Eastern Shore, Maryland

The best thing about this column is that it makes me get up and go. While all my road trips are day trips—usually within a few hours’ drive—I’ve visited towns, cities, and villages I otherwise might have missed. On my trips, I get a little history lesson, meet new people, and eat like the locals eat. I love it, and my coterie of ride-along companions love it too.

Our most recent journey was to Maryland’s Eastern Shore. I always thought it was a fancy-Dan area, upper-crusty and elite, maybe because of its proximity to Washington, Annapolis, and Virginia. Instead, as the guidebook suggests, I found “a patchwork landscape of eclectic small towns” along the rivers and creeks and that feed into the Chesapeake Bay. And they all have vastly different personalities.

Our first stop was Easton, a sophisticated town known for its lively arts scene. With both pride and modesty, Easton calls itself “the eighth best small town in America,” and I wouldn’t disagree. The Quaker enclave was established in 1710. Its leafy streets are lined with Colonial, Victorian, Federal, and Georgian-style homes. And it seems there’s a beautifully maintained park around every corner.

My pal Jodee and I stole into the Gardens of the Talbot Historical Society—I say “stole” because clearly there was an outdoor wedding planned for that day. But we couldn’t resist this beautiful acre, with its terraced shade garden, wrought-iron gates, and brick walkways. Butterflies sailed all around, and the air was rich with the aroma of oakleaf hydrangeas, roses, and lilies of the valley.

I was frankly moved to see a row of tall foxglove and wax-leaf Ligustrum—they grew in profusion around my childhood home, but I’ve seldom seen them since. For me, catching those scents was like rocketing back in time.

We continued our walking tour and encountered a friendly Eastoner named Richard who was puttering around in his yard. We asked him what sights to see, and he gave us a Cliff’s Notes history of both Easton and Talbot County, especially their roles in Civil War history. Abolitionist Frederick Douglass grew up nearby and used to walk miles each day with his mother to work on a local plantation. There’s a life-sized statue of Douglass at the Easton Courthouse, juxtaposed with a Confederate States of America monument to the Talbot Boys, who fought and died for the South (as you can imagine, there’s an ongoing debate about whether to relocate the latter).

We also saw a neighborhood called The Hill, established by free blacks in the 1790s, and thought to be the oldest African-American community in the nation. If you can, make time to visit Harriet Tubman Underground Railroad State Park in Church Creek, about 30 miles south.

Richard also advised us to stop by the Academy Art Museum downtown. Its permanent collection includes works by Goya, Cezanne, Chagall, Picasso, Miro, Cassatt, Man Ray, Rauschenberg—the names alone are enough to make an art lover swoon. Also noteworthy is the 1920s Avalon Theater, a spectacular Art Deco palace with leaded glass doors, rich red carpet and upholstery, brass fixtures, and a gilded proscenium. It offers theater, music, book signings—the works. No wonder they call this town the Cultural Capital of the Eastern Shore.

It wasn’t quite noon when we stopped for brunch at the Tidewater Inn. The weather was fine, so we chose to sit on the terrace. First on tap was a mimosa for Jodee and a blueberry lemonade for me, then we had a simply dreamy meal. I ordered Caesar salad and a thick brown cream of crab soup, served with oyster crackers and a decanter of sherry. Jodee had the Delmarva omelet, also with crab, plus Virginia ham, spinach, and cheddar cheese. Next time we’ll have to try the inn’s famous Elvis Waffle, made with peanut butter, bananas, and Vermont maple syrup.

After brunch, we headed down the road to bustling St. Michael’s Island. Named for the archangel, it’s the oldest community in Talbot County, a family- and tourist-friendly place rich in maritime history. One popular attraction here is the Patriot, a replica of a 1930s steamship that takes visitors for an hour-long scenic cruise along the Miles River.

While in St. Michael’s, we stopped at Justine’s ice cream parlor for something sweet: a chocolate-pistachio marzipan shake for me, and a Bing cherry cone for my friend. From there, it was off to Tilghman Island, to watch fishermen reel in dinner from the docks, and see the drawbridge over Knapp’s Narrows rise up and down to let leisure boats pass through.

It was a wonderful road trip, and easy, too—just hop the ferry to Delaware, amble through rolling farmlands to Maryland, and you’re there. Though we barely scratched the surface of things to see and do on the Eastern Shore, it made for a perfect summer Sunday.