Dorchester County is More Than Just a Pit Stop on the Way to Ocean City

If you can’t judge a book by its cover, surely you can’t gauge a place by seeing it from the highway. Take Dorchester County. Beachgoers use the scant 16 miles of Route 50 that pass through Dorchester on their way to Ocean City. Other travelers barely look around as they head straight for the Hyatt Regency Chesapeake Bay, the self-contained luxury golf resort, marina, beach, and spa located in its biggest town on the banks of the Choptank River. But there’s more to this roughly heart-shaped, indelibly Eastern Shore province about an hour and a half from Baltimore.

First, there’s Cambridge, Dorchester’s epicenter. Established in 1684, the small “city” most recently reimagined itself some 25 years ago, when revitalization began downtown and the Hyatt came along.

Today, thanks to a lively arts and entertainment district, Cambridge is a destination unto itself. But don’t stop there. To discover what makes Dorchester “the Heart of Chesapeake Country,” drive south on the blue highways to explore the county’s lovely marshy lowlands and tidal peninsulas that barely tread water but pulse with wildlife, unforgettable scenery, and the allure of tiny watermen’s villages. The residents’ resilient Eastern Shore way of life is disinclined to change, even as the landscape around them does in the midst of sea-level rise and a mutating climate.

I confess that I’m smitten. In trips over the years, I’ve become enchanted by Dorchester’s penchant for preserving deeply rooted Chesapeake traditions. I’ve listened to an old-school taxidermist explain his wizardly art. Visited an aquaculture nursery bringing new hope to a dying town. Kayaked an avian oasis—Blackwater National Wildlife Refuge—nicknamed “the Everglades of the North.”

Most memorably, I once was tapped to judge a muskrat-cooking contest, despite never having tasted one. In Dorchester, where family is everything and muskrats symbolize what locals call “the brackish life,” I had one chief qualification to help arbitrate this cherished competition: I wasn’t related to any of the contestants.

Chunky, semi-aquatic rodents prized for their pelts, muskrats (aka “marsh rabbits”) are particularly dear to South Dorchester Countians. In these parts, the animals are the centerpiece of a decades-old winter festival, the National Outdoor Show in Church Creek—reason enough to go this time of year. From its humble beginnings in 1938, it has evolved into a celebration of rural rituals. Come February’s final Friday and Saturday, the South Dorchester School’s classrooms and corridors overflow with vendors hawking an alphabet’s worth of local merch and services.

On my first visit, displays ranged from Albert’s Roadkill Creations’ vibrant skeletal art to the leathery muskrat pelts that Zander Fur Company buys locally and sells overseas to hat-makers. Long-held local skills are honored in the gymnasium and outdoors where men, women, teenagers, and senior citizens vie in trap setting, oyster shucking, trotline baiting, and log sawing, as well as goose, duck, and turkey calling. In the cafeteria, diners nosh on fresh crab-cake sandwiches, savory oyster fritters, cups of steaming Maryland crab soup, and—for a limited time Saturday—locally sourced muskrat, a one-time staple of Dorchester diets. The ’rat-reluctant can sample small pieces for a dollar. (While opinions vary, I think the meat tastes like beef liver.)

The Outdoor Show is highlighted by successive beauty-and-beast competitions. On opening night, young ladies compete in the coveted Miss Outdoors pageant. The following evening, the World Championship Muskrat Skinning Contest’s time-honored rivalry is open to nearly anyone skilled with a blade. Junior skinners compete first before a packed gymnasium, followed by contestants who must swiftly and skillfully separate fur from flesh. It may sound off-putting, but you can’t help but be impressed. Just be forewarned: There will be blood—and a pervasive musky aroma evocative of swamps.

“It’s so back in time—it makes me very proud,” says Dorchester native Susan Meredith of the Outdoor Show. Her family operates Blackwater Adventures, which runs guided kayak, bike, and fishing excursions in and around Dorchester’s crown jewel, the 32,000-acre Blackwater National Wildlife Refuge.

Generations of Merediths have called Dorchester home, and the couple owns the historic Bucktown General Store, where hometown heroine Harriet Tubman suffered a severe injury while protecting a fellow enslaved person. (The incident was said to give her prophetic visions before she became a leader of the Underground Railroad.) Just down the road, Gov. Wes Moore unveiled a historical marker last June dedicated to the birthplace of this famed abolitionist.

When Meredith isn’t guiding guests or exploring her favorite kayaking water, the Transquaking River outside of Blackwater, she likes to frequent other family businesses. To throw a line, check out Captain Phil Gootee Fishing Charters and Tours in Church Creek, which also offers twilight cruises showcasing some of Dorchester’s scenic shoreline. To throw back some wine, visit Layton’s Chance Vineyard & Winery on a family farm in Vienna, with a large tasting room and summer concerts.

For seafood, Meredith recommends a pair of iconic Dorchester businesses. For more than a century, the J.M. Clayton Company has processed, packed, and sold top-quality crab meat from its waterfront building in Cambridge. At the shop office, pick up fresh jumbo lump crab meat for carry-out to cook at home. Then the Suicide Bridge Restaurant in Hurlock—“great place, terrible name,” Meredith says—features a seafood-centric menu (rockfish, flounder, oysters, soft shells, crab cakes, etc.) plus a legendary backstory. Several people have met their deaths here, but the dramatic rescue of one woman from icy Cabin Creek is still told in local word and song.

With attractions like the acclaimed Dorchester Center for the Arts, busy community spaces like the renovated Packing House, and the Harriet Tubman “Beacon of Hope” statue, Cambridge has become a comfortable fit for the creatively inclined. Artist Michael Rosato arrived 25 years ago by way of New York City and Washington, D.C. He’s best known for the city’s iconic mural, “Take My Hand,” a powerful trompe l’oeil painting on the Harriet Tubman Museum and Educational Center near his downtown studio. In it, Tubman’s right hand appears to reach through a brick wall, inviting viewers to escape with her into the marshes.

“I wanted people to ask themselves, ‘Would I have the courage to come back?’,” says Rosato—as Tubman did more than a dozen times to rescue enslaved friends and family.

He and his wife love to hike and kayak in Blackwater. In Cambridge, Rosato’s favorite haunts include Vintage 414, a women-run wine bar next door to his studio; Bombay Social, an Indian restaurant and bar; and Black Water Bakery, a coffeehouse serving breakfast and lunch. When shopping, he heads for Simmons Center Market, a fourth-generation, family-owned, Cambridge grocery store specializing in fresh-cut meats and seasonal flowers (“It’s like walking into a time warp”), and Emily’s Produce, a full-service market in Cambridge (“Dorchester’s Whole Foods”) that sprang from an honor-system roadside stand.

From their Cambridge home, one-time Baltimore editor Jim Duffy and his photographer wife, Jill Jasuta, operate Secrets of the Eastern Shore, a website that champions the Delmarva Peninsula. The couple moved from Charm City more than two decades ago and now use their respective talents to document the people, places, and history of their adopted home. Jasuta’s ideal Dorchester day? A morning hike at Blackwater or Robinson Neck Preserve, a hidden gem on Taylors Island (“very wet; boots are crucial”). Lunch at Boats & Hose next to the Taylors Island fire station (“snakehead bites, soft-shell crab sandwich, Orange Crush”). Then to Cambridge for gallery-hopping and shopping at Laughing Lotus (handmade goods and local artworks), Main Street Gallery (artist-owned cooperative showcasing juried works), and Sunnyside Shop (fair-trade clothing, jewelry, and more).

In addition to Vintage 414, Jasuta has dinner at The Dive Club (“for the immersive maritime experience and a strong rum drink”), run by local beer legends RaR Brewing, whose taproom sits across the street, or Christopher’s Corner (“a little fancier, somewhat goth atmosphere”). Cocktails are a hit at nearby Blue Ruin.

Among other books, Duffy has authored travel guides, including his two-volume Eastern Shore Road Trips. To his wife’s in-town dining choices, he adds Old Salty’s Restaurant on remote Hoopers Island. “The long and gorgeous drive is always worth it,” he says. “Leave extra time to wander Smithville Road.”

This time of year, look for hordes of wintering waterfowl and the occasional bald eagle. If you want to eat where the locals do, he suggests Cindy’s Kitchen. The homestyle Cambridge eatery serves Shore comfort food (catfish and corn bread, fried oysters, meatloaf, stewed tomatoes, blueberry pie) to patrons whose pickup trucks, police cruisers, and occasional tractor or combine fill the parking lot. Table conversation often covers hunting, fishing, and crops. Décor is early farm implements.

There’s also Woolford Store, a country store-cum-hunting-and-fishing emporium where you can chow on breakfast sandwiches surrounded by snakehead lures and sika deer-hunting accessories. These small members of the elk family were introduced to the Eastern Shore from Asia and survive in considerable numbers in southern Dorchester. In addition to Blackwater, other must-visit destinations include the Harriet Tubman Underground Railroad National Park in Church Creek—a highlight of the Tubman Byway’s self-guided driving tour through Maryland, Delaware, and Pennsylvania.

Local favorites are scattered smack dab along Route 50, too. Come April, there’s no better place to enjoy a crab feast than Ocean Odyssey. Run by a longtime waterman’s family, it’s only open in season when the beloved blue shells are hauled straight from the Choptank and steamed fresh to order.

Meanwhile, the sprinkles-studded pink doughnut painted atop Bay Country Bakery telegraphs to passing drivers the café’s signature sweets, which are fresh baked every morning. For a kick of caffeine, Rise Up Coffee is a short distance away. Known for its organic brews and top-notch burritos, the locally owned coffee roastery makes the perfect pit stop to fuel your drive home.