Back in the day, Rock Hall had its fair share of distinguished visitors. George Washington came through town regularly to catch the ferryto Annapolis. Thomas Jefferson stayed awhile with his buddy James Madison to “feast on delicious crabs,” as one 1790 diary records it. On a recent visit, I thought I’d do the same—and soak up some of the atmosphere that has made the village of Rock Hall a laid-back watermen’s paradise for 300 years.

Actually, these days Rock Hall is as much an affluent Chesapeake resort/retirement community as a fishing village, with several new housing developments encroaching on the outskirts of town. Where crab and oyster boats used to clog the harbors (that is, before the railroad throttled the town’s heyday), now pleasure boats serve as the area’s economic engine: Seven marinas and about one slip for every 2,000 residents have earned Rock Hall the unofficial title of “pleasure boating capital of the upper Eastern Shore.”  There are enough transplants—many of whom have roots in cities like Philadelphia and Wilmington—to support one espresso bar, but Rock Hall’s town center remains as easygoing as ever. “There’s development, but it’s not a real fast kind of development,” says Mark Einstein, who runs Blue Crab Chesapeake Tours. “Rock Hall’s laid-back charm is very much intact.”

Here are ten spots where I found that Rock Hall charm.

1 Durding’s Store

This is the kind of place that isn’t supposed to exist anymore: a corner soda fountain with a marble counter and straws in glass cylinders, where kids (and the rest of us) slurp malts, shakes, sundaes, sodas, floats, and—in deference to contemporary appetites—smoothies. Durding’s retains many trappings of the post office, drugstore, and doctor’s office that formerly occupied the circa-1872 building, including a tin ceiling, antique pharmacist’s chest, and classic wooden phone booth. “A lot of people come in and pretend they’re Superman,” says manager Patty Kelly, who whips up concoctions like Miss Patty’s Favorite—homemade apple pie and butter pecan ice cream, topped with caramel sauce. Main and Sharp streets. 410-778-7957.

2 Eastern Neck National Wildlife Refuge

A wooden bridge six miles south of Rock Hall leads to a 2,285-acre refuge for transient waterfowl and avian winter residents. While Canada geese, canvasback ducks, and tundra swans form the bulk of refuge denizens, great blue heron, osprey, and bald eagles can be spotted throughout the year from short, flat trails—a quarter- to one-mile roundtrip—some equipped with viewing scopes. Viewers on a deck alongside the Bayview-Butterfly Trail, for example, behold shorebirds in the foreground, Kent Island waterfront homes in mid-range, and, out yonder, traffic crawling across the Bay Bridge. The
visitor center near the south end of the island occupies a building that, ironically, served as a hunting lodge before the Feds established the preserve in 1962. Stop by to pick up a pair of loaner binoculars and a Waterfowl Census Weekly Data Sheet enumerating recent sightings. 410-639-7056 or fws.gov/northeast/easternneck.

3 Rock Hall Trolley

On weekends from May through July, a vintage green trolley makes a one-hour, three-mile, thirty-four-stop loop hitting just about everything in town: the downtown shopping district, all seven marinas, B&Bs, restaurants, museums, even the public beach and boardwalk at the peninsula’s western tip. You can also hop the trolley for the twelve-mile run to Chestertown. Trolleys operate Saturdays from 9 a.m.-10 p.m. and Sundays from 9 a.m.-6 p.m. All-day fares: adults, $3; children, $1. 866-748-7659 or rockhalltrolleys.com.

4 Smilin’ Jake’s Casual Apparel

Passing through Smilin’ Jake’s purple portals will make you feel you’ve died and gone to Hawaii. The tiny shop brims with Hawaiian ware—shirts, of course, but also mugs, muumuus, and hats with Hawaiian-shirt motifs. “I’ve been a Hawaiian shirt fan shirt since high school,” says owner Jack Heffner, who opened the shop eight years ago because “the town needed it, and it was something I always wanted to do.” Along with a full line of Maui Jim made-in-Hawaii sunglasses, Smilin’ Jake’s is one of only a few retailers that carries Jimmy Buffett’s Margaritaville Shoes and Rock Hall hook bracelets—with tiny crab pot buoys impaled on a fishhook, among other local totems—designed by Rock Hall native Robin Wood Kurowski. 5774 Main St. 410-639-7280.

5 The Mainstay

Ten years ago, a downtown storefront was converted into a nonprofit venue for live music, regular exhibits by local artists, garden club meetings, and “Live Poets Society” readings. The Mainstay’s modestly priced concerts (usually $15) feature jazz, blues, country, or acoustic gigs by local, regional, and national performers—the late Charlie Byrd and Deanna Bogart, to drop a couple of the bigger names. Mainstay décor—mismatched indoor and outdoor furniture—is as heterogeneous as the music. “It’s like sitting in your Aunt Millie’s living room,” says Tom McHugh, founder and director of the popular spot, quoting a bass player from Annapolis. 5753 Main St. 410-639-9133 or mainstayrockhall.com.

6 The Waterman’s Museum

This small bayside museum offers a reasonably comprehensive look at the traditional pillar of Rock Hall’s economy. In one room, a sneak boat used for duck hunting with punt guns is surrounded by the tools of the various Bay trades—not only fishing, crabbing, and oystering but also eeling, catfishing, and turtling. Another room re-creates the interior of a typical “ark,” the floating campers in which watermen lived as they followed the fish. Plenty of fossils and traps and stuffed specimens of local fauna are on display, and the museum even salutes one
particularly unsung breed of workers: oyster shuckers. The museum was founded in 1990 by the parent company of nearby Haven Harbour Marina, but the exhibits come directly from the community. “Once the locals realized we weren’t trying to make a buck, stuff started coming out of attics and basements as free donations,” says Jonathan Jones, Haven Harbour general manager. Free admission; open daily 10 a.m.–5 p.m.; obtain key from Ditty Bag marina shop, about 100 yards west. 20880 Rock Hall Ave. 410-778-6697 or havenharbour.com/hhwatmus.htm.

7 Blue Crab Chesapeake Charters

The Crab Imperial, a Watkins 36 sloop, departs from the dock across from Waterman’s Crab House up to five times daily for ninety-minute cruises into the open Bay or, breeze permitting, north into Swan Creek or south to Eastern Neck Island. The sloop accommodates up to six people, with plenty of deck space to spread out, catch rays, drink in the sunset, stop for a swim, and bond with fellow passengers. “You have three couples who have never met each other and they come back friends,” says skipper Mark Einstein, a native Baltimorean who migrated to Rock Hall in 1998. “I’ve taken people out on their first dates and had them married right on the boat—but not the same day.” $30 per person; reservations recommended. 410-708-1803 or http://www.bluecrabcharters.com.

8 Chester River Kayak Adventures

For even closer encounters with Rock Hall waters, Chester River Kayak Adventures has something for everyone—even the inexperienced and not particularly fit. (Motto: “CRKA is more an eco-tour than an athletic event…Our goal is to keep you in the boat and out of the water.”) Novice paddlers are welcome on any of five three-hour, half-day trips, all of which include landings at secluded beaches and may offer tidal-water views of everything from osprey nests, salt marshes, and beds of sub-aquatic vegetation to waterfront farms and McMansions. Full-day trips (no novices, please) circumnavigate Eastern Neck Island or ply the sometimes-tricky currents of the Chester River. Sunset and moonlight paddles, lessons, and kayak rentals are also available. Half-day trips: adults, $50; children 10 and older, $40. Full-day trips: adults, $90; children, $75 (lunch included). 410-639-2001 or crkayakadventures.com.

9 St. Paul’s Episcopal Church, Kent

Founded in 1692, St. Paul’s was one of the thirty Anglican churches established in (Catholic) Maryland during the reign of Britain’s (Protestant) William and Mary. Completed in 1713 on a back road north of Rock Hall, the current building is notable for its uniform Flemish bond brickwork and a rare semi-circular apse. Peek inside at the red-velvet pews and a tablet commemorating the founders. Most plots in the vast boxwood-shaded churchyard date from the nineteenth century, but a few closest to the building go back even farther. St. Paul’s graveyard even boasts one twentieth-century celebrity grave: the outrageous outspoken actress/
celebrity Tallulah Bankhead (1902-1968), who wound up out here, dah-ling, because her sister, Eugenia, owned a home nearby. 7579 Sandy Bottom Rd. 410-778-1540 or stpaulkent.org.

10 Oyster Court

Oyster Court is an ad hoc metal sculpture garden and a few picnic tables out back of the Main Street stores, surrounded by a half-dozen or so semi-dilapidated shanties housing artist and craftsman studios, shops, and the town visitors center. Sweet Annie’s features “home grown and handmade” decorative soaps, scented candles, beaded jewelry, and such. In one tidy blue shack, Tolchester Beach Revisited commemorates a bygone local amusement park, which, in its day (1877-1962), amused as many as 20,000 visitors a weekend—most
of them arriving via steamers and ferries out of Baltimore—with everything from a carousel and dodge ‘em cars to a bowling alley and harness racing track. Walkway alongside The Mainstay.

When he’s not partaking of Rock Hall’s charms, Theodore Fischer writes from Silver Spring, Md.

Lodging

Inn at Osprey Point. Seven large rooms, in a colonial-looking but modern B&B in a secluded marina-side setting. 20786 Rock Hall Ave. 410-639-2194 or http://www.ospreypoint.com.

Moonlight Bay Inn. Ten Victorian/Queen Anne-style rooms in main lodge and west wing—many with Bay views—steps from a fifty-slip marina. Full breakfast and afternoon tea. 6002 Lawton Ave. 410-639-2660 or http://www.moonlightbayinn.com.

Old Gratitude House. Modernized (DVD players, Wi-Fi) Victorian home on the west end of town with five guest rooms—plus resident Westie—facing the Bay. 5944 Lawton Ave. 410-639-7448 or http://www.oldgratitudehouse.com.

Swan Haven Bed & Breakfast.  Expanded Victorian mansion built in 1898—for $350—with ten guestrooms plus plenty of decks and new glass-walled great room overlooking Swan Creek. 20950 Rock Hall Ave. 410-639-2527 or http://www.swanhaven.com.

Tallulah’s on Main. Four Bankhead-themed suites with kitchens in central Rock Hall. 5750 Main St. 410-639-2596 or http://www.tallulahsonmain.com.

Food

Inn at Osprey Point. Traditional American fare in elegant candle-lit rooms styled after a Williamsburg inn. 20786 Rock Hall Ave. 410-639-2194 or http://www.ospreypoint.com.

Harbor Shack. Pier-side neighborhood hangout features local seafood and steaks, Mexican dishes, live music, DJs, and karaoke. 20895 Bayside Ave. 410-639-9996 or http://www.harborshack.net.

Waterman’s Crab House. Quintessential Maryland dockside crab-cracking joint with all-you-can-eat specials and an outsidedeck with harbor and Bay views. Sharp Street Wharf. 410-639-2261 or http://www.watermanscrabhouse.com.

Bay Wolf. Cozy heart-of-town spot that compatibly mingles Chesapeake seafood with Austrian dishes. 21270 Rock Hall Ave. 410-639-2000.

Java Rock. Bright new cafe with full line of coffee specialties, bagels and pastries, and daily selection of panini (go for the artichoke and Swiss). 21309 Sharp St. 410-639-9909.

Bay Leaf Gourmet. Cheerful break-fast and lunch spot starring a variety of homemade quiches served with an ample Caesar salad. 5757 Main St.410-639-2700.