The History of O’Brien’s Oyster Bar & Seafood Tavern

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.

Modern Day Bar and Grill

After WWII, 113 Main Street became LaRosa which actually offered the first pizza pie in Annapolis and other desirable amenities, exclusively. By 1964, 113 Main Street became the first Cabaret Theatre in the area. The 70’s brought Fran O’Brien’s, named for the owner who played for the Redskins as a defensive lineman. The steak and seafood menu became a favorite amongst the legislators and politicians of the day, a distinction our little pub still enjoys. 2018 Started with a menu upgrade and focus on American Chesapeake Cuisine featuring local favorites. The décor pays homage to the sports heroes of the Naval Academy as well as the history of Annapolis which is as rich and layered as our delicious food.

Your Favorite Haunted Banquet House

Any property that has been around as long as O’Brien’s has its ghosts and 113 Main Street is supposedly the home to a few. During its long life the building has stood as witness to a variety of notable events, not to mention the use of the upstairs as a place of “ill repute.” The storage rooms, where liquor and other such items are now stored, used to be tiny bedrooms. Luckily, you don’t have to worry about being propositioned by anyone who’s an employee of the building.

Whatever the century or decade, O’Brien’s Oyster Bar & Seafood Tavern at 113 Main Street Annapolis is the place to be in Downtown. With live entertainment nightly and a great menu, the experience can’t be beat.

Be a part of our history by booking your own private event with us! If you would like information about booking our private event space please contact Lisa by calling the restaurant directly or you can email her,

Thank you for visiting!