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Over the River and Through the Shipyard to O'Leary's Seafood

Jan 09, 2014 12:55PM ● By Cate Reynolds
By Gail Greco // Photography by Tony Lewis, Jr.

Along the shores of the smaller Chesapeake Bay creeks and rivers, marinas bustle with boats en route—you always wonder where and why—and others in for a fix. Commercial ports of safe harbor, shipyards are also for docking recreational boats, drawing us to browse the waterfront out of curiosity and even romance. Boatyards are the grit of a seafaring area, and their environs serve up not only the local sailing culture but often the culinary one, as well.

On a recent visit back to historic Eastport, I hungered for what the waters serve up on a plate, as well as the plank. So I motored over the Spa Creek Bridge by Annapolis Harbor to Third Street, passing up other eateries to get to O’Leary’s, almost at the end of the little street that meets the harbor. The first seafood place on what is now considered Eastport’s restaurant row, O’Leary’s is as I remembered it: nestled around cajoling leafy maples and the familiar clapboard exterior now dressed in a fresh coat of sea-aqua paint.

Inside were the cozy and rich sienna wood-stained posts and beams, which were added in 1983 when Tom O’Leary bought the 100-year-old crab shack and turned it into a 75-seat fine-dining restaurant—keeping the old boat-hauling winch building the restaurant now uses as a storage shed. The view through mullioned floor-to-ceiling windows once fully exposed the waterfront, but a new piece of shipyard real estate was erected in 2005. So that is now the focal point, as well as the spire of St. Mary’s church, and the tops of countless sailboat masts rising above it all.

Image titleIn 1998, artist and entrepreneur Paul Meyer bought O’Leary’s, continuing the lively waterside eatery tradition that locals depend on and newcomers savor. That evening, I was neither local nor newcomer, just a fan meeting a friend. So while I waited, I took in the amber autumn sun setting over the harbor, faintly stenciling the spire and the masts against the sky. I simply basked in the wait…long, deep breath out with a smile at the end of it. Precious moments like these—away from the routine and responsibility—set up an evening for dining and relaxation.

Chris, one member of O’Leary’s en pointe staff, was attentive with the wine list, where a white was calling to me for a change, perhaps because a creamy chardonnay by Hahn was available by the glass. In fact, there are some 27 wines a la stem—originating everywhere from California and Washington to Spain, France, New Zealand, Italy, Australia, and South Africa. O’Leary’s also offers a formidable 100-label wine list—from everyday bottles to special-occasion varietals to vintages oenophiles would choose and some wines that are still improving with age.

Once my friend sat down, I offered her the choice of starters, which included shrimp, crabmeat, scallops, and lobster. But she pulled me right up from the bottom of the boat with her challenge of oysters, a seafood I usually pass up. I suggested that we go for the ones baked with bits of prosciutto, garlic, and Parmesan, rather than the batter-fried or fresh-shucked in cocktail sauce. Actually, I should have asked for a mix of all three, as the latter came with a mustard lime remoulade. But the Italian-style oysters were so luscious, I helped myself to seconds from her plate. It just goes to show you how eating at such a trusted restaurant can snap you out of culinary profiling to try something new.

O’Leary’s sources ingredients as local as possible, such as the oysters, as well as the grouper, crabs, and rockfish pulled from the bay or, when in short supply, the Carolinas. The restaurant also mixes in authentic flavors from markets afar. We choose salads, sharing both a fresh beet with smooth Humboldt Fog goat cheese and a perky autumn pear with a tumble of delicate greens and Michigan cherries.

Entrees are mostly seafood, except for a Filet Mignon Marsala, Pork Tenderloin Gorgonzola, andImage title Maple Leaf Breast of Duck. The Grouper with Gulf Shrimp sounded enticing, accompanied by a tomato cilantro salsa and chipotle aioli. So did a rockfish Provencale-style. My friend settled on a soft-shelled crab plated along with a crabcake broiled with a special house sauce. Beyond the bay, seafood offerings come from far-reaching waters, including a fresh-water barramundi from Australia, yellowfin tuna from the Pacific, and mahi mahi from Florida.

I went for the whole Maine lobster special, sassily dressed in a skirt of fluffed risotto and a hem of scalloped tail flippers, a most couture peplum shape any mermaid would want to don on a date with a squid. The crustacean’s nose was up in the air, but I think not so much because of the pride and pomp it was plated with, but as a nod to the décor on the wall, with its claws pointing toward owner/artist Paul Meyer’s own fancy canvases of modernist impressionism that make up the restaurant’s wall décor.

Taking the evening slowly, we found room for dessert, choosing the key lime mousse over the chocolate, and it arrived as a pouf of creamy tropical tang coddled in a nutty almond tuile. A raspberry truffle cake was of high contrast—white and dark chocolate layered with whole fresh seasonal raspberries in a glistening fruity coulis. I was longing for a coffee, and the restaurant offers several Viennese roasts with liqueurs and flavorings. I tried the O’Leary’s Godiva with chocolate, hazelnut, and spicy rum. It warmed the heart again for a good ole standby restaurant I am sure will still be here the next time I get over the bridge to meet up with a longtime friend, and talk until the lights go out over the creek and the shipyard sleeps.

Gail Greco is a food and home interiors writer and photo art director/stylist. Author of 16 cookbooks and TV producer/host for the Discovery Channel and PBS, she is a culinary Knowledge Partner at Yahoo and chef/editor of the DuPont Tefl on cooking website. She lives and works on the Eastern Shore and in Sarasota, Florida.

O’Leary’s Seafood Restaurant
310 Third Street, Annapolis
Appetizers: $12-$15
Entrees: $29-$35