Best Of the Bay: Food & Drink

Chesapeake Bay foodways run long and deep. Native American people have been enjoying the bounty of the Bay for centuries, evidenced by oyster middens dating as far back as 10,000 B.C. When colonists arrived in the 1600s, they brought new traditions and ingredients designed for surviving transport and feeding a colony. Trading ships brought in spices and flavors from across the globe, and enslaved people brought their African and Caribbean cooking traditions, which they infused into European cuisine. Later generations of immigrants brought their traditions, creating thriving neighborhoods like Baltimore’s Little Italy. That flavorful influx is still happening; go on a food tour today anywhere from Adams Morgan, D.C., to Richmond, Va., and you’ll taste flavors from almost every continent, cooked through a lens of local ingredients.  

What this means is that our food today is rich and layered, bringing global traditions to the lifestyle of fisheries and farming that still hold such prominence all around the region. The watermen working the crab pots off Deal Island or Crisfield, Md., will share their bounty with crab houses up and down the Bay, but you’ll also find it in a bevy of dishes: crab fried rice, southern-style fried green tomatoes, Baltimore’s classic crab spaghetti, soft-shell sushi rolls, crab curries and seafood versions of Irish shepherd’s pie. I bet you could eat crab every day for a month without ever having it as a crabcake—and the next month you could eat just crabcakes, without even scratching the surface of what’s out there.

And isn’t just the seafood. Take the rye whiskey resurgence, with distillers taking on the art that was begun in the earliest days of our country. Community-supported agriculture gained new prominence with the onset of pandemic-related supply-chain issues, and makers of all kinds are selling their goods at farmers markets. Pop-up restaurants and food halls are allowing a new crop of entrepreneur chefs to share their flavors and build up a fan base before investing in permanent storefronts. All of this is great news for anyone who loves regional food.

When you’re eating local, you’re sharing someone’s story—not just the people who grew it, caught it or cooked it, but also the people who came before them, who planted it, experimented with it, and perfected it. 

Our Best of the Bay food picks are all about that shared legacy, with reader contributions on everything from oyster bars to breweries. Yes, they are opinionated and we hope they spark lots of conversations around the table, and give you reasons to seek out more of our regional bounty.

Steak And Main

BEST LOCAL RESTAURANT: Steak & Main, North East, Md., and Hole in the Wall, Mathews Va.

Hole in the Wall

What keeps you coming back to a restaurant? Great food, yes, but there also needs to be a good vibe that lures you to linger, and a welcoming team that makes you feel at home. Our winners have it all. 

Steak and Main, set on quiant Main Street in downtown North East, Md, has something for everyone: a classic steakhouse menu (including a fantastic 21-day dry-aged ribeye), but also a raw bar with six types of oyster preparations and an extensive sushi menu. The cozy ambiance, with beautiful woodwork accents from the ceiling to the furniture, creates an atmosphere that’s homey yet special.

Located just over the mainland bridge on Gwynn’s Island, Va., Hole in the Wall Waterfront Grill offers ample views from the bright dining room and two-sided waterfront deck. The casual-comfort menu complements the scenery  with locally sourced seafood, fish baskets (grilled, fried or blackened), oysters aplenty, and a fun menu of cocktails and mocktails to make any day feel like a weekend.

The Point Crab House

BEST CRAB HOUSE: The Point Crab House and Grill, Arnold, Md. f

The perfect crab house has fresh, local crabs and plenty of places to spread out and enjoy them. At The Point, that means a restaurant with long tables and an oversized square bar with seating on four sides, and picnic tables on the side lawn. In warmer months, the windowed walls of this former warehouse fully retract, the better to drink in the views of scenic Mill Creek. Not in the mood for picking? Enjoy small plates like jumbo-lump-topped fried green tomatoes or deviled eggs; hearty crabcake sandwiches and burgers; tasty pork, fish or shrimp tacos; and save room for Bryan’s fried cornbread sundae. There’s live music most nights, and a wait on weekends. It’s worth it.

Brian Boru Restaurant and Pub

BEST BAR: Irish Restaurant Company, Annapolis

Pick just one favorite bar? We can’t, and neither could our readers. Thankfully, the winning Irish Restaurant Group has four. Galway Bay Irish Restaurant and Pub is a cozy Irish pub with an award-winning whiskey list, situated on beautiful Maryland Avenue in downtown Annapolis.
Brian Boru Restaurant and Pub is a friendly hangout for families and friends, located in Severna Park. Killarney House is an Old World, wood-paneled retreat in rural Davidsonville. Pirate’s Cove Restaurant and Dock Bar in Galesville overlooks the West River, easily accessible by boat or car. They all feature fantastic food (including Irish favorites like shepherd’s pie at the pubs, and plentiful seafood at the dock bar), plus great live music and genial Irish hospitality.

BEST DOCK AND DINE: Pirates Cove, Galesville, Md., and Hole in the Wall Waterfront Grill, Mathews, Va. 

Boaters love tradition, and both of these winners from last year have the same recipe for success. First is a great location: Hole in the Wall is set on Gwynn’s Island, where the Piankatank River meets the Bay, while Pirates Cove is on the West River, convenient to Annapolis. Add in ample docking space, wide open-air decks for waterside dining, fresh food with something for everyone, and you get that last piece: convivial crowds, made up of locals and boaters passing through for an afternoon or weekend.; 

Lyon Rum

BEST DISTILLERY: Lyon Rum, St. Michaels

What’s not to love about a distillery and tasting room, set in an historic mill in the heart of St. Michaels? Repeat winner Lyon Rum is going to be even better when it reopens for tastings in fall 2022 after a months-long renovation. Meanwhile, check out our runners-up. Set in D.C.’s Ivy City neighborhood, Green Hat Distillery’s bar and gin garden is open on weekends, offering tours, flights and cocktails made with their botanical-infused gin. 

In ESVA, Cape Charles Distillery’s retro-eclectic setting is the perfect place to sip Virginia-grown bourbon, whiskey, vodka, and more, paired with oysters from nearby farms.; greenhatgin. com;

BEST WINERY: Running Hare Vineyard, Prince Frederick, Md., and Williamsburg Winery, Williamsburg, Va.

The arched windows, tile roof, elegant cypress trees and surrounding vineyards may say Tuscany, but this beauty of a winery is in Southern Maryland’s Calvert County. Running Hare offers something for everyone, with wines (think popular varietals like malbec, sangiovese, chardonnay, and rose) as well as wide selection of local craft beers on draft at in their Southern Maryland Biergarten. There’s live music every weekend, food trucks for snacking, and even wine slushees to beat the heat on summer days.

Award-winning Williamsburg Winery has 50 acres of vineyards set on original Colonial-deeded land. Enjoy the views from the bi-level deck, soak up the sun on the flagstone patio, add farm-to-table plates from Archer Tavern, or book a room at the inn and make a weekend of it.

BEST BREWERY: Forward Brewing, Annapolis, and That Damn Mary Brewing Company, Hayes, Va.

Forward Brewing opened in the Eastport section of Annapolis during the pandemic and quickly became a superstar, serving window-side from their nano brewery. Nowadays you can also enjoy their tasty creations inside, paired with snacks like pretzel pizza and impossible meat sliders. Their Kolsch-style Annapolis Boat is perfect for a day on a, you guessed it, or try a double IPA, barrel-aged Belgian, or sour ale. 

Craft brewing has long been a male business, but not in Gloucester County, where owner and self-proclaimed overlord MJ (Mary Jane) Anderson has been brewing beer since 2018. Hit their cheery red barn for an ever-changing selecting of beers, brewed onsite to be both delicious and sustainably produced, and catch them at music festivals all around Tidewater Virginia. (Don’t miss the fantastic beer descriptions on their website; if they don’t make you laugh out loud, you obviously need more beer.) 

Forward Brewing

BEST FARMERS MARKET: Chestertown Farmers Market, Md., and Smithfield Farmers Market, Va. 

Farmer’s markets are the original grocery store, a centralized place where farmers can sell their wares directly to their customers, no middleman needed. The best markets add in crafts vendors, specialty goods, and family-friendly entertainment. The Chestertown Market, based at Fountain Park on historic High Street, is open every Saturday, 8 a.m. to noon, through October.  The Smithfield Farmers Market takes place every Saturday from 9 a.m. until noon, from March through October, in a lot just off Main Street. Both offer special themed markets throughout the year, and holiday markets in November and December. Alongside farm-fresh meats and produce you’ll find specialty purveyors selling sauces, baked goods and more; craftspeople with jewelry, leatherwork, stained glass; and live music, giving the morning a festival feel.; smithfield



Best All-Purpose Farm to Table: Denson’s Chesapeake Bay Farm to Table Oyster Bar,
Food Truck & Catering I Colonial Beach, Va.

Rocky Denson and his wife, Blaire, take local seriously, from Northern Neck produce and special meats to oysters, crabs and fish from the Potomac and the Rappahannock, plus local wines and craft beers. Menus change with seasonal opportunities and the creative flair of Rocky’s imagination, built on the firm foundation of this third-generation family business. Check the current menu on the Denson’s Facebook page, order takeout, eat at the outdoor cafe, look for their food truck Chesapeake Beast, or schedule catering featuring the best food and drink the Northern Neck has to offer.
-John Page Williams

Best Open-Air Oyster Bar: Merrior Tasting Room I Topping, Va.

This alfresco eatery is deceptively simple. Order at the window, return for your plate when your name is called, and enjoy it at a patio table overlooking the very waters where the oysters you’re eating were raised. The briny air, view of weathered oyster boats, and sound of lapping waves only enhances the flavors of the menu, which features raw oysters, roasted oysters and oysters Rockefeller, as well as plates like red pepper crab soup, scallops in brown butter, and the craveworthy stuffin muffin: oyster stuffing with bacon and peppercorn cream sauce.

Best Casual Oyster Bar: The Local Oyster I Baltimore

Nineteenth-century oyster bars were unpretentious, unfussy establishments, the opposite of the fine-dining reputation they developed later on. The Local Oyster harkens back to that earlier era. At their two food hall locations—one at Baltimore’s Mount Vernon Marketplace, one at Arlington’s Quarter Market, and a third location coming to Baltimore’s Locust Point this summer—the vibe is cheery and accessible with long counters and communal tables, a slew of craft beer on tap and fresh bivalves, including ones grown at their own farm. Bonus points for $1 oysters when it rains.

BEST SOUL FOOD RESTAURANT: Porter Soul I Cambridge Md.

Soul food is as much a Chesapeake Bay tradition as crab feasts and Old Bay. In Cambridge,  Porter Soul’s “soul food with an attitude” serves up a variety of delicious dishes to please both the down-home traditionalist and anyone looking for the taste of soul with dishes like collard greens, succotash, turkey wings, and “oxtails and candied yams from heaven.” Those of us who grew up on the dessert doubleheader of pound cake and sweet potato pie will not be able to resist Porter Soul’s twist on the flavor combination; their sweet potato pound cake is a thick slice of melt-in-your-mouth perfection and an automatic to-go addition to any meal I order. 443-225-5175 or find them on Facebook.


If you’re convinced that vegan/vegetarianism is synonymous with slivers of carrots, a few stalks of celery and a tall green drink, Denton’s Earth Tones Cafe will quickly change your mind. Try a silky soup or a sweet and savory toast like the avocado with egg, avocado and sharp cheese, or a new twist on the classic PBJ, crafted from peanut butter, strawberry preserves and lemon jam—the flavors burst in your mouth. Along with daytime deliciousness, Earth Tones offers nighttime entertainment in the form of live music, a dinner menu, and selections from the beer, wine, and cocktail list.
-Niambi Davis


The Exmore Diner is a hidden mecca for local seafood and Eastern Shore cuisine. Peas and dumplings, turnip greens and sweet potatoes are often on the “sides” menu, but if you keep careful watch in the summertime you can sample one of the best fish to come out of the Bay: swelling toads (Sphoeroides maculatus), also called pufferfish. Swelling toads are the Bay’s superior answer to chicken wings. They fry up crisp and light, and the tail serves as a convenient handle to nibble the tender white meat along a single, central bone. The Exmore Diner keeps Eastern Shore culinary traditions like swelling toads alive and is worth a special trip. Check their Facebook page for the daily menu.
-Robert Gustafson

Chesapeake Restaurant I Dredge, Irvington, Va. 

Chef Bryan Byrd hails from Virginia but spent time in Key West before returning home to open his award-winning food truck, Byrd’s Seafood Co., and then his acclaimed restaurant, tucked in a cute bungalow in Irvington. Island flavors are infused in everything from slow-roasted Cuban pork and half-baked oysters topped with chorizo, cheddar jack, and a spicy verde sauce to the Key Lime tartar sauce that accompanies blackened mahi and shrimp. Best yet, he sources from local purveyors, including their family farm, located just north in Lively, Va.
-Susan Moynihan