Exploring Chesapeake Bay: A Culinary Adventure in Maryland
In James Michener’s epic 1978 novel “Chesapeake,” a 16th-century Susquehannock named Pentaquod rows across the titular bay and wonders at “the immensity of this water, the way the fish jumped as if they were eager to be caught and tasted.” Nearly 500 years later, the Chesapeake Bay—an abundant estuary bisecting the state of Maryland—still ranks among the country’s natural wonders and serves as the source of one of its most underappreciated cuisines.
About 30 miles outside the nation’s capital, you encounter the Eastern Shore, where rivers and inlets scallop the bay’s edge, contributing to a shoreline longer than all of Florida’s. Some waterfront towns retain their roots in fishing, boatbuilding, and canning. Until recently, however, the ecosystem Michener described faced a dire threat. By the 1970s, industrial farming and deforestation polluted the area, drastically depleting marine species. Thanks to a decades-long cleanup effort, this once-damaged body of water is beginning to thrive again.
Moreover, as the bay is replenished, its culinary offerings are reaching a new audience. Chesapeake cuisine encompasses much more than just steamed crab and Old Bay—even though they are widely loved and delicious. The culinary offerings trace back to enduring indigenous influences, as well as recipes from enslaved Africans and seafaring settlers. Today, influential chefs, including Spike Gjerde of Woodberry Kitchen in Baltimore and Jeremiah Langhorne at Dabney in D.C., are sharing the Chesapeake culinary gospel.
Last October, I traveled to the area to immerse myself in the beauty and flavors of Chesapeake Bay.
Friday: Culinary Ventures in Annapolis
I began my adventure in Annapolis, Maryland, a must-visit destination on any journey to eastern Maryland. This delightful city offers more than just the famous naval academy; history surrounds you with colonial-era taverns, 19th-century churches, and the statehouse where the Treaty of Paris was ratified. However, the city is also undergoing a transformation, with stylish, newly opened restaurants lining the red-brick Main Street leading to Annapolis Harbor.
I stopped for lunch at Preserve, a restaurant and pickling operation led by Jeremy Hoffman, a former chef at New York City’s Per Se, and his wife, Michelle, a former employee of Union Square Café. The menu reflects Maryland’s culinary heritage with a modern twist: dishes like fish-and-chips featuring tempura catfish and buffalo-style soft-shell crab. Following my meal, I wandered to the waterfront and discovered the 160-year-old Market House, which hosts a new food hall and grocery filled with local goods such as cider, seasoning mixes, and freshly harvested oysters.
Nearby, the vibrant Arts District showcases the best galleries in the city and features the delightful Sailor Oyster Bar. I enjoyed an afternoon treat of crudo and smoked sardines paired with buttered bread. At the heart of the district is the new Graduate Annapolis, an ideal place to stay. The hotel perfectly encapsulates the essence of this college town, with navy signal flags adorning its lobby and a color scheme inspired by the iconic Chesapeake blue crab.
The Graduate is perfectly situated for exploring Annapolis’s many attractions, the most delicious of which is Flamant, a new restaurant in a charming clapboard bungalow nestled in a quiet residential neighborhood. Belgian-born chef Frederik De Pue, formerly of Washington, D.C.’s Table, crafts modern iterations of Flemish classics. I stopped by as rain began to fall and warmed up with a glass of Riesling and a cozy veal stew accompanied by traditional Belgian pommes frites.
Saturday: Discovering the Eastern Shore
Crossing the Chesapeake Bay Bridge brings you to the Eastern Shore of Maryland—a portion of the Delmarva Peninsula that extends down to Virginia’s easternmost counties. Many visitors find the drive daunting due to notorious traffic backups, but there is a more scenic option. The Inn at Perry Cabin, my destination for the night, offers a delightful alternative. On a bright morning, I traveled from Annapolis to Pier 7 in nearby Edgewater to catch a transfer across the bay on the inn’s 55-foot yacht.
With champagne in hand, I relished the captain’s tales of the Chesapeake’s history and geography—complete with descriptions of crumbling lighthouses, sandy shoals, and hidden trenches. Below the boat, marine life flourished, showcasing the ecosystem’s gradual restoration, including crabs, rockfish, oysters, dolphins, and even the occasional shark.
After about an hour, we docked at the Miles River, a tranquil tributary of the bay. The Perry Cabin stands as a stately presence on this serene inlet. Originally built by a wealthy navy veteran of the War of 1812 and named for his commander, Commodore Oliver Hazard Perry, the property was transformed into a hotel in 1980. Despite several expansions—most notably a golf course designed by renowned architect Pete Dye—historical elements, including a bust of Commodore Perry in the lobby, remain intact.
Just off the property lies St. Michaels, the setting for Michener’s book. This bustling port has played a vital role in Maryland’s history since the mid-1600s. Its shipyards were key during the War of 1812, and Frederick Douglass covertly taught his fellow enslaved people to read and write in a house just off Talbot Street.
St. Michaels also serves as a gateway to the region’s rich cuisine and culture. At Stars, Perry Cabin’s formal dining area, chef Gregory Wiener emphasizes Chesapeake seafood and ingredients sourced from the hotel garden. For those seeking a closer farm-to-table experience, consider arranging a rosé-and-oyster sailing with the boating concierge. Additionally, Eastern Shore native chef Doug Stewart offers comfort food classics like crab cakes and succotash at Bistro St. Michaels, an inviting dining spot set within a century-old house.
In St. Michaels, happy hour revolves around the Old Mill District, a collection of transformed warehouses just a mile from the inn. I stopped for a refreshing drink at Lyon Distilling Co., established in 2012 by former bartender Jaime Windon, credited with revitalizing Maryland rye. However, her personal favorite spirit remains rum, the first ever distilled in Maryland.
Sunday: Turning to the Towns of Eastern Shore
At Perry Cabin, visitors face the delightful dilemma of deciding which direction to explore. Perhaps a trip to Easton, recognized as the restaurant heart of the area? The culinary team at local favorite Bas Rouge has opened a new eatery known as Stewart, featuring an impressive menu of Scotch and a Parisian-inspired dessert shop called Bonheur. Alternatively, visitors could venture to the islands, including Tilghman for fresh oysters and crabs, Assateague to see wild horses, or Smith, known for its famed layer cake.
Eventually, I chose to utilize the inn’s bike-rental service, riding to nearby Bellevue to catch a boat across the Tred Avon River. The Oxford-Bellevue Ferry has been operational since 1683 and was saved from extinction by a local couple in 2002. The trip, brimming with misty vistas and tranquil waters reflecting flocks of great blue herons, costs only $3 for a round-trip ticket.
Upon arrival in Oxford, one of the earliest permanent settlements on the Eastern Shore, the region’s maritime history felt palpable. A visit to the quaint Oxford Museum provides insights into the canneries, shipyards, and oyster beds that sustained this town for centuries.
To savor the humble origins of Maryland cuisine, I dined at the 300-year-old Robert Morris Inn. Sitting by the fireside in its brick-walled, timber-beamed tavern, I indulged in local classics like fried seafood, oyster pie, and oversized crab cakes filled with sweet meat. It was a simple yet hearty feast, providing a true taste of the spirit of the Chesapeake on a plate.
A version of this story first appeared in the November 2019 issue of iBestTravel under the headline Bay Watch. Inn at Perry Cabin provided support for the reporting of this story.
Correction: An earlier version of this story incorrectly identified Bas Rouge, in Easton, as having been nominated for a James Beard Award. We regret the error.
