Eastport's Historical Significance
Absent of the cobblestone streets and stately 18th-century mansions seen in its neighboring district of Historic Downtown Annapolis, just across the Spa Creek Bridge, you’ll find the charming seaside community of Eastport with a rich history all its own.
Established in 1655 and officially founded in 1868, Eastport was the backbone of a rapidly growing maritime economy in early America. An independent town until annexed to Annapolis in 1951, this spot served as the docking point for 19th and early 20th-century bugeyes and skipjacks, delivering thousands of oysters, and was also a hub for exporting tobacco and importing guns, sugar, and rum.
Following the Revolutionary War, indentured servants and newly freed slaves settled, started businesses, and owned homes. During that period, Eastport was primarily occupied by watermen, glassmakers, oyster shuckers, meatpackers, and domestic workers - a true working-class community. After the establishment of the Naval Academy in 1845, the area generated even more employment opportunities and spurred the development of additional housing for its workforce.
In 1998, more history was made. That year, the Maryland State Highway Administration placed a temporary shutdown repair of the Spa Creek Bridge connecting Eastport and Downtown Annapolis, which caused an uproar amongst locals. Residents were angered by the length of the interim closure and feared Eastport businesses would suffer from losing this vital route. In response, a group of locals met in a pub and the idea for the Maritime Republic of Eastport was born. Their mission was to devise a creative way to promote and encourage the patronage of the neighborhood’s enterprises, and declaring independence as a mock secession did just the trick.
Though its independence as a self-proclaimed micronation isn’t recognized by any world government, it’s highly favored by residents and the peninsula adopted its very own flag to show its pride as one. Even the City of Annapolis respects this jocular claim and has a bit of fun with it, too - every year both Eastport and Historic Downtown participate against each other in tug-of-war across Spa Creek.
The neighborhood has seen an influx of professionals from its earliest working-class days, yet it maintains its nautical heritage as a bustling port. The combination of its maritime history, relaxed Chesapeake lifestyle, and delight in community backs Eastport’s motto: “We like it this way." And, there’s no doubt you’ll like it, too.
