Skip to main content

Eastport: the other side of Annapolis

I began hanging out in Annapolis when I left the Baltimore Evening Sun in 1962 for a feature-writing position at the Washington Evening Star, a job that lasted nearly 20 years.

I began hanging out in Annapolis when I left the Baltimore Evening Sun in 1962 for a feature-writing position at the Washington Evening Star, a job that lasted nearly 20 years.

Neither newspaper survived but I did, eventually morphing into a boating writer thanks partly to discovering sailing after relocating in the early 1960s from Baltimore to Anne Arundel County, Md. Even though editors pointed out that my focus on sailing wasn’t the way to succeed as a Washington newspaperman, I stubbornly persisted and began writing a weekly sailing column.

Annapolis, then undiscovered by tourists, was mostly about locals, watermen, boatyard workers, sailors and politicians (when the state legislature was in session). “Remote” Eastport was a gritty, working-class neighborhood across the Spa Creek Drawbridge from the more genteel Historic Annapolis. Eastport has since caught up with the times, especially in real estate values. But even tourists haven’t changed its laid-back character, and I am still at it with a resident sailboat — and a desk, chair, laptop and cell phone squeezed into a corner of a small, maritime rental compound. These days I sail more than work and also travel, a side benefit to being semiretired but still active in the writing game.

Annapolis, of course, has long attracted sailors with its deep-water creeks, natural harbor, Colonial history, the NavalAcademy, ship chandleries, boatyards and boatbuilders. I came to meet many colorful boating types who relaxed in Eastport’s hard-scrabble saloons after a hard day’s work in the maritime industry.

Sailing took a firm hold in my life in 1970, when I purchased in Washington an older 32-foot varnished mahogany sloop. I moved it to Spa Creek, which is still home to my latest boat, the classic fiberglass Sailmaster 22 I have owned for 23 years. The boat is only five minutes from my telephone booth office, and it calls me often like a siren.

Eastport continues to meet my recreational, professional and social needs — such as they are — although in real life I sleep in Severna Park, home for 43 years. Eastport has many advantages. Unlike downtown Annapolis, for example, parking spaces are still relatively available here, with no meter maids pouncing to write tickets — a constant threat across the harbor.

A few of my boating friends can often be found during happy hour at a new sailor’s hangout, the Boatyard Bar & Grill, a pleasant cottage similar to a Cape Cod bar. Places like this provide an excellent opportunity to meet boat-friendly types, and you might also be able to hitch a ride in a Wednesday Night Sailboat Race.

Dick Franyo’s Boatyard preceded other bars on the same site, such as The Wharf and Patton’s Pub. And it became the natural successor to the beloved Marmaduke’s Pub, Eastport’s original sailor’s bar a block away on Severn Avenue. Duke’s closed in 1998 and became an expensive chain steak house, sending shocked regulars scurrying to other public houses.

Duke’s was where I first met one of Eastport’s most colorful resident characters, “Budweiser Dave” Sells — a wiry, piratical-looking, hard-working Travelift operator at a real Eastport boatyard. He shows up at the other Boatyard on weekends, downing numerous Bud longnecks (hence the nickname) and serenading young women in a deep, wavering baritone. His photographic portrait hangs on a kind of wall of fame along with images of other Eastport types, including Melbourne Smith, a builder of historic replica vessels, and marine surveyor Fred Hecklinger, whose knowledge of yachting history is uncanny.

The Boatyard opened in 2004 and is informally upscale but not outrageously so. It expanded last spring when it displaced the community’s only coin laundry, popular with cruising sailors. The Boatyard Market next door to the mother lode has a wine shop, deli, high-powered espresso bar and its own pastry chef.

This is one of five bar-restaurants along Severn Avenue, the east side corridor of the harbor, but it’s where locals speak the peculiar boating language. It’s also where devotees of elite yacht racing watched the America’s Cup match racing live from Spain over breakfast (with a $1.95 surcharge for toast) and mourned the disgraceful downfall of the only U.S. syndicate.

Excellent waterfront views of the busy Annapolis Harbor are offered on the west side of Severn Avenue at Carrol’s Creek Café, which has a large outside deck, and the enclosed Chart House, at eye level with the water in a work shed that was part of the famed Trumpy Yacht Yard compound. Another establishment offering a sliver of water view (through a forest of masts) and off the beaten path is Davis’s Pub, a locals hangout where regulars sit glued to the same bar stools afternoon after afternoon by the front door. Here questions can be answered regarding drywall, plumbing, house painting, roofing, electrical issues and construction in general.

Once a bar catering to neighborhood blacks, the small brown building on a corner lot at the foot of Fourth Street on the Back Creek side of Eastport offers sidewalk dining, and dogs (leashed) are welcome. Out front is a small public dinghy dock with a 4-foot depth at the end. Davis’s is one of the rare Annapolis restaurants serving real Maryland crab cakes made with real Chesapeake Bay crabmeat in season — picked and canned in Hoopersville on Maryland’s lower Eastern Shore. (You can’t get more local than that.) This is a pet peeve of mine because most local restaurants serve imported, tasteless crabmeat and pass it off as the U.S. species of “blue crab,” which it is not. A 4-ounce crab cake at Davis’s (please, Saltine crackers, not a burger bun) is $10.

By far the most delightful water view is from the deck of the Eastport Yacht Club at the foot of Severn Avenue, but it’s only for members and their guests. A visit to Annapolis would be totally incomplete without experiencing the best view of Chesapeake Bay aboard a Woodwind schooner operating out of the Waterfront Marriott Hotel on City Dock. Two sister ships, measuring 62 feet on deck and flying four sails, offer walk-on daysails five times a day. This isn’t a motorized excursion but a two-hour, two-

masted experience under full sail with dozens of guests paying $31 during the week and $34 on weekends.

Woodwind, swift and stiff with a modern underbody, usually sails five miles across the Bay to the Eastern Shore’s Kent Island or the Bay Bridges. It is a family-owned operation, with Ken Kaye and Jennifer Brest, father and daughter licensed Coast Guard captains. For information, call (410) 263-7837 or visit .