Not only is Middleton Tavern one of the oldest restaurants in Annapolis, with patrons like George Washington, Thomas Jefferson and Benjamin Franklin, but Middleton's also has an amazing music schedule!  Every Friday and Saturday, they have a great piano bar.  Wednesday night is "Annapolis Unplugged" .   And as you can see below, they have entertainment all the time.  

For more information on Middleton Tavern, be sure to check their website.