If "Mad Men" protagonist Don Draper came to Annapolis, he would dine at OB's Prime. The restaurant, situated above O'Brien's on Main Street, is accessible through a discreet side entrance that is almost reminiscent of a speakeasy.
Once inside, the setting is luxurious and intimate, with a stone fireplace, leather chairs, a wine bar and cigar bar for after dinner relaxation. The Board Room, as it is called, is available for private functions for up to 15 people.
The cocktail and wine list is extensive, and the steaks are the prime course. Also offered are succulent appetizers, classic salads and decadent desserts. While OB's Prime is not the only steakhouse in Annapolis, it enjoys the distinction of not being part of a chain.