. Other notable performances include Larry McCray on July 17th, East Nash Grass on July 11th, and Sierra Sellers on July 3rd. The venue continues its entertainment lineup into the fall with shows like Mike Dawes on october 21st at 8:00 pm, Chet Vincent on september 5th, and Aaron Rowe on September 18th. Additional events feature cultural performances such as Flamenco Pittsburgh: Duende - A Student's Journey on may 31st at 5:30 pm, and comedy nights like Standup In The Cellar on May 30th at 8:00 pm. With such a dynamic schedule, The Original Pittsburgh Winery promises unforgettable experiences for all attendees, blending entertainment, community, and the city's rich cultural tapestry.