Experience the maritime history, landscape, and sense of community of Maryland's Eastern Shore.

Catch the sunrise over the waterfront at the Inn at Perry Cabin by Belmond.
Deborah Jaffe

Tilghman Island

On August 28, 2011, the day after Hurricane Irene wreaked havoc in the Caribbean and then continued along the East Coast, nearly all the residents of Tilghman (population 784) gathered at the Tilghman Island Country Store. The proprietor, Patricia McGlannan, had strung up a single generator-powered light bulb, to which they were drawn like moths. The islanders had already stocked up on emergency supplies. All they really needed was an opportunity to connect. "Everybody came to catch up on the latest news and check in on their neighbors," McGlannan says. "In Tilghman, gossip is gospel and the hospitality is endless."

The country store—which serves take-out breakfast and lunch to locals and travelers alike—carries handmade duck decoys. McGlannan suspects that many of them are ultimately used only for decoration, but they're fully functional, just like the picturesque boats around Tilghman. Here, seventh-generation watermen rise before dawn to prepare their gear. They're not called fishermen, because their source of income changes with the season—crabs in summer, oysters in winter, and fishing in the months between.

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If you're lucky enough to be there when the Tilghman Island Volunteer Fire Company is hosting its monthly cookout, you can line up alongside the watermen in front of the station to get a plateful of roast chicken and the best baked beans you've ever tasted. Once you've had your fill, visit the Tilghman Watermen's Museum and Crawfords Nautical Books, where you can browse through over 12,000 titles, which cover "all watery categories."

Black Walnut Point is one of many scenic spots on Tilghman Island.
Deborah Jaffe

Standing at the southernmost tip of Tilghman Island, on the scenic Black Walnut Point, you might look out over the water and feel as though you've reached the end of the world. But you're really just at the threshold of another, because in this Eastern Shore community, land and water are equal parts home.

St. Michaels

Bicyclists are pedaling everywhere in St. Michaels, reminding visitors that this town is all about slowing down. There aren't any dedicated bike trails, but Talbot County has mapped-out routes that lead from St. Michaels to Tilghman, as well as the more populous town of Easton. You can rent a bike at Shore Pedal & Paddle to travel along the best-loved, 29.6-mile path known as the Oxford/St. Michaels Trail.

Awful Arthur's in St. Michaels tops oysters with chorizo, jalapeño, and Gouda.
Deborah Jaffe

Almost all of St. Michaels' bicycles include baskets, which are ideal for carting around small treasures found en route. At Antiques on Talbot, you'll find collectable oyster cans as well as oyster plates and crab dishes. It's pretty hard to reach a consensus on which restaurant makes the best crab cakes in town, but two of the most reliable front-runners are Bistro St. Michaels and 208 Talbot, where the Eastern Shore staple is served seasonally and impeccably with fried green tomatoes. Be sure to check out Awful Arthur's for some great oysters and St. Michaels Crab & Steak House for the best of land and sea.

St. Michaels Crab & Steak House works magic with seafood.
Deborah Jaffe
The Inn at Perry Cabin by Belmond is a St. Michaels icon. The original structure, built in 1816, was designed to look like a commodore's cabin, a fitting style for this waterfront property.
Deborah Jaffe

Boutique accommodations—like Five Gables Inn & Spa and Old Brick Inn—are right on Talbot Street, and the alluring Inn at Perry Cabin by Belmond beckons visitors from around the world to its acreage on the edge of town. The original building dates back to 1816 and was designed to resemble a flagship commodore's cabin.

Visit the Chesapeake Bay Maritime Museum in St. Michaels.
Deborah Jaffe

It's fitting, then, that less than a mile away is the Chesapeake Bay Maritime Museum, where you can work as a boatbuilder's apprentice for a day. Capt. Ed Farley docks his skipjack nearby. The H.M. Krentz (along with the Rebecca T. Ruark of Tilghman Island, built circa 1886) is one of the last two privately owned skipjacks that give tours.

On a typical two-hour excursion, you can get a feel for what it's like to work the water as Captain Farley demonstrates his use of traditional tools and shares fascinating stories that illuminate the Chesapeake Bay's fragile ecosystem.

Charter a sail on the Rebecca T. Ruark, built around 1886 and docked on Tilghman
Deborah Jaffe

As for the Rebecca T. Ruark, Capt. Wade Murphy Jr. had long pined for her until he finally managed to buy her in 1984. Revered for her speed, the Rebecca actually sank during a gale in 1999, but the fabled boat was raised with the help of the Maryland Port Administration. Repairs made her suitable to carry lots of eager tourists, whom Murphy regaled with captivating stories of the Chesapeake region. His son, Wade Murphy III, is also a waterman.

A flour refinery located in the Old Mill District has been repurposed to house stores including The Mill Vintage Market and Iron Will Woodworks, a salvage company founded by Tracey Miller and her husband, Mark. Their inventory varies from one day to the next, but you can be sure they'll have something you've never seen before—a scale from the birthplace of President John Quincy Adams' wife or an 1870 corn sheller that has been converted into a bar. "If we don't tend to history, then it just fades away," says Mark. "In St. Michaels, we take pride in preservation."

Oxford, Cambridge, and Beyond

Baked Brie and Duck Fat Burgers make The High Spot a Cambridge favorite.
Deborah Jaffe

Travelers headed south of St. Michaels can reduce their trip time and also up their enjoyment via the Oxford Bellevue Ferry, which is believed to be the country's oldest privately run ferry service. On the Oxford side, treat yourself and linger over a few of the 600 ice-cream flavors in rotation at the Scottish Highland Creamery, and then move on to live entertainment at Cambridge's RAR Brewing. A couple other hot spots in Camrbidge include Bistro Poplar for sweet treats and The High Spot for a delicious lunch. But don't get too settled: Some of the area's main attractions are farther south in the heart of Dorchester County.

enture to downtown Cambridge for a menu of "thoughtful simplicity," seasonal global fare and decadent desserts at Bistro Poplar.
Deborah Jaffe

Blackwater National Wildlife Refuge, with more than 28,000 acres, has four hiking paths, three paddling trails, and several bike routes, offering plenty of avenues for exploration. (Some trails are closed during certain times of year to protect nesting wildlife.)

Explore Blackwater National Wildlife Refuge.
Deborah Jaffe

The refuge is a breathtaking sanctuary for migrating waterfowl. From the paved Wildlife Drive along the Blackwater River, you can see one of the country's largest populations of bald eagles and—in the distance—the Harriet Tubman Underground Railroad Visitor Center, a $22 million project that opened in 2017 in Church Creek.

Visit the Harriet Tubman Underground Railroad Visitor Center.
Deborah Jaffe

Tubman was born into slavery as Araminta "Minty" Ross on a Maryland plantation in 1822. She spent her youth logging and doing hard labor, while her father quietly taught her how to survive off the land. In 1849, Tubman escaped to Pennsylvania with the help of the Underground Railroad, a network of allies and safe houses.

The visitor center is a way station on a 125-mile, self-guided pilgrimage that takes motorists through rural areas of the Harriet Tubman Underground Railroad Byway, highlighting points of interest from her life. Its location was chosen, in part, because this conserved landscape is one that Tubman would recognize if she were alive today. She returned to the area more than a dozen times after her escape, courageously emancipating hundreds of people.

The 5-foot-tall heroine provided for those in her care by foraging for food in the woods, preparing medicine from wild roots, and navigating the route by following the stars. Should any of her charges lose their nerve and talk of turning back, Tubman was known to aim her gun squarely at the undecided and offer them an uncompromising choice: freedom or death.

Seasonal ranger Kevin McNamara points out that the Harriet Tubman Underground Railroad Visitor Center does not display relics. Instead, it delivers carefully rendered stories, songs, and maps intended to guide people beyond the center's state-of-the-art walls and into the marshes, forests, and inlets that were witness to Tubman's prowess as a naturalist. The land on which she was once enslaved ultimately provided—through her keen survivalist knowledge—the tools of freedom. "This area is Harriet Tubman country," McNamara says. "The entire landscape is our artifact."

Historic Easton

This Eastern Shore town, perched on the Tred Avon River, is the kind of place where you'll seriously fret about data storage because you just can't stop taking pictures. In 1682, Quaker settlers arrived here and built a meetinghouse—one of the oldest churches in America—that still welcomes the faithful. Downtown Easton has tree-lined streets dotted with local shops and restaurants, and it's also home to architectural gems such as the Avalon Theatre and the Tidewater Inn (Elvis slept here). The Hill is an African-American neighborhood that's thought to be even older than Treme in New Orleans. Be sure to visit Easton if you're heading to the Eastern Shore.