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.