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The Original Pittsburgh Winery events

There are no events currently scheduled at The Original Pittsburgh Winery. We are frequently updating our calendar, so please check back soon. In the meantime, explore upcoming shows at other top Pittsburgh locations like The New Castle High School, PNC Park, or Grand Casino Arena.
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The Original Pittsburgh Winery tickets & upcoming events

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

Address :
2815 Penn Ave, Pittsburgh, PA
15222, US

Parking:
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

Experience an unforgettable lineup of live performances at The Original Pittsburgh Winery, a premier venue in Pittsburgh, PA. Mark your calendar for exciting events starting in september and continuing into october 2026. On Friday, September 18th at 8:00 pm, enjoy the soulful sounds of Aaron Rowe. The following month, catch Chet Vincent on Saturday, September 5th at 8:00 pm, known for his captivating performances. In October, immerse yourself in the vibrant music scene with Nik Parr and The Selfless Lovers on Tuesday, October 20th at 7:00 pm, and then be mesmerized by the talented Mike Dawes on Wednesday, October 21st at 8:00 pm. Don't miss these incredible shows at The Original Pittsburgh Winery, where live music and great times come together.