Eastport is a distinctive neighborhood in Annapolis, Maryland, with a rich and unique history. Annexed to the city in 1951, Eastport played a significant role during the American Revolutionary War as an encampment site for Lafayette’s troops en route to Yorktown and as the location of Fort Horn, which protected Annapolis harbor from British forces. The fort continued its defensive role during the War of 1812. Originally composed of farmland through the mid-19th century, Eastport saw significant development following the establishment of the U.S. Naval Academy. The neighborhood became home to many USNA workers and maritime tradesmen.

Today, Eastport is known as the maritime district of Annapolis, America’s Sailing Capital, located just across the bridge from the City Dock area. In 1998, residents humorously declared "secession" from Annapolis when the temporary closure of the Eastport Bridge for repairs threatened to isolate the community. This led to the creation of the "Maritime Republic of Eastport" and the annual "Tug of War" event, which raises money for charity. Despite this lighthearted rebellion, relations between Eastport and Annapolis remain friendly, and in 2009, Josh Cohen, one of Eastport's "Founding Fathers," was elected mayor of Annapolis.

A walk across the bridge to Eastport offers easy access to Annapolis’ museums, historic homes, and the U.S. Naval Academy. Visitors can watch the Wednesday night sailing races hosted by the Annapolis Yacht Club, one of the oldest in the country, from waterfront restaurants on both sides of the bridge. Eastport is also home to the Annapolis Boat Shows each October, and Annapolis Restaurant Week provides a perfect opportunity to sample local cuisine. With its vibrant maritime history and close-knit community, a visit to Eastport is a must for anyone exploring Annapolis.