You may not recognize it during the boat shows, but this is Annapolis at its busy best--and it's your oyster. We're here to show you how to crack open the shell...
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The hardest part about dining in and around Annapolis is not getting there, or getting reservations, or beating the crowd, or finding a cuisine that suits you. No, the hardest part by far is simply deciding where to eat. Crabcakes and seafood, steakhouses, pan-Asian, Italian, tapas, pizza, Mediterranean, Thai, sushi, French, Mexican, gourmet cheese, gourmet potatoes? You name it, the 'Nap has got it—and much of it is within easy walking distance of the boat show.
Of course we can't possibly give you detailed reviews of each restaurant and eatery, but we can break it down for you geographically, divvy it up into three basic dining districts: (1) City Dock, (2) Main Street, (3) what we're calling Upper Downtown, comprising Church Circle, State Circle, Maryland Avenue the first block of West Street, and (4) Eastport.
Of course if you're at the boat show, you are at City Dock—however unrecognizable it may be compared to what it looks like the rest of the year. And that just makes it all the more convenient for dining purposes, because City Dock, and hence the show, is virtually surrounded by eateries. Hard against the southwest bulkhead of Ego Alley, the narrow fairway that reaches in to City Dock from Spa Creek, is Pusser's Caribbean Grille—part of the Annapolis Marriott Waterfront and so close to that edge of the show that it might as well be part of it. On the opposite side of the show and Ego Alley, lining Dock Street are the Phillips Crab Deck, Armadillo's Bar & Grill and Dock Street Bar & Grill (purveyor of surprisingly fabulous crab cakes) as well a Starbucks, Pip's Dock Street Dogs, Storm Bros. Ice Cream, and a Moe's Southwest Grill. Just off Dock Street you'll find Sofi's Crepes (Craig Street) and, on the other end of the block on Randall Street, Big Cheese (sandwiches and gourmet cheeses) and the Corner Cafe.
And of course at the north corner of the show you'll find the distinctive red-brick building that is Middleton Tavern—with its small pub entrance on the Randall Street side and its broad awning-shaded porch, usually full of diners, crowding Pinkney Street and looking across to the northeast end of Market House. The latter, Market House, was finally reopened this summer after sitting idle for several years. Inside, elbow to elbow and lining both sides of one big high-ceiling space, are half a dozen eateries—ranging from an oyster bar to a popcorn booth to an express version of Chick & Ruth's, the iconic comfort food hash house just two blocks away on Main Street.
The culinary parade on the landward side of Market House—a short street called Market Space, where you'll find the very popular McGarvey's Saloon (next to Middleton), Maria's Sicilian Ristorante, Federal House Bar & Grille, and two coffee houses (City Dock and Hard Bean) and, right at the bottom of Main Street, Buddy's Crabs & Ribs—another high-volume comfort food place, this one with the added advantage of a great second-story view of the waterfront.
Now it's time to take on Main Street itself—and brace yourself; it's a big job. Down near the bottom of Main, tucked in between the Museum Store and Mills Fine Wine & Spirits, is Mangia Italian Grill. Heading up the hill from there, you'll come first to O'Brien's Oyster Bar & Restaurant, with the new OB's Prime steakhouse stashed all but invisibly next door, then the Acme Bar & Grill, followed by the aforementioned and curiously popular Chick & Ruth's Delly—where everyone stands for the Pledge of Allegiance at 8:30 every morning.
And that's just the first block. At Conduit Street, the southside gauntlet continues—with the very highly regarded Osteria 177 (Italian-Mediterranean), Cafe Normandie (French, of course, and very cozy), then Nano (Sushi), the Red Red Wine Bar, Castlebay Irish Pub and Joss Cafe & Sushi Bar. Across from these latter two, sweet-tooths should know, are the Annapolis Ice Cream Company and, in a small shopping gallery at 188 Main, Nostalgia Cupcakes. Farther up on the north side is Piccola Roma, a white-table cloth Italian bistro, and then, finally, near the top of the hill, the famous and formidable Treaty of Paris Restaurant. Oh, and another Starbucks.
See? You thought we were exaggerating, didn't you? But, if you've been keeping count, that's 39 places to eat, and you can still see the boat show tents from here.
See that grassy, tree-lined circle ahead, with the big church in it? Quite logically, that's called Church Circle, and it marks your arrival at what can be best described as upper downtown. There's only one eatery of note on the circle itself. That is the venerable Reynolds Tavern and—through the 2012 Boat Show at least Sly Fox Pub. (We’re told the Sly Fox will close in mid-November, and the owners will subsequently open a new pub, The Foxes, on Main Street.) You can have lunch or afternoon tea on the first floor of the beautiful old main building, built as a tavern in 1747, and food or drinks in the Sly Fox, occupies a multi-level courtyard along the Franklin Street.
Heading east by way of School Street, you come to the historic district’s other, larger circle. That would be State Circle, picturesque home of the Maryland State House, and of Harry Browne's Restaurant—a favorite, for obvious proximity reasons, of politicos and state employees. Here too there's a cozy bar (upstairs) and just a bit of scenic outdoor seating on the brick sidewalk. A few doors away, at Cornhill Street, there's Potato Valley Cafe, devoted to exactly what the name suggests: potatoes, baked and jazzed up to order. And just down nearby Maryland Avenue, chock-a-block with shops, you'll find yet another Irish pub—Galway Bay.
Now it's time to head to upper downtown's own restaurant row—the first block of West Street. Here, like Main Street, most of the action is on the south side of the street. Working your way down this side, you'll come first to the almost-famous Rams Head Tavern—or, to be exact, first you come to Rams Head On Stage, Annapolis's cafe-style, big-namish concert venue, and then the Rams Head Tavern, birthplace of Fordham Brewing Company . . . and many a good hamburger. Then, just beyond a small and very yellow coffee shop, Cafe Olé, you'll come to the popular local hangout Stan & Joe's Saloon, the local-music oriented 49 West Coffehouse, then Tsunami (pan-Amerasian, for lack of a better word) and finally the justifiably popular new small-plate restaurant Level. Working your way back up the north side of this block of West Street, you'll find the lovely Luna Blu Ristorante Italiano and the popular Mexican restaurant El Toro Bravo.
If you go south from City Dock, along Compromise Street and past the Marriott, you'll soon come to the drawbridge that takes you across Spa Creek and into the Eastport neighborhood. Here, among the many maritime businesses that the area is zoned to favor, you'll find another heaping handful of restaurants that are worth the half- to one-mile walk.
Not far from the southern foot of the bridge, at the corner of what is now Sixth Street and Severn Avenue (one of only three streets that run the length of the Eastport peninsula), you'll first come to The Rockfish, a mild-mannered seafood restaurant that becomes a bona fide loud-band bar on weekend nights. Turn left on Severn Avenue and, just after Fifth Street on the left, you'll come to a gated parking lot that serves, among many other maritime businesses, including Annapolis City Marina, Carrol's Creek Restaurant—where, with any luck, you can get a seat on the deck, overlooking Spa Creek.
At the Fourth Street end of that block, on the opposite side of Severn Avenue, is the always-bustling Boatyard Bar and Grill—so popular with local boaters that some say it's the new Marmaduke's—the famous nearby watering hole where many a sailing story and lie was told, until the place went under in the late 1990s. Just across 4th Street is Lewnes' Steakhouse, a comfortable family-owned business that's been on this corner, under one name or another, since 1921. At the other end of that block, at Third Street, is a Ruth's Chris Steakhouse. (This is what in fact replaced Marmaduke's—physically, if not spiritually.)
Across Severn Avenue on Third Street is O'Leary's Seafood Restaurant—which, for those who may remember the original O'Leary's, is very different (and, many say, much better) since 1998, when it came under new ownership. Go one more block down Severn and hang a left at Second Street to find a Chart House restaurant, perched at the edge of Spa Creek. A chain, yes, but notable for its splendid view of the creek and for its location—in a massive boathouse where Trumpy yachts were once built, and before that PT boats, and before that more luxury yachts (Chance Brothers).
You've covered most of Eastport by cruising Severn Avenue, but there are a few more spots to mention. Near the Back Creek side of the peninsula, on Second Street, is Leeward Market, a combination cafe and grocery. Two blocks up Chester Avenue from there you'll find the famous, and famously funky Davis' Pub. And, if you've got the legs for it, check out the tasty Vin 909 Winebar, new occupant of the intimate bungalow that used to be the Wild Orchid Cafe (now on the West Street circle).
Yes, it's a lot to consider, a lot to choose, a lot to choose from. But really now, when it comes to keeping your taste buds happy, is there even such a thing as "too many choices?" No, of course not. Bon appetit!