Pittsburgh's premier venue, restaurant, winery, and event space. Live music, comedy, and wine events in an intimate venue with good food, a full bar, and great wine. Part of The Strip District Terminal, City Winery Pittsburgh is a welcoming space to indulge your senses with music, wine, and food.
Many customers praised the attentive and friendly service, highlighting specific staff members who went above and beyond.
Atmosphere
The venue is frequently described as having a fun, cozy, and intimate atmosphere, ideal for live performances.
Food Quality
While some enjoyed the food, many reviews noted that it was overpriced and inconsistent in quality, with some dishes receiving mixed feedback.
Seating Comfort
Several customers expressed discomfort due to tight seating arrangements, making it difficult to enjoy the performances.
Entertainment Value
The live shows and performances received high praise, with many customers expressing their enjoyment and eagerness to return.
CJ
Carly Jerome
1 day ago
2.0
We had such a mixed experience here today. We came for the Beyonce drag show. First, the good!
The drag queens were great and the vibe was awesome. They get five stars.
The bad? Woof. Our server was probably the worst server I’ve ever had. She spent most of the time hanging out at the bar and ignoring her tables. The poor people next to us were there for OVER AN HOUR before she came to take their food order. We saw her once after the show started and even then we had to ask someone to grab her for us. We couldn’t even get refills, which is wild at a drag show. She was incredibly rude and short with all of the groups around us. At the end when we were paying our checks, a different server came and helped cash out our tables because we were all waiting so long. In fact, I think the group next to us dined and dashed because it was unclear that she was coming (vs the bill being tied to our tickets). That’s how long it took. It was the WORST service. Absolutely horrendous. I saw other servers hustling, so it sucks we got someone who very much couldn’t hide the fact that they didn’t want to be there.
We ordered a meat and cheese tray. It was mediocre; not really enough food for the value nor good enough quality for the cost. I ordered a mocktail - apparently they got rid of all their mocktails and to no one’s surprise our server didn’t have any recommendations for alcohol free drinks except coffee. So I ordered a cold brew and cream and the cream never came. Cold brew was fine but the value was lacking as well.
Wanted to love it, especially since the queens were so spectacular! It was horrendous and I can’t imagine we’ll ever come back, even for the queens. There are plenty of other drag show options in the region.
MZ
Matt zebroski
1 day ago
5.0
Just played there with the Alex skolnick trio. We had a wonderful time. Dani was amazing with hospitality. The sound was perfect. Sound tech Mike was super professional and quick. The food was great. The Pinot noir was actually great and I have really hated city winery wine in the past lol. I'm happy about that. The wait staff was super friendly. The room sounded good. We had a good crowd. They promoted well. They communicate well before the show. The load in is easy with a big ramp in the back. Parking is easy. Great show. Thanks guys.
MB
Michael Benjamin
3 days ago
3.0
City Winery as a winery and events venue are amazing. My wife and I have tried salsa dancing, brunched with drag queens, and laughed out loud with George Lopez. And the wine. Well, you really can’t miss that up. But as a restaurant, it’s laughable. Not only is the food way overpriced, you get appetizer-sized plates. Ok ok, sure, American portions are usually huge, and you know, maybe it’s great. But the food is average. I’m paying overpriced, undersized money for average food? And now it’s mandatory???? City Winery, how about you improve the quality of your food? Maybe that’s why you enacted that rule?
Only recommend for the events and wine. The food? It changes every now and then, but all 3 times, it’s been absolutely disappointing.
ES
Eileen Schmitt-Metz
5 days ago
5.0
We celebrated our 21st Anniversary tonight & Jahlani made it extra special. He was extremely kind, professional and attentive during our dining experience. Thanx Jahlani for making our anniversary an enjoyable evening!
Eileen & Gordy Metz
CG
CC G
Nov 7, 2025
3.0
The place almost is a great place. I appreciated the opportunity to see a comedian I like in a small venue, but the food and drink are really not even close to worth the prices, even given what we were there for. It was fine/okay, but way overpriced. And the tables were so small, we really couldn't comfortably fit things. I expect some of this, but it was just too much.
Frequently Asked Questions About City Winery Pittsburgh
What types of events can I attend at City Winery Pittsburgh?
City Winery Pittsburgh hosts live music, comedy, and wine events in an intimate venue.
What are the opening hours of City Winery Pittsburgh?
City Winery Pittsburgh is open Monday to Friday from 4 PM to 10 PM, and on Saturday and Sunday from 12 PM to 9 PM.
Where is City Winery Pittsburgh located?
City Winery Pittsburgh is located at 1627 Smallman St, Pittsburgh, PA 15222, US.
How can I contact City Winery Pittsburgh for reservations or inquiries?
You can contact City Winery Pittsburgh by phone at +1 412-246-1000.
Does City Winery Pittsburgh have a menu available online?
Yes, you can view City Winery Pittsburgh's menu online at http://www.citywinery.com/pittsburgh/menu.
Where can I find updates or videos about events at City Winery Pittsburgh?
City Winery Pittsburgh shares updates and videos on their TikTok page at https://www.tiktok.com/@cwconcerts.
What kind of dining and beverage options does City Winery Pittsburgh offer?
City Winery Pittsburgh offers good food, a full bar, and great wine in a welcoming atmosphere.
Which fitness centers are near City Winery Pittsburgh for visitors looking to work out?
Nearby fitness options include Solidcore, a pilates studio and gym, and Mayweather Boxing and Fitness Strip District for boxing classes and workouts.
Are there any entertainment venues near City Winery Pittsburgh to visit before or after an event?
Yes, guests can visit Terror Town, a nearby theatre for arts and entertainment, or Room16, a local dance club.
What nearby dining options complement a visit to City Winery Pittsburgh?
Nearby restaurants include Balvanera, an Argentine restaurant, Chipotle Mexican Grill for casual dining, and Aruba Island Bowls Cafe for health-focused meals and smoothies.