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Enjoy Chesapeake Charm in Maryland

Someone once told me there are two kinds of people: those who love the mountains and those who seek the sea. I don’t know if it’s true or not, but I grew up in the gently rolling, green expanses of the Pennsylvania Appalachians, and I’ve always felt most centered and happiest on hills. That is, until I took a leisurely week and ambled down a slice of Maryland’s Great Chesapeake Bay Loop. Within days I was imagining a waterside relocation.

Stretching from the town of North East, which sits at the tip of the great estuary, down to Crisfield, on the southeastern shore, the Loop “is a way to encourage travelers to navigate around the Chesapeake Bay, by land and water, for the quintessential and must-do bay experiences,” said Maryland Office of Tourism public relations specialist Matthew Scales. “Each bay town offers travelers a different experience and bay culture.”

Travel planners can choose the itinerary that best suits their group, but I couldn’t imagine a more magical trip than beginning in the bright lights of bustling Baltimore and ending in the sweet, serene town of Cambridge.


With a rich and diverse assortment of activities, Edgar Allen Poe’s old stomping grounds is the perfect place to start your group’s Bay Loop adventure. I kicked things off at one of my favorite museums in the country, the endlessly fun and funky American Visionary Art Museum, stuffed stem to stern with surprising, delightful work from self-taught creatives. It’s hard not to grin when eyeballing sights like the giant Fifi Le Pink Poodle, a staple of the museum’s Kinetic Sculpture Race, held every May for more than two decades.

The iconic Inner Harbor is also always worth a visit, even if you don’t stop by the National Aquarium, with fascinating exhibits like Shark Alley. The institution isn’t far from Miss Shirley’s Cafe, which serves breakfast fare so incredible it made me groan. There are two other Miss Shirley’s in Maryland, including an Annapolis location where I also dined during my trip — yes, it’s that good. I can’t imagine having a preference on the menu, but I heard that when Guy Fieri filmed an episode of his Food Network show “Diners, Drive-Ins and Dives” at the Roland Park restaurant, he raved about the coconut-cream-stuffed toast. I did, too.

The neighborhood I liked most in Baltimore was quirky Hampden, but Fells Point was a close second. More than 160 of its structures, many daubed in brilliant colors, grace the National Historic Register, so walking through Fells Point almost felt like sitting in on a history class, just a lot more rousing. Before departing the city, group travelers who make a study of the past will want to spend some time there, as well as at Fort McHenry National Monument and Historic Shrine. The fort, which stood strong against British bombardment during the War of 1812, was the inspiration behind Francis Scott Key’s poem that would become eventually become the national anthem. As such, it’s profoundly moving ground.


Maryland’s capital, Annapolis is a lively charmer that boasts a brick-paved historic district lined with beautifully kept buildings, plenty of fabulous cuisine and the U.S. Naval Academy’s storied, gorgeous grounds. The city also offers a chance for groups to set sail on the Bay’s windswept waters as well as a host of other activities.

When I arrived in Annapolis, downtown was abuzz with artist tents, food vendors and musicians playing live, part of the First Sunday Arts Festival, which takes place May through September. Other city events include October’s U.S. Sailboat Show, the largest in the world, and Commissioning Week in mid-May, a huge draw for visitors thanks to the U.S. Navy Blue Angels’ airshow, which celebrates the Naval Academy’s graduating class.

Anytime is a good time to visit, according to Chip Seymour, a retired Navy captain who served as guide during my tour of the academy.

“Tours generally end in the chapel at the crypt of John Paul Jones, which is magnificent,” Seymour said. “But people should also be sure to stop by our museum. They have the original ‘Don’t give up the ship’ flag from the Battle of Lake Erie in the War of 1812, and the finest model ship gallery in the world is on the second floor. The wooden models go back to 1650.”

Annapolis is also home to the Woodwind, a gorgeous 74-foot wooden schooner that can be chartered for private sails. Captain Jennifer Kaye will regale your group with tales about when the hit movie “The Wedding Crashers” was filmed aboard her vessel, and she’ll let guests take turns at the wheel of it, too.

Afterward, you might want to do what I did and head to local favorite Boatyard Bar and Grill for the Bay’s best soft-shell-crab sandwiches before taking off for the Chesapeake Bay Environmental Center, across the Bay Bridge on the Eastern Shore. Groups can tour the birds-of-prey exhibit, learn about the fight to restore health to the Chesapeake and wander the walking trails crossing the 510-acre preserve.

St. Michaels

Speaking of “The Wedding Crashers,” the Vince Vaughn-Owen Wilson comedy was shot on the grounds of the magnificent Inn at Perry Cabin in St. Michaels. Treat your group to a meal there — the resort plays host to sublime private events in addition to Hollywood moviemaking — and be sure to give them time to wander the spectacular waterside grounds, as well-heeled and gracious as the rest of the town.

A sparkling little Colonial jewel that sits pretty on the Miles River, St. Michaels is slow-paced and friendly, but neither stuffy nor boring. There are more than enough little shops on its neat streets to keep things interesting, among them Lyon Distilling Company, St. Michaels Winery and Eastern Shore Brewing, all within steps of one another.

Groups can take a tour of Lyon Distilling with its appealing owner, Jaime Windon, a former photographer who is happy to let you sample her product. I also enjoyed rubbing elbows with the locals at Eastern Shore Brewery’s ultra-relaxed taproom. It’s clearly a gathering spot for the community, the kind of laid-back joint where the bartender brings her dogs to work with her.

In a town of treasures, the dearest might be the 18-acre, 12-exhibition-building Chesapeake Bay Maritime Museum. I spent the day there, breaking only for a seafood feast next door at the Crab Claw that was the trip’s best. The museum features exhibits that detail what life is like on the Bay for everyone and everything from oystermen to waterfowl. It also offers a “floating fleet” of historic vessels, specialized tours and the chance for groups to get hands-on in a working shipyard, learning skills like blacksmithing and steam-bending mast hoops.

“We want you to smell the wood, to feel the metal,” Tracey Johns, the museum’s vice president of communications said. “You’ll never find anyone in a costume here — ever — because that’s not authentic. I think when most people come in, they think, ‘Where’s the museum?’ I’ve been here nine years, and every single day I see something new and different.”


About 45 minutes south of St. Michaels, past expansive agricultural fields, is sleepy Cambridge, a historic community not far from where Harriet Tubman came of age before escaping those who enslaved her. The town made national news in May with the debut of the striking downtown mural that depicts the liberator reaching her hand forward, seemingly toward the viewer. Groups should stop for a peek before heading to the Harriet Tubman Underground Railroad Visitor Center in nearby Church Creek.

Opened in early 2017, the center sits within a 17-acre state and national park that abuts the Blackwater National Wildlife Refuge. With marvelously realized exhibits that explore Tubman’s extraordinary life, the space taught me much I’m sad to confess I didn’t know about her, including her service as a spy during the Civil War and her advocacy of equal rights for women.

For an immersive look at the land where Tubman toiled, groups can split up and tour the Wildlife Refuge by bike and kayak with rentals from Blackwater Adventures Chesapeake Bay. Pedaling through the bucolic landscape was a joy, but so was meeting the company’s proprietor, Matt Meredith, who whisked me away on an off-the-cuff visit to the tiny Bucktown General Store, which his family also owns. Nearly unchanged for more than a century, the store is where Tubman was hit in the head with a counter weight as a young girl, almost killing her.

Meredith’s mother provides group tours of the store and the surrounding area, but I recommend asking for a special escort by her ebullient, engaging son. He’s an example of what truly makes the Great Chesapeake Bay Loop worth the trip. It’s not merely the stunning landscapes and waterscapes, the history and the world-class seafood. It’s also the warm, welcoming people who call it home.