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July 2024 · 7 minute read

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I could tell you about the sunsets and skipjacks and uncomplicated charms, and I will, but a better reason to like Tilghman Island, Md., has to do with the young guy who mooned us from the top of the old Knapps Narrows drawbridge on our first visit. God knows the Eastern Shore tourism people, much less the sheriff, wouldn't approve, but it made me feel, well, welcome.

The day's crabbing done, the tanned and shirtless twentysomething and his two companions apparently had spent too much of a summer Saturday afternoon with brother Budweiser. The mooning done, he ran and jumped a good 30 feet into the Narrows. Then he climbed back ashore, walked stiffly back to his friends' table at the bar/restaurant next to the bridge and sat quietly. Such a stupid stunt easily could have ended in disaster, but it didn't – and it said something about Tilghman that the brochures, especially the glossy ones for new luxury homes, don't mention.

More than any town I've seen along the Chesapeake, Tilghman Island remains unpredictable and independent-minded – independence being the quality every waterman mentions first when you ask about job benefits. Tilghman, a waterman's town very much in transition, retains its essential quirkiness in the face of the powerful forces, natural and otherwise, that are slowly transforming so much of the Eastern Shore.

Out here along the Chesapeake, unpredictable is what you want to be, have to be, because the bay is the ultimate in unpredictable. It is flat, calm and balmy one October moment, covered in fog, a stinging wind and four-foot swells 20 minutes later. It yielded a bounty of oysters for generations of families, but now those who start plying the creeks and flats every October have no choice but to work harder and worry about those truckloads of Oregon oysters arriving sooner at the wholesaler's. Maybe being fond of the quirky and unpredictable is just my reaction to the alarming number of people in this world who are, at this moment, wearing little McDonald's hats and greeting customers in the monotones of many languages. In any case, there is no McDonald's on Tilghman Island. Yet.

What you'll encounter here, if you drive the extra dozen miles past the better known and more often repainted St. Michaels, is one of the state's busiest drawbridges (over the Narrows, the aptly named boater's shortcut from Annapolis and Kent Island down to the Choptank River and Oxford). Beyond that are a couple of family-owned country stores, a bait and tackle shop, some lovingly tended book and collectibles shops, some decoy carvers and wooden-boat builders, a half-dozen inns and B&Bs, ranging from simple to spectacular, and the Harrison family's famous sport fishing-seafood-sleepover empire. You'll also find, rocking in the gentle swells at Dogwood Harbor, one of the country's last commercial sailing fleets – a few proud, aging skipjacks whose captains not only dredge the bay for oysters in fall and winter but, more often nowadays, take tourists on day trips.

On one visit to Tilghman, my wife, Charmaine, and I took one of Ed Farley's half-day sails aboard his skipjack H.M. Krentz. The bay's wild beauty seemed somehow more real when met from the rail of a heaving old wooden sailing boat. Farley's demonstration of oyster-dredging was both intriguing and heart wrenching. He culled by rote a few puny keepers from the dredge's mud, talking quietly about seeding projects and the disease that has decimated the bay's oyster population.

On our most recent day trip to Tilghman, we spent a couple of memorable late-afternoon hours on the Choptank with Randolph Murphy, 42-year-old son of Capt. Dan and Miss Edwina Murphy, as they are known, elders of the oldest clans of watermen here. In his hand-built, diesel-powered workboat, Randy Murphy makes his living on the water pretty much year round – fishing and crabbing when it's warm, oystering and guiding hunting parties when it's not. He has an easy laugh, a permanent wind- and sun-resistant reddish-brown glow, and that Eastern Shore knack for saying more by saying less.

"Oh, it's definitely not for the security," he says of why he remains a waterman. "Yep, making $2,000 one week and $200 the next is not what you'd call security." He leaves you to see that it has to do with being out here between the endless sky and the brownish-blue waters, applying skill and spirit to the waterman's tasks, as his forefathers did before him.

As he's setting out his 4,700-foot crabbing trotline, a 40-foot pleasure sailboat running on diesel crosses it. He gently but precisely slackens the line. Murphy smiles. "You know, we have a saying about sailboaters. The sailboater arrives on Friday with a crisp white shirt and a crisp dollar bill. And he leaves on Sunday without having changed either one of `em."

Our friends Jerry and Maura bought a small place in Tilghman almost a decade ago and now hardly ever spend time around their native Washington. They first introduced us to the island. Most afternoons, they take their 22-foot Seahawk onto the bay just to be out there when the sun sets, and every time Maura talks about her adopted town, she paints from a similarly warm palette.

"The people on the island are always friendly," she says, "but they are also very spontaneous and straightforward. They all have a wonderful way of saying something incisive, of putting their finger right on the point and saying something just . . . as it is."

The Maritime Museum in St. Michaels gives you an excellent idea of how things were on the Eastern Shore. The way things are, on the other hand, changes daily. But you can count on some things, particularly meeting independent and often surprising people with an uncanny ability to sense a school of fish or a storm ahead.

Travel TipsGETTING THERE: Tilghman Island is about two hours from the Beltway. At Exit 7, take U.S. 50 east across the Bay Bridge. Before Easton, turn right on Route 322 and right again on Route 33 east, which ends in Tilghman.

BEING THERE: If you're after sport fishing, start at Harrison's, where the fleet (at last count 14 boats and rising) and fish-finders are hard to beat (410/886-2121). For a more sea-level look at the bay's coves, creeks and wildlife, call Chesapeake Bay Kayaks (410/886-2083). Or take a walk down Mission Road (third left from the drawbridge) to the Choptank. Along the way you'll likely find Dan Vaughan (410/886-2083) among the aromatic cedar shavings of his decoy workshop and Maynard Lowery just up the street building his trademark squat and graceful wooden boats. Two-hour-to-all-day sails can be had on the skipjacks H.M. Krentz (410/745-6080) and Wade Murphy's Rebecca T. Ruark (410/886-2176), the bugeye Mamie M. Mister (410/886-2703) and the restored 1931 pleasure yacht Lady Patty (800/690-5080).

WHERE TO STAY: At the warm and central Sinclair House (888/886-2147 or 410/886-2147), a room and breakfast is $65-$85 a night. At the island's far tip, it's $150 for the 4-person Cove Cottage on the 57-acre wildlife-refuge grounds of the Black Walnut Point Inn (410/886-2452). And there are ever more options in between: the elegant Victorian Chesapeake Wood Duck Inn (800/956-2070 or 410/886-2070), where rates (starting at $135) include a gourmet breakfast; the four-room Lazyjack Inn B&B (800/690-5080), also known for its breakfasts ($130-$195); the quiet and homey harborside efficiencies at Norma's Guest House ($65-$85; 410/886-2395); a two-night weekend package for two, including Saturday dinner and Sunday brunch, for $320 at the Tilghman Island Inn (800/866-2141 or 410/886-2141); or the $175 room/meals/fishing package at Harrison's Chesapeake House (room only: $95-$105; 410/886-2121).

WHERE TO EAT: Choices in Tilghman itself include the traditional seafood specialties of Harrison's plus the prettier (especially at sunset) Tilghman Island Inn, and the outdoor patio on the Narrows or upstairs observation deck of the casual and friendly Osprey (410/886-2330). Directly opposite the Narrows from the Osprey is the newer Pescado's (410/886-2126), where fresh local seafood is married to a modern Mexican-Southwestern menu. For more nearby options, see St. Michaels, Md..

FOR MORE INFORMATION: Call 410/822-4606 for the Talbot County Office of Tourism, or look up the Web site at www.talbotchamber.org.

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