A Taste of Summer at the Eastern Shore

Quaint towns, fresh seafood, family sailing—it's all just 90 minutes from D.C.

For many Washingtonians, summer begins the moment their car tires touch the Chesapeake Bay Bridge. On the western side of the bridge lie reminders of work and school-year schedules. On the other end of the 4.3-mile span, the rural Eastern Shore beckons with sailboats, gracious Victorian homes and lazy vacation days, where the only pressing thing on the to-do list is deciding which seafood restaurant to try each day.

Although “Eastern Shore” can refer to a broad area encompassing several counties and the entire east side of the Chesapeake Bay in Maryland, my family and I focus on Talbot County—which was formally established in 1661—for a weekend day trip. There, just an hour-and-a-half drive from D.C., we can experience a microcosm of what makes the Eastern Shore a quintessential summer getaway.

Of course, a successful family trip involves some compromise. OK, a lot of compromise. I want to stop at the Saturday farmers market in the town of Easton, the commercial hub of Talbot—pronounced TALL-but—County. My husband would like nothing better than to nurse a cold craft beer at Eastern Shore Brewing in St. Michaels. My three kids—ages 11, 7 and 4—want to head directly to the water.

It’s a hot, humid day so we all eventually agree: water. We drive to St. Michaels, past cute boutiques along Talbot Street before reaching the Chesapeake Bay Maritime Museum. At the dock of the waterside open-air site, we board a working skipjack, the H.M. Krentz, for a two-hour sail on the bay captained by Ed Farley.

Lighthouse at the Chesapeake Bay Maritime Museum

Captain Farley has been harvesting oysters here during the fall/winter season for 45 years. A few years back, he also began offering leisure cruises during the summer tourist season.

With a dapper white moustache and an easygoing manner, he is a wealth of information about the history and current state of Chesapeake Bay oystering. You wouldn’t know it from the ubiquity of the crab on Maryland bumper stickers and logos, but oysters were the state’s claim to fame in the late 19th century and well into the mid-20th.

Farley explains that disease devastated the oyster beds in 1983. Thanks to harvest management, oyster reef restoration and disease prevention measures, the bivalves have made a comeback, but not yet to pre-1983 levels.

Back on land, we explore the Chesapeake Bay Maritime Museum, which is full of hands-on exhibits and historic boats. We climb to the top of the 1879 lighthouse that used to sit in the Hooper Strait, and we peer into a stove pot to see the type of fare lighthouse keepers once ate—boiled potatoes and biscuits, by the looks of it. We pause to watch conservators restore an 1889 bugeye—a predecessor to the skipjack.

Lunch is at buzzing Ava’s Pizzeria, where I order a refreshing salad of arugula, goat cheese, strawberries and candied walnuts, and the kids share a thin-crust cheese pizza and a juicy chicken parmesan. Just down the street at 30-year-old Justine’s ice cream parlor, we sit on chairs on the sidewalk and lick scoops of mint chocolate chip, pistachio, caramel crunch and cookies n’ cream. Justine’s also whips up shakes in flavors from creamsicle to key lime. An employee comes out and gives us a bottle of water.

“It’s hot out today,” he explained. “We’re all family.”

One of many choices for ice cream in Talbot County

I wonder, isn’t it time for some shopping yet? But the kids are adamant: more water, please, so we get back on the road toward the Oxford-Bellevue car ferry. Along the way, we stop at Rise Up Coffee Roasters, a drive-up kiosk in a strip mall parking lot offering strong espressos and smoothies.

As we pull onto the ferry for the 20-minute crossing of the Tred Avon River, I try to tell the kids that this may be America’s oldest privately owned ferry route. But they’re too busy jumping up and down in excitement that our minivan is actually on a boat. My youngest stands at the front of the ferry and does her best Jack-and-Rose-on-the-Titanic impression, arms spread out, wind whipping her curly hair. “My heart will go on!” she exclaims.

Oxford-Bellevue car ferry

Oxford is another typically quiet and quaint Eastern Shore town with more cute stores I can’t browse through, including an indie bookshop—Mystery Loves Company Booksellers—and a new home store—Yacht and Home—as well as another classic ice cream shop, Scottish Highland Creamery. A new park trail is perfect for walking and biking.

In the end, we all agree that there’s only one way to conclude our Eastern Shore getaway: sitting by the bay eating seafood. We head back to St. Michaels, where we belly up to wooden picnic tables at Crab Claw. My husband and I dig into half a dozen blue crabs spiced with Old Bay, while the kids chow down on crab cakes, hush puppies and corn on the cob.

Steamed blue crab

Yup, tastes like summer.