Issue: October 2008
Eastport Exposed

With its own maritime industry, dining scene, history, coat of arms, charity events and rabble rousers, Eastport is one quirky neighborhood, says Jeremy McGeary. But thanks to its sense of camaradarie and good fun, the whole of Annapolis is the better for it.

by Jeremy McGeary
photographs by Vince Lupo

The familiar skyline of spires, domes and water tanks appeared across the horizon as we rounded Tolly Point. And as if on cue, we encountered the same weather phenomenon I remember from years back--the one that seems to greet me whenever I sail to within sight of America's Sailing Capital. From lazing along, sheets eased, we were all of a sudden strapped in hard and bounding into that gusty northwesterly that whistles out of a clear sky and whips down the Severn River. We flew along in the sparkling, exhilarating combination of flat water and stiff breeze that brings sailors in droves to Annapolis. Only this time, we weren't going to Annapolis--that is, not the Annapolis beneath the golden dome of the tourism brochures.

Our destination was Eastport. Yes, strictly speaking, Easport has been part of the city of Annapolis since it was annexed in 1951, but in culture and spirit it's a place apart, a place that bears its own rich maritime history, which it leavens with a generous measure of light-hearted anarchy. In other words, it is a place separated from its older, dressier sister not only by the narrow body of water that is Spa Creek, but by a sense of ubiquitous camaraderie and fine sense of humor.

This wasn't my first visit to Eastport, but my trips had always been part of a larger visit to Annapolis in a general destination sense. This time I wanted to see Eastport under its own colors, so I steeredAlmost Crazy, the Sabre 34 my wife Melissa and I had chartered from Hartge Chesapeake Charters, toward Back Creek, which, along with Spa Creek and the Severn River, forms this narrow peninsula's water boundaries. As we drew close, Eastport raised its leafy canopy, obscuring the capitol dome, the last visual reminder of Annapolis proper, and drew our attention to its own more modest landmarks.

Just inside Back Creek, and flanked by a few modern office buildings and marinas bristling with Eastport's ever-present sailboat masts, is the McNasby Oyster Company building. McNasby was the last to close of more than a dozen oyster-packing houses that once crowded the Eastport waterfront. Now the building, spared from the bulldozer but nearly destroyed by Hurricane Isabel in 2003, lives on as the Annapolis Maritime Museum, created to preserve the memory of a once thriving industry and to portray the lives of those it supported. The fate of McNasby Oyster Company and the others has been the fate of traditional watermen in Annapolis as well. First elbowed out of Annapolis across the creek, they were then eased out of Eastport, as late 20th century attitudes changed about what constituted the "best use" of water-front real estate. Helping to close the door behind them was the decline of the oyster and crab fisheries throughout the Chesapeake Bay.

For 200 years, from the time it was first settled to the mid-19th century, the Eastport peninsula remained largely farmland, while across Spa Creek, Annapolis accumulated the trappings and population attendant to its status as state capital of Maryland. In the 1860s, houses began to rise on plots laid out around a gridwork of streets, which also provided access to the creeks for watermen. In 1870, the first bridge was built to connect the growing community with Annapolis. The name Eastport, along with its first post office, appeared in 1888. The annexation of Eastport in 1951 enabled the city to maintain a commercial connection to the Bay while keeping the working-class Eastport citizens, begrimed with the mud of the Chesapeake and the sawdust of shipbuilding, at arm's length.

We tied up at Eastport Yacht Center, not far from McNasby's. From our berth there, a scan of the shoreline through the intervening screen of masts revealed modernist office buildings abutting boatyards abutting modest duplexes of indeterminate architectural provenance abutting once identical cottages now expanded into mini McMansions.

A short stroll brought us to narrow streets lined with tiny front yards, where flowers and ornamental shrubs in profusion hug porches and doorways of residences and businesses alike. Many of the houses have been refurbished. Some are architecturally faithful, others tricked out with glitzy additions, and no small number--tended but not splendid--suggest that residents share pride in their community equally across the spectra of income, origin and expression.

And amid all this contrast, a constant: boats--boats in driveways, boats in yards, boats from creek to shining creek. It seems that even among evidence that the neighborhood has shifted toward a residential neighborhood, boats are its glue. Some people live here to work on boats, others so they can sleep with boats all around them.

Also on display on many of the homes and businesses were flags. We saw a good many Stars and Stripes, but most abundant was a yellow flag bearing a coat of arms complete with dogs, boats, a heron and a crab. These were flags of the "Maritime Republic of Eastport." Several of these were prominent around the Maritime Museum, which we'd walked by on the way out of the marina and dropped in to make further inquiries.

Jeff Holland, the museum's director, was a founding member of the Republic, and its Minister of Propaganda. He talks fondly, but modestly, of the heady days when the smell of revolution lent its smoky tang to the air of Eastport. (Here the commodity burned was socks, not the tires favored by the inveterate protesters of Europe.) The community between the creeks thrived in the 1980s and 1990s by providing the support services for the yachts that sustained the aura of the Sailing Capital. This economic dependency hung on a slender connection: the Spa Creek Bridge. But in the winter of 1998, the bridge joining Eastport and Annapolis was to be closed for repairs, and would remain so for several months. This bode ill for Eastport, because alternative routes would divert much essential traffic far from its businesses, recalls Holland.

On Super Bowl Sunday, while the rest of America was encouched before its televisions, a group of Eastporters (aka Eastportoricans) took to the streets, set up a barricade at the bridge, and declared that, far from being hurt by the closure of the bridge, Eastport had no further use for Annapolis. Eastport thereby seceded from Annapolis, and would be known henceforth as the Maritime Republic of Eastport (MRE).

Although tongue in cheek and, as all the instigators will admit, inspired by beer in belly, the idea for a Maritime Republic of Eastport resonated with its residents, who joyfully took up the call. The jubilant revolution gained nationwide media attention, ultimately attracting droves of visitors to share in its spirit--and bring their trade to its businesses.

When the bridge eventually re-opened, the Republic and Annapolis restored diplomatic and commercial ties. But the good-humored rivalry has persisted and is acted out in the annual Tug-of-War across Spa Creek (a body of water known in the Republic as the Gulf of Eastport). Genius or serendipity, whatever governed the outcome, it was providential; the madcap caper not only saved Eastport from a local recession but gave birth to a 501/C3 civic organization that has since raised thousands of dollars for charities and created a new and lighthearted sense of community. "Ten years later," says Holland, who is today referred to by younger revolutionaries as a Greybeard, "the level of volunteerism is just spectacular, and the Tug-of-War and the .05K run across the bridge, which began as stunts, are now huge fundraisers for other nonprofits, like the SPCA and the Maritime Museum."

As Melissa and I wandered the streets we sensed this communal rapport, and quickly understood the significance of the "retrievers rampant" on the coat of arms. In MRE heraldry, dogs and slobbered tennis balls convey welcome to visitors in Eastport.

Old Eastport is defined by a grid of three avenues and six streets that extend from Spa Creek to Back Creek, with the Severn River at its tip. First Street is the easternmost. Sixth Street marks its western limits and leads to the bridge to . . . well, you know where.

Running east-west, Severn Avenue parallels Spa Creek and Chester parallels Back Creek. Maritime businesses of all stripes line the water sides of these avenues. Between them, flanking the central Chesapeake Avenue, the area is largely residential, except along Fourth Street. As the approach to the original Eastport bridge, this was the community's early commercial center and remains so, but businesses like the Baltimore Cupcake Company indicate the degree to which the neighborhood has evolved from its recently downscale flavor.

Cupcakes weren't going to provide the sustenance we needed after our rugged nine-mile sail from Galesville. We found that instead in the Boatyard Market across the street, where a laundromat used to be. In an atmosphere of varnished wood paneling and marine art, we dove into deli sandwiches and salads while a friend and former colleague regaled us with tales of the changes he has seen in Eastport in the 17 years he's had an office there.

The Boatyard Market is a recent expansion of the Boatyard Bar & Grill, on the corner of Fourth and Severn, a site formerly occupied by a series of unsalubrious watering holes. In 2001, Dick Franyo opened the family- and sailor-friendly Boatyard in an essentially all-new building (a vestige of the old remains to perpetuate the zoning). He sees its location as the anchor at one end of what he hopes will become a revitalized Fourth Street commercial area.

Franyo has kept a boat in Eastport since the 1980s, a house since the 1990s, and when he retired from a banking career decided to make the community his avocation as well as his home. He uses the Boatyard Grill to promote the welfare of both Eastport and the Chesapeake Bay, from which it earns its keep and its character.

Suitably fortified, Melissa and I set out to beat Eastport's western bounds. These lie in the vicinity of the Eastport Shopping Center, which we, sandal shod, felt was about the limit of a casual stroll on a warm June day. So we strolled back to the boat, admiring the neighborhood's quiet charm.

We had dinner at Davis' Pub, which offers wholesome bar fare in surroundings where we'd have felt equally at home in foulies or uptown finery. A framed poster on the wall explained a sight we'd stumbled across in our earlier meanderings. On Fourth Street we had paused to study what we now learned is the Great Wall of Eastport, a 90-foot mural commissioned by the Maritime Republic and painted by artist Cindy Fletcher-Holden, herself part of the local color. That it's shedding flakes of paint perhaps underlines the fragility also of Eastport's commercial waterfront which, if not stewarded, could yet be eroded.

Day two of our Eastport ramble began with breakfast at the Leeward Market--which may be an unfamiliar name even to some Eastport denizens, because it only recently opened in the premises vacated by Cafe Gurus at Chester Avenue and Second Street. Over coffee and bagels we perused the Walking Tour leaflet we had picked up at the entrance to the Maritime Museum. The tour guides you through a sequence of plaques and displays that describe facets of Eastport's history. You have to walk the walk though--the leaflet only hints at what you might find. Over the course of the next hour or so we encountered several of these plaques while following our own itinerary, which consisted mainly of going up every road until barred from further progress by a home or a body of water. (Most of the avenues and streets end at the water, and provide public access to it, some of them through miniature parks.)

At one such termination we found ourselves at the Severn Sailing Association, where children of various ages and skill levels were preparing for sailing lessons that would soon fill the Severn River with a cloud of small sails. Here we were able to add to our store of seafaring wisdom: "Tiller toward trouble! Tiller toward trouble! Don't hit the . . . Oh!" pleaded the college-age instructor to her class of beginner sprites who were getting the feel of Optimist dinghies by bouncing them off each other and the three bulwarks that formed a sort of protective corral. Her advice sounded like a reasonable way to steer around many of life's hazards.

From there, we cut through the Yacht Haven complex, where the whine of air tools and the smell of fresh varnish spoke of an industry moving at a fever pitch. Now we were in the thick of Maritime Eastport, where within the circle of a swung cat (I refer, of course to a cat-o'-nine-tails, not a feline companion animal) we could, had we a mind to, have browsed for a boat, bought it, insured it, berthed it, had it restored and maintained, and sold it.

At the core of all this activity is 222 Severn Avenue, where, in the last century, a sequence of shipyards had turned out fishing boats, torpedo boats, and pleasure boats according to the market of the moment. When the last of them, John Trumpy & Sons, closed its doors in 1974, the big wooden sheds on the to-die-for site, with its peerless view of downtown Annapolis, seemed destined to be replaced with high-rise condominiums. But traditionalists envisioned with pain an imminent eclipse of the historical foundation on which Annapolis was built and staged a revolution of their own. So in response to the two high-rise condominium buildings already on the shores of Spa Creek, the city's leaders placed a moratorium on condominium developments. In 1987, city records show, this emergency measure was codified into zoning ordinances that preserve areas occupied by maritime businesses.

We walked under the looming, brick bulwark of the Tecumseh condominium on Severn Avenue, which serves as a reminder of what might have happened if the city had taken a different tack.

With residential development off the table, the Trumpy yard could have been a cold property but for the vision of Jay Templeton, owner of the nautical instrument company Weems & Plath. He acquired it and converted its structures into a warren of offices and workshops to house a multitude of marine-oriented trades and businesses. The symbiosis generated in this veritable yacht-services mall has won awards for the develop-ment and made it a model to be imitated by other communities with a similar maritime heritage to preserve.

One of its first tenants was the Chart House restaurant, which has for 30 years now occupied the former service shed built over the water. It's an Eastport landmark, not just for its impressive physical presence on Spa Creek, but for the experience of dining under its windowed walls and lofty roof. Looking out its wall of windows is like dinner theater, with Annapolis Harbor for its stage, the boats that ply it in ceaseless evolutions its players.

Our next stop was to be Annapolis Canoe & Kayak to rent a couple of kayaks. As we made our way there, another of the great historic boatsheds echoed with a rousing chorus of "Aaaarrrrgggghhhh!" in treble voices, as a single file line of children in pirate attire emerged at a stealthy crouching gait. They were about to embark on their Pirate Adventures of the Chesapeake voyage through Spa Creek. An afternoon of discovering sunken treasure and defeating the evil Pirate Pete might well leave these youngsters with a lifelong taste for pursuing activities on the water.

At Annapolis Canoe, Melissa and I climbed into our kayaks to trace Spa Creek to where it emerges from the marshes of nether Eastport. Above the bridge, we met a host of Optimist prams under rainbow-colored sails, rollicking in the gusty westerly breeze: another batch of youngsters embarked on an apprenticeship to sailing. On our left, we passed two of the neighborhood's oldest boatyards, Petrini's and Sarles, which have sustained boatbuilding trades for decades (Sarles has been in operation since 1907). We paddled on, into the marshes, where I peered up at a great blue heron, from which vantage he gained my respect for his stature, not to mention his piratical headgear and armory.

After returning the kayaks, we headed back to the boat to freshen up so we'd present well at the Eastport Yacht Club. A friend had invited us to join him on the club's elevated deck, where we would enjoy sipping cocktails and critiquing the yachts racing on the Severn River. Here in Eastport you can catch a spectacular view of the local racing Tuesdays through Fridays. This was Wednesday, so we got to watch the Annapolis Yacht Club's diverse classes skirt past the club. A thunder shower and subsequent rainbow enlivened the start, and another squall ensured a few dramatic moments, spectacularly backlit by the lowering sun, as the boats tacked toward the finish line between the moored craft in Spa Creek. Even after walking four blocks to Carrol's Creek Cafe at Annapolis City Marina, we could still watch from our table as the stragglers inched their way to the finish line to join the melee of boats jammed between it and the bridge. We learned later that we could have seen video of the evening's events over nightcaps at the Boatyard, where sailboat racing replaces the usual cable fodder on the restaurant's TV screens. Yes, in Annapolis, they sail 'em hard and put 'em away wet--most of them in Eastport.

On departing Eastport the next day, I couldn't resist the urge to cruise up Back Creek to gaze on the boats that inhabit every inch of it: power, sail; classic, modern; elegant, clunky; J World and Mears Marina on the Eastport side; Port Annapolis and titanic Bert Jabin's marina across the creek. Boats inhabit nearly every inch of Back Creek, all the way to its marshy end. It's always an inspiration to me to study the variety of permutations of function and style in which the boating fraternity expresses its passions. If boat design is still to a degree experimental, Eastport is the laboratory storeroom.

It was time to bring Almost Crazy home, so we eased out of Back Creek, taking care to honor the dogleg in the channel. As we sailed toward Tolly Point, we looked behind us and watched as Eastport diminished in the view and Annapolis once again rose into prominence. If that's the way the world is ordered, so be it. Eastport may not have the visibility or the recognition that Annapolis does, but after our little sojourn wandering its characteristic streets, we agreed that the motto on the MRE flag, "We Like It This Way," needs no explanation.

Jeremy McGeary "grew up" in England and left when he discovered he could make a living sailing, then building boats, then designing them. He now spends much of his time writing about boats and sailing when he'd much rather be on the water. He was an associate editor atCruising Worldfor eight years before moving to Virginia's Northern Neck.


Getting into Eastport is easy—just follow the well marked channels into either Back Creek or Spa Creek, but don't try to cut the corner between the two. Leaving should be as straightforward, but be warned: Eastport is one of those places a cruising sailor pulls into one October because there's a boat show going on, then wakes up one morning five years later and wonders where the time went. Transients without number have been absorbed into Easport's population of kindred spirits and workforce.

Anchoring is permitted in Back Creek, and there's a public dinghy dock at the foot of Sixth Street. You may also anchor in Spa Creek off the Naval Academy and above the bridge.

Moorings are available on a first-come-first-served basis. There are only five in Back Creek but many more in Annapolis Harbor and above the bridge in Spa Creek. Call the harbormaster (410-263-7973; VHF channel 09, 17) for an assignment.

Marinas: Unless otherwise noted, these marinas have transient slips, electric, laundry and showers. On Back Creek:  [1] Horn Point Harbor Marina (410-263-0550;; no laundry. [2] Eastport Yacht Center (410-280-9988;; repair services. [3] Mears Marina (410-268-8282;; pool, tennis courts. On Spa Creek: [4] W&P Nautical (410-268-7700;; next to the Charthouse; no laundry. [5] Annapolis City Marina (410-268-0660;; fuel, restaurant. [6] Sarles (410-263-3661;; no laundry. [7] Petrini's (410-263-4278); no laundry.

Point of Interest: [8] Annapolis Maritime Museum (410-295-0104;

Restaurants: [9] Leeward Market (410-295-0601); break-fast and lunch only. [10] Harbour Deli (410-263-5276); breakfast and lunch only. [11] Boatyard Bar & Grill (410-216-6206;; [12] Davis' Pub (410-268-7432;; [13] Chart House, (410-268-7166;; [14] O'Learys Seafood (410-263-0884;;  [15] The Rockfish (410-267-1800;; [16] Carrol's Creek Cafe (410-263-8102;; [17] Lewnes Steakhouse (410-263-1617;; [18] Ruth's Chris (410-990-0033;

The [19] Royal Farm carries basic groceries, but for provisioning you'll need to take a cab to the supermarkets on Forest Drive. At the [20] Eastport Shopping Center, you'll find the Eastport Deli (410-263-8313), a drugstore, liquor store, Aah, Coffee! Cafe (410-990-9111;, Squisito Pizza (410-990-9800), Adam's Ribs (410-267-0064; and a few other carryouts.