O’Brien’s Oyster Bar and Restaurant in Annapolis, Maryland is a historical and distinguished dining venue that offers the best food, the best entertainment, and the best prices. While placing emphasis on Chesapeake Cuisine, guests don’t leave disappointed thanks to our unique approach to Annapolis Hospitality. Visitors will marvel over the classic and traditional styling of O’Brien’s as the walls bear artifacts of sports heroes, the Naval Academy, and Annapolis history while embarking upon some of Annapolis’ most delicious food and beverages. Listen to entertainment nightly, or dance your heart away on the weekends on Annapolis’ most popular dance floor.