City Winery is one of those rare places that does many things well. The fully-functioning winery is also an event venue that hosts live music performances as well as food and wine classes; plus, it serves food, too. The menu is Mediterranean-inspired and each dish is listed with wine pairing suggestions. Prefer to pick your own? You've got plenty of choices, with more than 400 labels in the cellar.
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By the Glass or the Case with a Side of Music
City Winery on Varick is the NYC location of a chain that also graces the streets of Chicago.
It's one of my favorite places to enjoy happy hour during the summer months as their sidewalk cafe seating is more of a garden than most. During colder months, it's a great place to enjoy a concert while leisurely enjoying wine and great small plates. Their full menu is wonderful as well.
There are also wine glasses, a club and private dining areas that can be reserved for special events.