Written by Susan Moynihan
One of my earliest food memories is of crabs, from one summer in Solomons Island. My family had rented a house for a week; I must have been 7 or 8. One afternoon, my brothers took me down to the pier and taught me the art of chicken necking. The blues were biting and I happily scooped them up in my net, seeking out the big guys and throwing the smaller ones back into the water to grow for another season. They were ugly in a cute way, with their wiggling whiskers and pinching claws. When we’d filled the basket, my brothers carried it home and I trotted happily behind, thinking up names for all my new pets. When we entered the kitchen, I asked my mom why she had a pot of beer boiling on the stove, and quickly learned the truth. A few tears later, we all gathered around the table and I learned how to crack my first crab. The tasty results put all ideas of crustacean pets out of my mind.
Food works that way. It’s not just about the ingredients, technique, and flavor. It’s about memories and emotions, and in the case of the Bay, the taste of home. My first raw oyster was a Virginia bivalve, eaten with my dad at Westminster Hall in Baltimore after we paid our respects to Edgar Allen Poe. Summers were (and are still) all about sweet corn, the paler the better. Clam strips mean Ocean City and Senior Week. She-crab soup is the perfect remedy after a chilly day on the water.
And crabcakes—done the right way, mind you—mean Annapolis. I’ve traveled the world for years as a writer and have learned the hard way, multiple times, that nothing tastes like a real, no-filler, Maryland-meat crabcake. Even if the chef says it’s the real deal (and they have, too many times to count), it’s usually not; a crabcake away never tastes as good as the ones found in my home state.
The other great thing about food is it gives you reason to explore. Be it driving out of my way to lunch on a favorite waterfront deck, taking a day to sample sips at a local vineyard, or devoting a weekend to slurping up oysters in Virginia’s Northern Neck, food gives me a reason to get out of my house and get out of my routine, whether I’m revisiting an old favorite or checking out something new. And those excursions lead to new memories, which layer onto the flavor of bygone meals. Any time I eat steamed crabs, be it in my own backyard or at a classic, wood-paneled crabhouse somewhere deep in the Eastern Shore, I’m reminded of feasts past, and of that little girl who wanted a crab for a pet—and the meal becomes that much sweeter.
These winners represent the most beloved food memories of our readers and contributors. I hope they inspire you to get out and make some tasty new food memories of your own.
Note: Few industries have been impacted by COVID more than restaurants. Many are using social media to get news out quickly on everything from updated hours to daily specials, so check Facebook and Instagram (or give them a call) before you go.
Best Restaurant
Maryland: The Kitchen at the Imperial, Chestertown
Count on a fresh take on regional ingredients (think bacon-wrapped trout or crab-and-smoked-ham mac and cheese), paired with stellar, unstuffy service at this repeat winner, tucked in a century-old hotel.
Virginia: Dredge, Irvington
Chef/owner Bryan Byrd brings international flavor to the creative menu at this two-year-old eatery, where sake-steamed clams, roasted Cuban pork, Viet-Cajun-style pho and oyster tacos live side by side in tasteful harmony.
Best Seafood Restaurant
Maryland: Steak and Main, North East
Don’t let their name fool you; it’s about more than award-winning beef here. There’s an oyster bar, full sushi menu, crave-worthy entrees like shrimp gnocchi and scallops frites, and a new fish preparation featured each week on the Chef’s menu.
Virginia: Hole in the Wall Waterfront Grill, Gwynns Island
The menu is just what you want on a waterfront deck: fresh fish, straight from the boat and served grilled or fried; low-filler crabcakes with a side of shrimp; oyster po-boys with sriracha mayo; and creative daily specials such as jerk scallops over red-pepper rice.
Best Oyster Bar
Maryland: Sailor Oyster Bar, Annapolis
You’ll always find Maryland and Virginia represented at this outstanding raw bar, alongside East and West Coast contenders, and served with cocktail and hot sauce, plus a vibrant mignonette. Round out your meal with ever-changing slate of whimsical toasts and specials, finished in a toaster oven or with a torch—the extent of their kitchen. Bonus: All shells go to ORP for recycling.
Virginia: Merroir, a Tasting Room, Topping
Rappahannock Oyster Co. sold their bivalves to top chefs around the world before opening this game-changing restaurant in 2011. Their ethos is the same 10 years later: Olde Salts or Rappahannocks raw or roasted, and small plates that let the ingredients speak for themselves.
Best Burger Joint
Maryland: Chad’s, Edgewater
They dropped the word BBQ from their original name because there’s so much more to enjoy, like their smoked burger featuring Creekstone Farms Black Angus beef, roasted garlic mayo and house-made bacon jam. Pair it with smoked wings or ribs drenched in honey-jalapeno sauce for the best of both worlds. And come early; they close at 8 pm.
Virginia: NN Burgers, Tappahannock and Kilmarnock
Get your wood-grilled burger (double patty, Wagyu, or plant-based) topped with Danish bleu, flash-fried onion sticks, sriracha aioli, or a host of other toppings at this cult favorite, with two locations in the Northern Neck. Add in craft beer, fresh-cut ribbon fries drizzled with truffle oil, and save room for a massive shake.
Best Dive Bar
Maryland: Nautical Lounge, Pasadena
Pool tables, a jukebox, neon beer signs as decor, a devoted local clientele, and an attached package store for carry-out—and if you don’t know about it, you wouldn’t even notice it was there. They don’t make ‘em like this anymore, and that’s a shame.
Virginia: Yorktown Pub, Yorktown
This local hangout feels more neighborhood pub than dive bar, especially when you factor in the cozy, wood-paneled walls, brick fireplace, hearty menu, and up-close views of the York River beach. Dive into their extensive beer list, too.
Best Crab House
Maryland: Jimmy Cantler’s Riverside Inn, Annapolis
Yes, this riverfront classic gets a lot of tourists, and often an hour-long wait in high season. But it’s the real deal, family-run for five generations and featuring blues of all sizes, from local waters whenever possible.
Virginia: Crazy Crab, Reedville
Ok, this 20-year-old spot on Cockrell’s Creek doesn’t do steamed crabs. But you’ll find crab dip, crab-stuffed mushrooms, crab cakes (plain or on a bed of fried green tomatoes), and crab-stuffed fish, shrimp or lobster. Sometimes it’s nice to have someone else do the picking.
Best Brunch
Maryland: Killarney House, Davidsonville
A traditional Irish breakfast with rashers, sausage, and black and white pudding is a natural at this roadside tavern. Or maybe the corned beef hash bowl, crabmeat omelet or made-to-order waffles? Bring your appetite and plan to linger: Live music starts at 3 pm.
Virginia: Water Street Grill, Yorktown
Variety is the name of the game, with creole steak n’ eggs, lobster or blue-crab bennies served on a biscuit, and chicken ’n’ waffles with Tennessee hot sauce offered alongside the usual suspects. Their brunch is so popular, they serve it on Saturday and Sunday.
Best Breakfast
Maryland: Driftwood Diner, Shady Side
Enjoy comfort-food breakfast all day, from pancakes and omelets to chipped beef and plump biscuits and gravy. Lunch specials rotate, and some (like Monday’s loaded baked potato soup) usually sell out.
Virginia: Car Wash Café, Kilmarnock
This quirky, downhome spot gets its name from the setting (yep, a former car wash) but its loyal following from the great, homestyle food, served til 11 am, or 2 pm on Sundays. It’s a must when you’re down by the rivah.
Best Maryland Crab Soup
Maryland: Suicide Bridge Restaurant, Hurlock
Take a hearty beef stock base, pack it with fresh veggies, crabmeat and plenty of flavor, and you get a soup worth road-tripping for.
Best Cream of Crab Soup
Maryland: The Wellwood, Charlestown
We’re adding one more accolade to the awards earned by the rich, creamy bisque served at this historic former hunting camp. And extra kudos for just the right amount of sherry.
Best She-crab Soup
Virginia: Irwin’s Pharmacy, Chesapeake
A humble diner attached to a circa-1934 pharmacy isn’t where you would expect to find a stellar she-crab soup, but that’s part of the magic. As is getting yours before it sells out.
Best Seafood Market
Maryland: Kool Ice & Seafood, Cambridge
Owner Dave Nickerson has been buying the best seafood direct from watermen and processing onsite since 1972. Expect great product at reasonable prices, and order ahead if you want your seafood steamed to go.
Virginia: Graham & Rollins, Hampton
This fourth-generation seller ships their Old Point Comfort Brand jumbo lump and crabcakes nationally, but there’s nothing like buying in person. The fresh fish is everchanging, and they’ll fry it up if you’ve worked up an appetite shopping.
Best Oyster Stew
Maryland: Steak & Main, North East
This specialty is made to order all year round, with sauteed shallots, butter, Worcestershire, oyster liquor, cream, and plump, meaty oysters. The 12-ounce crock comes paired with house-made oyster crackers.
Virginia: Harpoon Larry’s, Newport News
Bacon is the secret ingredient to this house favorite, sautéed with corn, green onions, and garlic before the oysters come into the picture. It’s served over mashed red potatoes, and finished with house fish roe.
Best Chef
Maryland: Steve Hardison, Pirate’s Cove, Annapolis
Come for the views, stay for the food at this waterfront eatery helmed by executive chef Steve Hardison. The broiled seafood bake is tops, as are the fish ‘n’ chips and honey-glazed Norwegian salmon. (He also oversees more Irish-tinged menus at sister restaurants Galway Bay, Killarney House, and Brian Boru.)
Virginia: Bryan Byrd, Dredge, Irvington
Chef-owner Bryan Byrd earned his chops in Key West and with his award-winning seafood truck before opening Dredge in 2019. Local sourcing is key to his ethos, be it oysters (raw, fried, in tacos, or on a pizza) from local waters or meat and produce from his sister’s family farm.
Best Local Delicacy
With contenders like this, how could you pick just one? We couldn’t, and neither should you. Everyone is a winner.
Smith Island Cake
The decadent, multilayered cake has been Maryland’s state dessert since 2008, but oral history puts its roots about 200 years earlier. Vanilla cake with chocolate fudge icing is the classic, but we’ll take it in any flavor we can get it.
Berger Cookies
When German immigrant Henry Berger arrived in Baltimore in 1835 and opened a bakery, he had no idea the tasty imprint he’d make with his cake-like cookies, dipped in thick fudge icing. Danke, sir.
Stuffed Ham
The unofficial dish of Southern Maryland takes a lot of work, but the juicy, flavor-packed results are always worth it. Or pick up one to go at W.J. Dent and Sons in Tall Timbers.
Steamed Crabs
Whether you drench yours in Old Bay, J.O., or plain drawn butter, there’s no better way to spend an afternoon than in their tasty company.
Best Dock & Dine
Maryland: Pirate’s Cove, Galesville
There are few better ways to spend a weekend than cruising to this marina, ordering up a seafood platter, and watching the sun go down as live music heats up the deck.
Virginia: Hole in the Wall Waterfront Grill, Gwynns Island
When you’re located on an island, you cater to anyone who can get there. They have nine slips for boats, and the team delivers dockside if you prefer the view from your own cockpit.
Best Local Coffee
Maryland: Rise Up, various locations, Eastern Shore
What began in a humble trailer by returned Peace Corps volunteer Tim Carleton has grown into a national brand, focused on tasty coffee made with sustainable organic and fair-trade practices. Try it at one of 10 locations around the Bay.
Virginia: Mobjack Bay Coffee Roasters, Yorktown
Avid coffee lovers Celeste and Jo Gucanac have been sourcing and roasting specialty beans for the perfect cup since 2007. The Yorktown Colonial blend features varietals used in the Revolutionary era, roasted in their circa-1720 headquarters in historic Yorktown Village.
Best Bar
Maryland: Galway Bay, Annapolis
A slew of local and imported beers on tap, an award-winning whiskey collection, tasty food, and live music most evenings make this bar a winner, as does its friendly tribe of locals. Don’t come for the game because they don’t have TVs, preferring the art of conversation over competition.
Virginia: Surf Rider Restaurants, various locations
Founded by mom and son Liz Massey and Stanley Bennet in Virginia Beach in 1980, it’s still family owned, with seven locations sharing the same casual beach vibe, great food, and generous staff that is equally welcoming whether you pop in for an hour or stay from afternoon through evening.
Best Distillery
Maryland: Lyon Rum (Windon Distilling), St. Michaels
Founder Jamie Windon traveled and tasted rums around the world before founding her distillery in 2013. The focus is handcrafted, double-distilled rums in myriad varieties, some ideal for sipping and some made for mixing.
Virginia: Copper Fox Distillery, Sperryville
Innovative distiller Rick Wasmund has been called a mad scientist for his innovative approach, incorporating apple, cherry, and peach woods in a one-of-a-kind distilling process that’s led to numerous awards and international accolades.
Best Cidery
Virginia: Sly Clyde Cidery, Hampton
This coastal cidery, named after co-founders Tim and Doug Smith’s cheeky grandfather, sells canned and keg cider made from Virginia-grown apples. Visit their HQ in Phoebus for draft-only creations, plus food trucks and live music.
Best Winery
Maryland: Chateau Bu-De Winery & Vineyard, Chesapeake City
Brenda and Warren Dedrick’s winery spans 440 acres originally owned by 17th-century cartographer Augustine Herrman, with dual labels Chateau Bu-De and Bohemia Manor Farm. Enjoy a well- balanced Blanc
de Blanc sparkling at their airy tasting room overlooking the Bohemia River.
Virginia: Saude Creek Vineyards, Lanexa
Part of the Colonial Wine Trail, this 100-acre vineyard is located midway between Richmond and Williamsburg, on the site of a Revolutionary-era tavern. Come on a weekend to enjoy samples or bottles, plus food trucks and live music on an outdoor stage.
Best Outdoor Dining
Maryland: Pirate’s Cove, Galesville
You’re practically on the dock itself when you grab an outdoor table at this longtime favorite in Anne Arundel county. Live music, a diverse menu, and a congenial crowd makes it an ideal spot to while away the hours.
Virginia: Water Street Grille, Yorktown
The brick patio overlooking Yorktown Beach and the York River behind is an ideal place to watch the comings and goings of ships in and out of the Bay. Brick-oven pastas and pizzas pair well with the 20 craft beers on tap, which always include lots of Virginia brews.
Best Crabcake
Maryland: Boatyard Bar & Grill, Annapolis
The slogan is “All killer, no filler,” and they mean it. Be warned: The fist-sized balls of jumbo lump meat, perfectly broiled and served with housemade tartar sauce, will ruin you for anyplace else.
Virginia: River Market, White Stone
This longtime caterer and market flavors their freshly-made cakes with minced scallion, then deep-fries them and serves them on a Kaiser roll to go. Or pick up some to cook at home, along with fresh-baked pie or brownies for dessert.
Best Brew Pub
Maryland: Rams Head Tavern, Annapolis
Their Fordham beer was brewed onsite until popularity outgrew capacity. Now made in Delaware in partnership with Old Dominion, it’s still the house draft—in the form of IPAs, lagers, sour, and stout—alongside a rotating cast of guest taps. Enjoy a pint in the outdoor beer garden, in the cozy basement, or in the always-buzzing main room.
Virginia: Gloucester Brewing Company, Gloucester
Brewmaster Myron Wade perfected his skills in his garage before opening this microbrewery in a former courthouse on Main Street. The Shucking Good oyster stout is brewed with local oysters, and it’s shucking delicious.
Best Bartender
Maryland: Jamie Taylor, Brian Boru Irish Restaurant and Pub, Severna Park
With the Boru team for eight years and counting, Jamie’s loyal following of regulars-turned-friends comes from his affable nature and personal service. “He remembers the things that are important to people,” says manager Heather Saffield, be it pouring your usual before you even order or participating in charity fundraisers in his time off.
Virginia: Tom Sawyer, Hole in the Wall, Grimstead
A Mathews County native, Tom has been with the restaurant since it opened, and designed their popular (and strong!) specialty cocktails. Loved by locals for his easy-to-talk-to nature, he extends that friendly vibe to visitors as well. “We get boat traffic from all over the place,” he says. “I love seeing when people come from far and wide to check us out!”
Best Out-of-the-Way Historical Restaurants with Water Views and Great Local Seafood
First place: The Wellwood, Charlestown, MD
I’m not actually choosing best and almost-best here. Rather, the order is based entirely on geographic location going north to south. So, nobody take offense. That said, the Wellwood is possibly the most interesting, if not the oldest, on my list. It began life in the 1800s as the Wellwood Club, an organization established to cultivate happiness among its members. Late in the century, it expanded to include a duck pond and dormitory (among other things) and became the Wellwood Yacht & Country Club. Among the Wellwood’s habituées were Theodore Roosevelt and Calvin Coolidge. In the 1950s, the Wellwood was purchased by the Metz family, who own it still. Now in addition to the restaurant, it includes the River Shack, where crabs are king, and docks for visiting boats. You could say they are still concentrating on happiness. This year, the Wellwood is open for inside and outside dining and the River Shack is to-go only.
Second place: The Kitty Knight House, Georgetown, MD
Georgetown, up the Sassafras River, is not exactly out of the way. But the reason I wanted to put it here is that the Kitty Knight House, which has been a popular dining spot for decades, closed several years ago and has only recently (and very happily) reopened under new owner Sueann Hall. I will not go into the whole story about Kitty Knight saving some houses and a church from the wicked Admiral Cockburn during the War of 1812, but rather leave it to you to discover, preferably as you sit out on the porch overlooking the Sassafras, sipping a nice oaky Chardonnay while waiting for your fresh rockfish imperial to arrive. The Kitty Knight House does not have its own docks, but you can find dockage within walking distance at several nearby marinas.
Third place: Suicide Bridge Restaurant, Secretary, MD
I don’t know how this happened, but apparently things from the 1950s now fall into the historical category. Which is handy because that’s when the Suicide Bridge Restaurant was established. It was just a tiny little place until Dale Nickerson, owner of Kool Ice & Seafood Co. in Cambridge, bought it in 1983. Now it has seating for 400 (pre-COVID-19) diners inside, an outdoor event pavilion, and two stern-wheel riverboats, which you can take from their Cabin Creek berth for a three-hour cruise on the Choptank River. The restaurant has docks for those of us with regular-sized boats, though those with deeper draft may want to anchor out and dinghy in.
Best Restaurant with Gliding Tables
Rudee’s on the Inlet Restaurant & Cabana Bar, Rudee Inlet, VA
At Rudee’s on the Inlet, I’m happy to say, the bench seats glide right along with the gliding tables in one happy coordinated motion. Otherwise it would be chaos. Sometimes it almost feels like chaos trying to get a gliding table on the restaurant’s popular outside patio. I don’t know how owner Carter Turpin came up with the idea, but it was genius. Rudee’s on the Inlet began in 1983 as a bait and tackle shop but has since morphed into restaurant, patio, and marina, housed in a replica Coast Guard station. What’s my go-to favorite here? The smoked fish dip every time!