If you're looking for an upscale bar with live music, the Oak Room is a perfect pick. The crowd is a mix of the mature and middle aged; people coming for food/appetizers, late night drinks, and after special events. They have a live piano player and some patrons are very enthralled in the music (including the guy next to me who pretended his table was a keyboard...) The Oak Room is the perfect location for a nice evening of live music and fine cocktails.
I went to the Oak Room recently to celebrate a friend's 30th birthday and it was fairly busy for a Saturday night. There was a wait for tables after 9:00 p.m. The cocktails are priced around $20, which are of the highest in Boston. I would say wearing something around business casual is fine, while there were some in full suits and dresses. It is one of the more mature drinking establishments in the city. Boston is known for being fairly casual, but this is one of the more elgant bars.
Pros: Interesting drinks, live music
Cons: Expensive drinks
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