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With Memorial Day weekend just around the corner, I packed my bag and drove east, following an 80-mile trail trod for decades by fellow Washington residents seeking quieter seasonal destinations. After crossing the Chesapeake Bay Bridge and heading south on windy back roads, I finally disembarked in St. Michaels, Maryland, a waterfront destination often celebrated as one of the crown jewels of Maryland’s East Coast.
Tucked away in the brackish wetlands of the Chesapeake Bay, the town of St. Michaels has preserved the scenery of its 19th-century past, when the shipbuilding industry was dominant and oyster and crab crops poured out of the docks in abundance, making small fortunes for locals. merchants .
Today, its transformation into a vacation resort is nearly complete, but the lasting impression of its maritime roots and touches of wealth from its heyday have made it stand out even in a part of Maryland rich in small towns reminiscent of the early beginning of the United States. year. In a short three days, I came across a wealth of early American architecture and a wealth of opportunities to explore the Chesapeake landscape by land and water.
My first night, I arrived on the short main street of St. Michaels, hungry for dinner, and found that most of the restaurants in town were mostly bistros, steakhouses, and seafood-focused bar-and-grills. A fine showcase of Chesapeake Bay seafood – fresh oysters, soft-shell crab and blackened rockfish – already drew crowds to favorite spots such as the crab claw and Terrible Arthur’s† But in the end I set my sights on lista vibrant, fresh location that opened in 2021, during the pandemic, and operates out of the unusually modern city Wildset Hotel†
Instead of the classic Maryland crab cakes that are ubiquitous in the area, I’ve indulged in blue crab rangoon, made with a light grainy ricotta instead of cream cheese and subtle, sweet crab meat. For a different twist on local fare, I tried Ruse’s light and citrusy scallop ceviche, which was served on a tostada shell instead of the traditional half shell.
Many of the city’s more stately mansions now function as bed-and-breakfasts, and as dusk fell I went to the George Brooks House, a Civil War era mansion on a quiet eight-acre lot. I laid my belongings on the ornate four-poster bed facing a fireplace in my room and stepped through a private side door to the back porch of the house to take in the golden hour lighting hitting the backyard and pool.
The next morning, while I ate a homemade breakfast of French toast stuffed with honey-crispy apples, the owner and innkeeper, Will Workman, treated me and other guests to local lore from the early 2000s, when St. Michaels became a popular retreat for senior members. of the George W. Bush administration.
During those years, several top White House officials—including former Vice President, Dick Cheney, and Secretary of Defense, Donald H. Rumsfeld—turned the orbit of the White House. started picking up millions of estates† Taking advantage of the quiet seclusion of the city, still within reach of Washington, they began to turn St. Michaels into an unofficial weekend retreat.
On one of those weekends, he said, the Secret Service motorcade protecting Mr. Cheney encountered St. Michaels’ traditional St. Patrick’s Day festivities, with locals closing the main road to race shopping carts down the street. As the story progressed, the city’s leaders and police chief refused to clear the way, in a display of local pride and independence, forcing the former vice president’s motorcade to wait.
After breakfast, I ventured just outside the city limits and crossed the drawbridge to Tilghman Island, which lies at the end of the peninsula west of St. Michaels. Rental bikes are available in town and the drive to the island, be it by bike or car, takes a winding path past a narrow headland with secret beaches and stunning views of the bay on either side.
Like most of Talbot County and surrounding areas, the richly biodiverse Tilghman Island is a popular bird watching destination. When I approached Black Walnut Point at the tip of the island, a pair of bald eagles made low passes overhead, and osprey nests were visible along the shore at regular intervals. The walk to the point follows the shoreline until the road ends, but for those wanting to venture further into the bay, outfitters on Tilghman rent out everything from paddleboards and kayaks to sailboats and jet skis.
I have reserved my last afternoon for the Historic District of St. Michael† In less than an hour, I walked past nearly two dozen mansions and churches, stopping at each location and taking in the impressive spectrum of Victorian, Italianate, and Federal architecture. Some of the oldest buildings in the area date back to the 18th century and survived the town’s minor role in the War of 1812, in which it was twice raided by British soldiers during their campaign in the Chesapeake.
Beaten down by the summer heat, I gave in and went to Justine’s ice cream parlor, where a dizzying menu of milkshakes takes up an entire wall. With ice creams like rum raisins and spumoni, or rainbow sorbet and orange juice, Justine’s combines a seemingly infinite number of shakes and shake-adjacent creations that blinded visitors for 35 years.
While marinas and boat launches line the shoreline throughout the region, the marina in St. Michaels benefits from the presence of the Chesapeake Bay Maritime Museumwhich host a floating fleet of preserved historic shipssuch as crab dredgers and Chesapeake log canoes, as well as a replica of a large ship from the colonial era.
The view of these classic ships against the modern backdrop of powerboats, waterfront restaurants and tour boat companies was shocking. Then somewhere between a cluster of small yachts and what appeared to be a functional one skipjack (an old wooden commercial sloop, now used for private charters), I came across a boat with the Talbot County seal. The Latin words underneath, “tempus praeteritum et futurum,” seemed to offer an explanation: “time, past, and future.”
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