Annapolis Neighborhood Guide

Annapolis is dominated by history and water. Tourists come to see the wooden dome of the State House, visit the U.S. Naval Academy, wander down cobbled streets past 18th- and 19th-century houses or take a pleasure cruise on one of the many boats moored at the city's docks and yacht clubs.

Amid the guided tours and Colonial landmarks, though, Annapolis has even more to offer: seriously great seafood, a night-life scene that ranges from wine bars to local sailors' pubs, alfresco art events and stylish boutiques.

It's funny how the city grows with you: As a kid, I ate peanut butter ice cream at Storm Brothers on the City Dock and ran through the gardens of the William Paca House downtown with my brother. Decades later, I come back for leisurely afternoons on the water and to visit dives that serve crab balls alongside cans of Natty Boh.

Here's a guide to our longtime favorites and recent discoveries.

More: Photo Gallery: Discover Annapolis | Visitors: How to soak up the water

 
 
1

Galway Bay Irish Restaurant

63 Maryland Ave., Annapolis, MD 21401-1629  | 410-263-8333
Annapolis has a range of Irish and Irish-inspired pubs, from chains (Fado) to brewpubs with rollicking live music (Castlebay). The best of the lot is Galway Bay, situated among antique shops and specialty stores on Maryland Avenue. There,s no TV or loud music to drown out the buzz of good conversation, and you can actually chat with bartenders as they pour perfect pints of Guinness. You never know who you'll run into in the dark, cozy bar -- midshipmen, college students, neighbors, Gov. Martin O'Malley ...

Be warned, though: The bar area is narrow, and the small booths fill quickly. There have been times when friends and I popped in for oysters fried in Guinness or excellent corned beef and cabbage to find there was only enough counter space to rest glasses of beer and whiskey. Not that we complained. More...
2

Level

69 West St., Annapolis, MD 21401  | 410-268-0003  |  Web site »

You don't get much in the way of trends when it comes to Annapolis night life: DJ lounges, bars with dozens of microbrews on tap, bottle service -- all foreign concepts on the shores of the Severn. It used to be that way for cocktails, too, until John Hogan and John Miller opened Level in late 2009. With years of mixology experience between them and resumes that stretch from Las Vegas to Washington, the pair craft drinks as good as anything you'll find in Washington's high-end spots, and for far less cash. (Everything on the menu costs $8 or $9.) Take the Tru Outlaw: organic, small-batch Tru gin, organic Citry orange liqueur, house lavender bitters and the house lemon sour mix. It's engagingly floral and slightly sweet. On the other side of the flavor spectrum is the Smoked Margarita, made from Herradura tequila smoked with hickory and lavender and served with lime, sweet agave nectar and smoked sea salt -- it's as flavorful as it sounds. And for traditionalists, it's hard to beat the house's 1944 Mai Tai, based on Trader Vic's original recipe.

All the small plates coming from the kitchen are made with locally sourced ingredients: grilled Japanese eggplant topped with feta cheese, smoked salt and olive oil; crispy veal sweetbreads; gnocci drizzled with truffle oil and spicy pepper flakes. Whether you go for dinner or cocktails, stick around for weekend DJs, when the sleek upstairs lounge -- mirrors on exposed brick walls, no-reservations-needed couches -- becomes a laid-back dance party.

3

Banneker-Douglass Museum

84 Franklin St., Annapolis, MD 21401  | 410-216-6180  |  Web site »

I admit it: I didn't venture to Annapolis to see the Banneker-Douglass Museum. But I was drawn in by the signs that dot downtown's busy streets with the faces of Benjamin Banneker and Frederick Douglass, both among the nation's most revered African Americans and both Maryland sons. I had read "Narrative of the Life of Frederick Douglass" a half-dozen times as a child (it was one of my favorite books), so once I realized it was there, I had to see what the museum had in store.

Inside the red brick and stained-glass facade of the Banneker-Douglass Museum -- built around the circa-1876 Mount Moriah A.M.E. Church, the first African American church in Anne Arundel County -- one will find far more than the stories of the men on the signs. It's a treasure-trove of local history that you won't find anywhere else; before my visit, I didn't know a thing about Maryland's elite African American beach community, Carr's Beach. In spite of the segregation that necessitated it, it was one of the coolest places to be in the '50s and '60s. Nor did I know of local explorer Matthew Henson, who was among the first people in the world to reach the North Pole. The museum is small, ultra community-focused and tends toward the hodgepodge (one exhibition was simply of old photographs of various get-togethers snapped by a well-known local shutterbug), but for history buffs and locals, it's a must-see.

4

Red Red Wine

189 Main St. , Annapolis, MD 21401  | 410-990-1144  |  Web site »

Red Red Wine is the kind of wine bar that complains loudly in its mission statement about how it dislikes wine snobs and wants to "demystify" "juice" for the "disenfranchised" who are turned off by the jargon and technicalities of the wine world. (Is it any surprise that the description of one wine on the menu claims "The guy from 'Sideways'" would hate it?) The constant "Us against the world" mentality gets to be a little much, but there's a lot to like about this funky new spot, opened at the end of July by Fox news anchor Brian Bolter and his wife. There are 40 wines by the glass and a decent selection of themed flights, all of which have such names as "Baby Got Blanc" or "Girl Junot It's True." (The Three Little Chards, which pulls chardonnays from France, California and Chile, is educational.) Four wines are available on tap -- the Gotham Project Riesling from New York's Finger Lakes is a warm-weather thirst quencher -- and the menu is full of interesting nuggets about the winemakers and grapes. The food is mostly paninis, personal flatbread pizzas and salads; there is also an interesting cheese menu.

Mismatched decor, huge banquettes, elaborate chandeliers and a wall of old wooden doors behind the bar make for an eclectic place to hang out and sample a few glasses. Friday and Sunday evenings feature live funk and blues or occasional sets from Washington's engagingly experimental violinist Matthew Hemerlein.

5

Horse Boutique

158 Main St. , Annapolis, MD 21401  | 410-626-9726  |  Web site »

It must be the proximity to water that makes Annapolitans so darn preppy. Pop into a few of its boutiques and you'll understand: The Pink Crab is awash in Lilly Pulitzer dresses that seemingly come only in nautical blues and whites, blushing pinks and grassy greens. The brightly printed dresses at Diva seem made for yachts and afternoon croquet matches.

Horse Boutique, on the other hand, comes off like the neighborhood bad girl with its sea of navy, gray and black designer duds, better suited for a night in the city than a night on the water. Announced by a bold neon-orange sign on a hectic stretch of Main Street, the boutique carries a highly curated list of small labels -- and a few big ones, including Cynthia Vincent and Tibi -- that even D.C. shoppers might find only online. Horse is where you go to lust after a demure Porcelain silk blouse printed incongruously with guns, and a chunky cocoon sweater from Jamison, and to snap up a pair of daringly tiny punch-colored shorts or neon-bright accessories to pair with -- gasp! -- a gray dress. (With prices often in the $200-$300 range, it's in no way cheap chic, but the sale section is full of deals.) It's fair to say that Horse is fashionistas' best-kept secret in Annapolis.

6

Maryland Hall for the Creative Arts

801 Chase St., Annapolis, MD 21401  | 410-263-5544,301-261-1553  |  Web site »

It's a little bit of a shocker when you realize that Annapolis's growing arts scene -- which includes galleries as well as the Annapolis Opera, Annapolis Symphony Orchestra and the Ballet Theatre of Maryland -- lives in a freestanding building that looks, smells and feels eerily like your old high school. In fact, it is a schoolhouse of sorts, with classes ranging from "Art and Yoga" for children to ballet for teens to charcoal figure drawing for adults. But although you instinctively expect a bell to ring, it's music that rings out from this arts hub. There are concerts on the lawn (the next one, with the Robert Redd Quartet, is Wednesday); and a plein-air painting festival and exhibition dubbed Paint Annapolis (Sept. 29-Oct. 30). The Ballet Theatre will present "Aladdin," which was selected by an audience vote, Oct. 21-23 on the main stage. And in the basement, City Dock's popular Hard Bean Cafe maintains an outpost that churns out cappuccinos with a trendy La Marzocco espressso machine. Stop by during a visit to the galleries, and find yourself a world away from the docks.

7

The Rockfish

400 Sixth St., Annapolis, MD 21403  | 410-267-1800  |  Web site »

You don't have to look far to find good seafood in Annapolis, and such spots as O'Leary's, Hell Point and Chart House are well-known destinations for crabs, oysters and rockfish.

In Eastport, just across the bridge from downtown, the Rockfish Raw Bar & Grill holds up the city's reputation as a seafood destination in a dining room that is younger and more lively than some of its brethren. While the menu includes plenty of turf to keep the ocean-averse happy (look to the burger and short ribs), the smart money is on creamy, cheesy crab dip, plates of raw oysters, sauteed littleneck clams, fish tacos heavy with battered cod and spicy slaw, and lightly bound, low-filler crab cakes.

The huge restaurant has plenty of booths and tables, but the friendly bar staff and excellent draft and cocktail options make dining at the bar an enticing option.

8

Boatyard Bar and Grill

400 Fourth St., Annapolis, MD 21403  | 410-216-6206

Eastport is the sailing capital of Annapolis, home to marinas, sailmakers, sailing supply stores and yacht brokers.

In the middle of it all is Boatyard Bar and Grill, a comfortably loud bar, restaurant and raw bar where every inch of wall space is covered with a museum's worth of boat models, nautical photos, yacht club burgees and old signs advertising boat-builders. Current weather conditions for the Chesapeake Bay play on a TV monitor. It's not unusual to spot some ruddy-face person wearing a red Mount Gay baseball cap, an indication that they've competed in the prestigious race around Barbados. No wonder this is where everyone heads to celebrate and commiserate after the Wednesday night boat races at the Eastport Yacht Club.

There's way more to Boatyard than a place to suck down a pint glass (yes, really) of rum and tonic. The kitchen sends out the kind of crab dip you rave about to friends, delectable sandwiches with blue crab covered in spinach and cheese, and a killer plate of beer-battered cod and chips. From the raw bar come creamy oysters from the Choptank River, crawdads, clams and shrimp cooked in beer and sweet onions. On Sundays, brunch features the best Bloody Mary in Annapolis and surprising Eggs Chesapeake -- eggs Benedict starring lump crab meat and Old Bay seasoning. Even if you get seasick on a water taxi, you'll find something to love at this family-friendly spot.

9

Lewnes' Steakhouse

401 Fourth St., Annapolis, MD 21403  | 410-263-1617  |  Web site »

With a warm, friendly staff, wonderfully old-school decor and steaks of obviously superior quality, this family-owned steakhouse bucks the city's reputation as a seafood-only destination. Of course that doesn't mean you shouldn't start your meal with the restaurant's delicious oysters Rockefeller or clams casino. (You have to know your way around bivalves to serve food in this town.) Seafood starters give way to cuts of an incredibly juicy, horseradish-topped prime rib swimming in juices and a three-finger-thick ribeye with a perfectly seared crust.

Wines are available by the glass, half-bottle and bottle, and range from $30 to more than $1,000. The decor brings it all together: high-backed dark-stained wood and leather booths in a warm red dining room are enough to fulfill anyone's "Mad Men" fantasies.

10

Davis' Pub

400 Chester Ave., Annapolis, MD 21403  | 410-268-7432

When visitors leave Davis' Pub, (a) it probably happens grudgingly and (b) if it's not already, they wish it was their neighborhood hangout. Whether it's your first visit or 50th, there's an easy rhythm to this no-frills one-level bar, built in the 1930s when Eastport was a working-class mix of black and white residents.

Settle in on a bar stool, chat with the gregarious bartenders and the regulars sitting next to you, grab a draft beer (Otter Creek, Flying Dog, Heavy Seas) or a can of Natty Boh or Bud, check out the TV schedule to see what's playing on the flat screens -- Orioles and Nationals games play in separate corners of the bar -- and order a basket of crab balls, delightful meatball-size crab cakes that arrive with saltines and creamy dipping sauce. Classic rock, country and '80s tunes play from the jukebox while you make fast friends talking about Maryland sports (note the Terrapins and Johns Hopkins lacrosse gloves hanging from the exposed rafters), your most recent date, current events, boats, whatever -- the bartenders have a gift for getting every person involved in a conversation.

Sure, there's a wharf right across the street, and Davis' helpfully provides sailors with its latitude and longitude on its Web site, but this isn't a stuffy boater's bar by any stretch.

Beyond the craic, the beer and the occasional whiskey shot, this is the best bar food in Annapolis, and that goes beyond the savory jumbo-lump crab cakes and the jumbo pretzel smothered in crab dip. It's typical to find fresh fish and locally grown grilled corn on the blackboard menu behind the bar. Even better, food is served until 1 a.m. And hey, even if you've eaten elsewhere, you'll still find plenty of reasons to stop by.

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