City Winery Brings Live Music, Comedy, and Wine to the Strip

Published by Jeremy. Last Updated on June 8, 2023.

Disclaimer: Our site uses demographic data, email opt-ins, display advertising, and affiliate links. Please check out our Terms and Conditions. Pricing, operating hours, or menus may have changed since our initial visit and may not be reflected in subsequent updates. Please confirm these directly with any business or attraction prior to visiting.

City Winery has been taking the entertainment world by storm with its unique combination of being one part winery, one part entertainment complex.

While City Winery has been operating in several major cities in the USA for many years now, their first Pittsburgh location opened right in the heart of the Strip District in the Terminal building complex in 2023.

Wine, live entertainment, and late-night hours in the Strip? We're in for that!

Winery Meets Entertainment at City Winery

City Winery Pittsburgh

Time and time again one of the biggest complaints we hear about the Strip District is that things close early. For the longest time if you made it down past about 3 pm things felt like a ghost town beyond a few key restaurants and a couple of clubs.

Thankfuly, this is changing, and the Strip Distric it's becoming a late night hub with new bars, breweries, and event spaces moving in with each passing year.

City Winery has a unique concept that blurs the bar and entertainment complex line. In the front of the house is a conventional bar where you can order housemade wines, cocktails, and food. Behind the bar is a sprawling, two-floor space full of tables, yet another bar, a decently sized stage, and a rather epic view from the balcony on the upper level.

City winery Wines

So whether you are visiting to simply try one of their wines, ranging from immensely drinkable sparkling Cava to Riesling, Cabernet Sauvignon, and more grown the world over, or to take in a show, you can really have a solid night out here no matter your interest.

In fact, the show element of City Winery almost overshadows their wines completely due to the robust lineup that is scheduled in any given week. Shortly after opening ticketed shows included the likes of a Johnny Cash tribute ban, a Taylor Swift Dance Party (coinciding with a concert week), jazz, live poetry, and even standup comedy to name a few.

Pinot Noir from City Winery

Throw on that shows are generally scheduled four to five nights a week and City Winery is aiming to become a premier entertainment hub in a neighborhood that sorely needs it. 

Buy Tickets in Advance for a Show

Live Music at City Winery

As City Winery's venue can only be described as an intimate space, we'd be remiss if we did point out that this means tickets are inherently limited. Even at opening, many events were selling out well in advance.

Most shows sell tickets with assigned seats for Stage Premier (closest to the stage), Premier (behind that), High Tops (in the back), or Balcony seating (in the upper level). Tables and hightops generally seat four to a table, and as of this review most shows did not require purchasing all four seats. As such, it is entirely likely you could be splitting a table with a new friend during your visit. (The only seats that are not grouped like this appear to be the balcony as they face forward and run the width of the venue.)

Bar at City Winery

Some shows do appear to sell tickets as general admission seating as well; however, due to the variation you will do well to book your tickets as early as possible in case assigned seating is offered for the show. That said, as the venue seats only about 250 for any given show (our estimate), you'll be hard pressed to have a bad view anywhere in the venue.

For those who plan to be regulars to concerts at City Winery, you may want to look into their Vinofile membership as well. This paid subscription allows early access to ticket sales, no fees, and earning points for purchases redeemable for future tickets. The Plus version of the membership also includes a bottle of wine and a complementary wine flight every month and other perks, and could offer an enticing option for regulars of the venue!

Overall, we're really excited that City Winery finally opened a Pittsburgh location and we're really excited to usher in the return of night time activities in the Strip District with many visits to this one in the future!

City Winery Pittsburgh is located at 1627 Smallman Street in the Strip District. We visited this one for a media preview night at opening. As always, all opinions are our own.

Leave a Comment