O'Brien's Oyster Bar & Grill

Annapolis Maryland has an abundance of historical locations. From the oldest Statehouse in the union to the landing place of Kunte Kinte. Annapolis has history covered, so of course the town’s favorite bar and grill is is deeply embedded in the history of the city as well as the United States itself. In fact, you might argue that the history piled in every brick of the building is what makes O’Brien’s so good.

113 Main Street is a part of history. The building has seen over 200 years of Annapolis’ evolution. Built in 1774, as the Rose & Crown, this tavern was once a local gathering spot for both Royalists and Revolutionaries. In fact, the popular pub was an attractive spot for political intrigue as it was a major gathering space in a major port. By 1836, 113 Main Street had tuned into Sam’s Café, the only dining and dancing establishment in downtown Annapolis. This was Annapolis’ Golden age and 113 Main Street had already established itself as a waterside tavern that served as a portside communications network, long before there was an internet. Sam’s Café became the meeting place for merchants, sailors and locals alike. Discussing trade, politics and enjoying entertainment, 113 Main Street was the social centerpiece in downtown Annapolis.