Historic Eastport in Annapolis, MD

Eastport is a neighborhood of Annapolis, Maryland. Annexed to the city in 1951, it has its own particularly unique history.

The area played an important role during the American Revolutionary War as an encampment area for Lafayette’s troops on their way to Yorktown, and as the site of Fort Horn which protected the city harbor from the British fleet. It played the same protective role during the War of 1812. Consisting mostly of farmland through the mid-nineteenth century, the area began to be developed after the establishment of the United States Naval Academy in Annapolis. Many workers at the USNA, as well as those who worked in the maritime trades made their homes there. Today, Eastport, located just across the bridge from the City Dock area of Downtown Annapolis, is the maritime district of America’s Sailing Capital.

The residents of Eastport respect their uniqueness so strongly that in 1998, when they felt their neighborhood would be hurt by the temporary closing of the Eastport bridge for repairs, there was a tongue-in-cheek “secession” from the city. The “Maritime Republic of Eastport” was established. “War,” in the form of an annual “Tug of War” that raises money for charity, was declared. Relations between Annapolis and the “Republic” remain friendly, though, and, in 2009, Josh Cohen, a former resident of Eastport and one of the “Founding Fathers of the Republic” was elected mayor of the city of Annapolis.

Just across the bridge from Eastport, in Annapolis MD, there are museums to visit and historic homes to tour. You can tour the Naval Academy. Members of the Annapolis Yacht Club, one of the oldest in the country, participate in Wednesday night sailing races. These races can be viewed from the bridge and waterfront eateries on both sides of the bridge. The Annapolis Boat Shows are held annually in October. Annapolis Restaurant Week, when three-course offerings can be had for a set price, gives diners the opportunity to try various restaurants. Among the many things to do in Annapolis, a trip — even a walk across the bridge — to historic Eastport is a must!

Eastport, Annapolis accommodations run the gamut from historic inns to whole house rentals. There are several B&Bs in Eastport, one of which is the Eastport House located in a building dating from the 1860s. It is located at the corner of First Street and Severn Avenue. Contact Annapolis Accommodations if you are looking for longer term rentals, week-long stays for the USNA Commissioning Week or the weeks during the Annapolis Boat Shows in October.

Like other Annapolis restaurants, Eastport restaurants offer a wide variety of cuisine and ambiance choices.

O’Leary’s Seafood restaurant is the perfect place for a casually elegant meal. O’Leary’s menu concentrates on seafood prepared creatively.

Carrol’s Creek is another seafood restaurant which offers fine dining on the waterfront. Open for lunch and dinner, Carrol’s Creek has an extensive wine list and offers live music in its lounge on Saturdays. You can eat outside on the deck and watch the Wednesday night sailing races in the summer, or grab a hot drink and watch the Parade of Lights in early December.

Seafood restaurants are not the only choices by far. Serious steak lovers can be more than satisfied in Eastport.

Lewnes Steak House is owned by a family with a long restaurant history in Annapolis. Their wine selections match their prime steaks perfectly. The portions are huge, and there are small touches that recall the family’s Greek origins. Ruth’s Chris is also located in Annapolis. This renowned elegant restaurant is walking distance from Lewnes. For either, however, we recommend reservations.

Chart House Annapolis is accessible by water taxi, and provides views of the U.S. Naval Academy. As it is part of the Chart House chain, diners can be assured of excellent steaks and seafood and specialty desserts. There is a Happy Hour, featuring small plates, from Sunday through Thursdays afternoons. Brunch is also served on Sundays.

For more casual dining, there are two Eastport favorites. Davis’ Pub serves 7 oz. Angus burgers, quarter pound hot dogs, soups, and sandwiches. All of the “Pub Favorites,” however, feature crab, and their crab pretzel is legendary. Davis’ also provides an outdoor seating area. Another well-known Eastport establishment is the Boatyard Bar & Grill. Known by some as the best sailing bar in Annapolis, it is also family friendly. It serves breakfast, lunch and dinner daily. Along with a raw bar, the Boatyard serves casual foods, including sandwiches, soups and pizzas. There are specials for each weekday.

If you want to try your hand at kayaking the Annapolis Harbor, you can rent kayaks — or buy them — at Spring River located just off the water at 311 Third Street.

The USNA and the sails of a boat from the Chart House in Eastport, Annapolis

Quaint and rich in history, it is no wonder that Eastport was named an “Outstanding Neighborhood in the State of Maryland.”