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O’Brien’s Steakhouse 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.
No matter what your age, no visit to downtown Annapolis is complete without visiting a true historical landmark with a staff that is dedicated to high-quality customer service and delicious cuisine.
VisitO'Learys Seafood Restaurant is arguably the best fresh-fish seafood restaurant in the region, and without a doubt the best seafood restaurant here in Annapolis. Located off of Spa Creek facing Historic Annapolis and the U.S. Naval Academy, O'Learys serves only the freshest seafood available.
VisitLocated on Market Space in the Historical District of Annapolis, The Federal House is nestled among a shopping and sightseeing haven. Have lunch and experience the unique charm of the world's sailing capital or visit us for dinner to check out Annapolis's extraordinary nightlife. The Federal House, established in 1830, has a handicapped entrance and is pet friendly and partnered with oyster recovery, Navy Athletics, and Paws boutique.
Our menu includes local favorites like our award winning cream of crab soup, tasty sandwiches, fresh seafood, and our newest addition, the Crab Monster. Federal House offers a great dining experience for the whole family. Our friendly and welcoming staff will be happy to help you find your new favorite.
Be sure to check out our events page to see what’s happening at Federal House late night. We have live music during the week, DJ Cuban on Friday, and DJ Dev on Saturday nights respectively, and World Tavern Poker every Tuesday.
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