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.
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.