Eastport: The Other Side of Annapolis

If you want to experience the real Annapolis, the maritime Annapolis, the place that gives this town the working man’s right to lay claim to the title “Sailing Capital of the Nation,” you’ve got to venture out of the historic district, mosey across the bridge at the foot of Compromise and Duke of Gloucester Street, and head into Eastport.

You’re on the earthier side of town, the place where you’ll find the majority of marinas, yacht designers, boat builders, boat brokers, sail makers, surveyors, chandleries, crabbers, and the local watering holes of the maritime crowd where you can tune into a little bit of the current nautical gossip.

Here you’ll find the maritime history, some of it housed in the exhibits of the Annapolis Maritime Museum. The museum, located on Bay Shore Drive at the foot of Second Street and Back Creek (phone: 410-295-0104) is open Thursday-Sunday from 12 p.m. to 4 p.m.

Eastport is an eclectic mix. Million-dollar homes bump up against marinas, modest homes sit next to expensive renovations, and boat yard workers rub elbows with high tech types that have recently moved into offices with waterfront views. In spite of the diversity, everybody seems to work together. The business association and civic and religious groups join hands on projects like Christmas in April, Holiday Sharing, GreenScape (an annual cleanup and spring planting event,) and fundraising for local causes and improvement projects.

Many Eastporters worked at the Naval Academy, the marinas, the yacht yards, and the seafood plants. Eastport houses such famous yacht yards as the Annapolis Yacht Yard, which built torpedo boats during World War II, the Trumpy Yacht Yard, (now the Chart House Restaurant) and the Mason Yacht Yard. You’ll see all of these spots on the Eastport Walking Tour, which starts once you cross over the bridge from downtown Annapolis.

Much of Eastport’s history comes out of the Yacht Yard period. While it has colonial roots – other than sporting a Fort on Horn Point, built as part of the defense of Annapolis in the summer of 1776 – it remained farmland until the l800’s. To get to Annapolis by land took several hours on horseback. It was the establishment of the United States Naval Academy in 1848 that prompted the first change.

Anxious to develop the area to house workers, the Mutual Building Association built the first bridge over Spa Creek. It was a wooden one, and ended at present day 4th Street. Its current configuration dates back to the 1950’s. So does its association with Annapolis, which formally annexed Eastport in l951.

When the Eastport Bridge was shut down for repairs in 1998, Eastporters staged a mock rebellion and officially declared themselves the Maritime Republic of Eastport. It was a public relations gimmick to call attention to businesses in Eastport while the bridge work was going on, but the mock rebellion stuck. It still goes on in the form of rebellion reenactments, rope tugs of war between the Historic side and the Eastport side of Spa Creek, numerous special events, and now the “Search for Ben,” a Colonial Governor whose grave seems to be missing. Speculation has it that he is buried on the site of the Annapolis Yacht Club Annex, which at the time of his burial was the family farm.

By Arlene Kay Berlin