I went to City Winery in Boston once for a concert and it was fine. My issue with the place is that I couldn't really tell who the core audience this place is for. Is it for wine snobs? But then again I see so many concerts and comedy shows held there, so is it also a music venue? Though the artists they tend to book are pretty small and indie for the most part, so even that's a tough draw.

The menu is also really generic - New American stuff that can be found in a myriad of upscale bars and restaurants.

City Winery is just really lacking an identity. It tries to be everything to everyone and the concept ends up feeling flat enough that most would not come back unless their favorite artist or comedian also happened to show up.