Issue: From the Chesapeake Bay Magazine Archives
Destination: Rock Hall, MD

With its 300th birthday just around the corner,Rock Hall, Md., 
has reinvented itself as a busy boating community. [November 2006]

By Michael Brown
Photography by Michael C. Wootton

Our 26-foot sailboat, a venerable Pearson Ariel, can be a bit moody at times, but thankfully this wasn't one of them. On a glorious spring day we fairly zoomed up the Chesapeake from Galesville toward Rock Hall, Md., and as we approached, the town's baby-blue water tower grew easily visible amid the flatness of the Eastern Shore. The three of us—my wife Margaret and I, and the aforementioned Pearson—had been to Rock Hall before, but it had been a while. On earlier visits we had tied up in nearby Swan Creek; this time we were headed for the town harbor itself. Rock Hall celebrates its 300th birthday in 2007, and we were anxious to see what was up in this one-time watermen's village as it neared such a notable mark.

Clearing Swan Point Bar, we headed north between the bar and the shoreline to flashing "4." There we turned to starboard and made for the stone jetties at the entrance to Rock Hall. Sails down, the Atomic Four on, we put-putted into a harbor that immediately struck me as just what a harbor should be: compact and cozy. A quick trip around the perimeter, keeping a series of red daymarks to starboard, brought us to Rock Hall Landing Marina. As we pulled up along dock D, marina co-owner Jim Lancaster took our lines and gave us a quick briefing on how to get "downtown," about a 10-minute walk from the waterfront.

For generations, of course, the waterfront was the downtown, the focus of all activity in Rock Hall. In colonial times, the town was a vital junction in the transportation system between Virginia and points north. Packet ships regularly ferried goods and travelers from Annapolis to Rock Hall. From there it was only a hundred miles or so by road (such as it was) to Philadelphia, capital of the new nation from 1790 to 1800. Not surprisingly, some heavy hitters of the day found themselves passing time here:
        "At Rock Hall, twelve miles from Chestertown, we watched all day for want of a vessel to take us over. . . . We talked, dined, strolled and rowed ourselves in boats, and feasted on delicious crabs." So wrote Thomas Lee Shippen, a gent from Virginia, back in 1790, the "we" referring to two buddies of some note, Thomas Jefferson and James Madison. Records also show that none other than George Washington made the Annapolis to Rock Hall run at least eight times.

Obviously, much in and around this Eastern Shore town has changed since the founding fathers last laid eyes on the place. Some of the change has been difficult and wrenching as the town has shifted, in the last 20 years or so, from a watermen's community to largely a transient one, with an enormous base in recreational boating. Indeed, greater Rock Hall has more boat slips than it has year-round dwellings.

These days, a visitor's repast is just as likely to involve knocking back a latte at Bay Leaf Gourmet as knocking the brains out of some hapless crustacean. But the activities of Mr. Shippen and company while awaiting further transport in 1790 are still very much the highlights of a stop today in this quiet, unassuming, easy-going community. The Philadelphia connection has endured. Not only are there more than a few transplants here from greater Philly, many, many Pennsylvanians (not to mention their neighbors in New Jersey and Delaware) keep their boats here—making it one of the largest bases of what is jokingly called the Pennsylvania Navy. And Rock Hall remains a place for talking, dining, strolling—in short, accomplishing absolutely nothing of any moment and enjoying every second of it.

The heart of Rock Hall is Main Street between Sharp Street and Rock Hall Avenue (Maryland Route 20). By all accounts, this tenth-of-a-mile block was fast becoming a road to aesthetic and economic nowhere, until revitalization efforts in the 1990s reversed the slide. Today it's a pleasant small-town promenade, not too fancy or cute, just pleasant—and real. Come to think of it, that's a pretty good description of Rock Hall in general.

During the summer, visitors can get around town on a green old-fashioned trolley. Gary Stein of Philadelphia was visiting his parents' retirement home in Rock Hall several years ago when he gave a couple of boaters and their grocery bags a lift back to the marina. "A lightbulb went off," he says, and the Rock Hall Trolley Company was born.

Margaret and I were here a bit too early in the season for a trolley ride, but hoofing it around town was no problem. We began our explorations in Oyster Court, a string of small shops connected by a pedestrian way that runs off Main Street. Tom Sabol, a Pennsylvanian who was instrumental in the town's turnaround, developed the court from cottages he found nearby and moved to the town. Jacquin Smolens, a wood carver originally from Pennsylvania now living in nearby Still Pond, has a studio in one of the Oyster Court buildings.

"The chain saw is the primary tool to do the rough work," he said after inviting us inside. Then come power sanders, grinders and hand tools for the finishing touches, he explained as we admired some of his creations (Margaret was especially taken with a handsome boat-shaped bowl). Smolens, an engaging fellow with a sparkle in his eyes and lots of good Rock Hall stories in his head, has carved numerous large pieces for schools, cities and private institutions around the Mid-Atlantic region. One of his most prominent works here in town is at Main and Rock Hall Avenue (which also happens to be the site of the community's one and only bow to modern traffic engineering, a blinking yellow-red traffic light). There, on the corner, is a larger-than-life wooden statue of a waterman that Smolens carved in the 1970s in collaboration with another local carver, the late Clifton Simms, who had also been the town barber. Another of Smolen's huge watermen stands looking out toward the Bay at the Sailing Emporium marina.

Oyster Court is also home to the Tolchester Beach Revisited museum, devoted to the long-gone amusement park that once stood a few miles north of Rock Hall. "I started off collecting postcards," William K. Betts, the museum's creator, curator and promoter, told me. "One thing led to another, and I ended up with a museum. I call it my retirement project." (He's a former banker from Media, Pa.) The amusement park operated on 155 acres along the Bay at Tolchester from 1877 to 1962, at its height drawing thousands of people a summer, many on steamboats from Baltimore. Along with rides and games, there was a hotel for extended stays. "In its heyday, it was probably the most important resort on the Bay," said Betts, who as a small child visited the park with his parents. In 1989—years after the park structures had been leveled—he and his wife bought a weekend cottage at Tolchester and now live there permanently.

Through old photographs and objets d'park, the museum provides a nicely-focused glimpse into this bit of Eastern Shore history. I especially liked the sign: Entrance 25¢. Pay as you leave—a remnant of a more trusting era.  

For another taste of the past—this one literally a taste—we stopped on Main Street at Durding's Store, Rock Hall's first pharmacy. Built in 1872, it was a community meeting spot for generations. In 1987 Art Willis and his wife Mary Sue (who also own the Sailing Emporium) bought the defunct building and restored the interior to its 1930s appearance. Reopened in 1993, the store retains the original marble fountain, bar stools, old wooden booths and cabinetry. It also has a menu that features real malted milk shakes, ice-cream sodas and other fare served a half-century ago in a corner drugstore.

Store manager Patricia Kelley told us of an elderly couple who came in intent on sitting in a particular booth. It was occupied, but they didn't mind waiting; it was their 75th wedding anniversary and they'd gotten engaged in that very booth.

The headline over a 1952Baltimore Sunarticle displayed in the Rock Hall Museum on Main Street declares Rock Hall as "The Bay's Rockfish Capital." If location is what drew colonial forefathers here in the 1700s, it's also what gave the town its economic engine for decades. Located directly on the Bay but with close, easy shipping links to seafood-hungry towns like Baltimore and Philadelphia, Rock Hall was perfectly situated to thrive when Bay oysters, finfish, clams and crabs were the hot commodities.

Ron Fithian, a waterman for 27 years and now Rock Hall's town manager, told me it used to be that 75 percent of the people in Rock Hall had something to do with the seafood business. If the man of the house wasn't a waterman, he most likely worked in a packing house, a
boat repair shop or some other seafood-related endeavor.

Fithian went out on the water as soon as he graduated from high school in 1969; that's just what you did. Back then during winter oystering, 132 boats would show up each day like clockwork at Swan Point and catch the limit—25 bushels per rig, he recalled. No longer. The local seafood industry here was already on the way downhill when Hurricane Agnes hit in 1972, and she put the descent into high gear. Last year only three Rock Hall boats were oystering, Fithian said. Commercial rockfishing and clamming are also down to a trickle, "Crabbing is the one industry hanging in there," he told me.

But as Rock Hall was losing one industry in the 1970s, it was gaining a new one: recreational boating. "It's the location. Location is everything," says Art Willis, who in 1978 opened the Sailing Emporium, one of three commercial marinas at the harbor. Rock Hall is right smack on the Bay, so there's no long river to negotiate to reach open water, a feature especially attractive to sailors. And for the multitudes of boaters home-ported in Annapolis and Baltimore across the Bay, Rock Hall is an easy reach.

As George Washington undoubtedly appreciated, the town is also an easy reach by road from Philadelphia and other points north. From Rock Hall, you can see the Bay Bridge clogged on summer weekends with traffic escaping Washington and Baltimore. People from Philly and environs don't have a bridge hassle; they can drive straight down the Eastern Shore. The Rock Hall population (1,700 to 1,800 by Fithian's estimate) swells during the summer, and the bulk of the influx comes from Pennsylvania, New Jersey and Delaware. Willis says his marina even has slipholders who live in Manhattan. Today greater Rock Hall, including nearby Swan Creek, has nine marinas with a total of almost 1,200 slips. The community also offers a dozen or so B&Bs and small inns, two motels and at least 14 eateries, offering everything from carry-out subs to fine dining. The economic and social changes in Rock Hall have produced some low-rise condos on the waterfront, as well as some new homes sprouting in the woods between the waterfront and business district.

The town's economic metamorphosis hasn't been painless. As the seafood business disappeared, some residents didn't like what was taking its place, maybe even saw a cause and effect between the two. As Fithian delicately puts it, "There was a period of time when there was a division of opinion." But that period seems to be mostly over. Though Fithian acknowledges a certain sadness as more houses once occupied by watermen and their families become retreats for weekenders and retirees, there's also recognition that the marina jobs and other economic activity that accompanied pleasure boaters and weekend visitors have helped keep the town afloat. "We were lucky. When we lost our Chrysler, our General Motors, which was the seafood industry, we had the recreational boating industry come in and pick us up," Fithian says.

Although down in numbers, Rock Hall's watermen have by no means disappeared—or been forgotten. Several years ago the county bought what was then Pelorus Yachting Center at least in part to give watermen a place to rent slip space at affordable rates. Now called Bayside Landing Park, the marina still has slips for watermen, as well as a public bulkhead where boats can tie up for free during the day to unload their catch. Recreational boaters can also use the bulkhead, which is appropriately adorned with a statue of an oysterman—by sculptor Kenneth Herlihy—and a dedication to "watermen and other working people of the Chesapeake Bay area."

The 2002 edition ofFrommer's travel guide to Maryland and Delaware takes note of Rock Hall's growing number of shops, restaurants and overnight accommodations, and says the town "looks like it will be the next St. Michaels." Personally, I don't think so—at least not anytime soon. The people Margaret and I met, both natives and otherwise, seemed satisfied with the way this community has managed to maintain the quiet, unassuming ambience of the past while building an infrastructure that is unobtrusive but competent at meeting the needs of visitors.

As we were preparing to leave the marina on Sunday, D.A. Hanson, a Reading, Pa., car salesman with a 41-foot Silverton, came over to help us with the lines. "There're no high-rises. There're no horns blowing. [Just] peace and serenity," he said, explaining why each weekend he and his wife drive nearly three hours to their Rock Hall harbor slip. "Have you heard a horn blow?"

Indeed, I had not. Were he around today, the good Mr. Shippen might say, "We talked, dined, strolled, sailed and had a couple of lattes." Three hundred years may have gone by, but Rock Hall still seems to have managed to remain genuine, embracing change while staying faithful to its past.

Cruiser's Digest: Rock Hall, Md.

When we visited Rock Hall this past spring, shoaling accelerated by Hurricane Isabel in 2003 had narrowed the approach channel to the harbor entrance. But in early summer Kent County got state funding to dredge the Bay side of the jetties down to 7.5 feet at mean low water. So getting in and out of Rock Hall shouldn't be a problem, except for the deepest of deep-draft boaters. The harbor itself has good depth—7 to 8.5 feet, according to charts—as long as you don't stray. Some spots outside the marked channels looked like seagull-wading territory. "The deepest boat we've ever had in here was eight and a half feet. They came in an hour before high tide and left at the same time," says Jim Lancaster of Rock Hall Landing Marina.

To reach the harbor, you first need to get to flashing "4" in the north-south channel east of Swan Point Bar. Some local sailors with shallow-draft boats know how to cross the bar. But the prescribed route—and the safe one—is to round green can "3" south of Rock Hall and head north. From flashing "4," you should be able to see the harbor entrance. If visibility is poor, advises Art Willis, owner of Sailing Emporium, head 060 degrees magnetic to reach the jetties, which are marked on the Bay-side by flashing "4" and "5".

The harbor itself is well marked. Once inside the breakwater, you have two choices. For newcomers, the easiest way is to bear left and go clockwise around the perimeter, staying close to shore and keeping the red beacons to starboard. There's also a cross-harbor channel, which is the most expeditious route to the far side. It's marked by "2E" and "4E" and meets the perimeter channel in front of Rock Hall Landing. Head for the fairway between the marina's C and D docks and you will be fine, says Lancaster.

Remember one important point: The far eastern side of the harbor is not dredged, making it impossible to go all the way around. When you're ready to leave, you have to backtrack along one of the two routes you took coming in.

The harbor, which is too tight for anchoring, has three commercial marinas, and all take transients.
(1) North Point Marina (410-639-2907) with 135 slips is just inside the breakwater and to the left.
(2) Rock Hall Landing Marina (410-639-2224), the closest to the town's center, is between North Point and Sailing Emporium, which both sell fuel. During daylight hours, boaters can tie up free of charge at the county-owned bulkhead at the top of the harbor.
(3) Sailing Emporium (410-778-1342) with 165 slips is at the harbor's east end.
For skippers who want a more bucolic setting, there are five marinas north of the harbor along Swan Creek (a popular anchorage) and the Gratitude peninsula, a lovely residential area between the Bay and creek. Four of them take transients: (4) Gratitude Marina (410-639-7011); (5) Haven Harbour Marina (410-778-6697); (6) Inn at Osprey Point (410-639-2663); (7) Swan Creek Marina (410-639-7813).

Most of the marinas have bicycles that guests can use to get around. Boaters who want to buy groceries can call (8) Bayside Foods (410-639-2552). Owner Jeff Carroll provides free rides to and from his store, located at the corner of Main Street and Rock Hall Avenue.
The Rock Hall Trolley Company (410-639-7996, toll free 866-RHTROLY) stops at all marinas in the Rock Hall area as well B&Bs, restaurants and other spots of interest—a total of 34 stops each hour. The cost is $4, good for the day.

(9) Harbor Shack Waterfront Bar and Grill (410-639-9996), which opened this summer and (10) Waterman's Crab House (410-639-2261), are on the harbor with waterside dinning and free docking for boaters while they eat.

Eateries in the town center include (11) Bay Leaf Gourmet (410-639-2700), (12) Bay Wolf Restaurant (410-639-2000) (13) Durding's Store (410-778-7957) and (14) Pasta Plus (410-639-7916). In the Gratitude area, there is the (6) Inn at Osprey Point (410-639-2194) and (15) Pruitt's Swan Point Inn (410-639-7454).

For a list of all Rock Hall restaurants as well as B&Bs and other lodging—with maps pinpointing the locations—go to

Things To Do  
Rock Hall and environs offer plenty of opportunities for biking, kayaking, listening to live music and shopping. Here are a few diversions. 

Museums (16) Rock Hall Museum (410-639-2296; www.rock focuses largely on the town's history as a fishing and boating center and includes models of a skipjack, log canoe and other traditional watercraft, about 20 in all. It's in the Muni- cipal Building, a former school on Main Street three-tenths of a mile south of the town center. It has the same hours as the Tolchester museum. 

(17) Tolchester Beach Revisited a museum (410-778-5347; chester) is open 11 a.m.–3 p.m. Saturdays and Sundays (except in January and February) and by appointment. There's no admission fee, but contributions are welcomed. 

(18) Waterman's Museum (410-778-6697; features the tools of the waterman's trade, including lines of all sizes, wooden blocks, eel pots and a clam fork. The collection is in a cottage on the grounds of Haven Harbour Marina. The door is kept locked, but you can get the key at the marina's Ditty Bag store anytime 10 a.m.–5 p.m. daily. 

Art Galleries You can browse and buy the work of area artists at two Main Street shops. (19) The Artists of Rock Hall Gallery (www.rockhall artists) exhibits the work of 26 artists and crafts people, most of them Rock Hall residents. Across the street, (20) Rock Hall Gallery ( is a co-op of 12 people skilled in furniture making, textiles, jewelry, pottery as well as painting and photography. 

Biking (21) Swan Haven B&B (410-639-2527) located on Rock Hall Avenue a little less than a mile west of downtown, rents bikes to the public. The country roads around Rock Hall and in the (22) Eastern Neck National Wildlife Refuge 6 miles south of town offer good biking possibilities. (23) St. Paul's Episcopal Church ( about 5 miles north of Rock Hall at Sandy Bottom and Ricauds Branch roads is on the National Register of Historic Places and makes a worthwhile destination. 

Small Boating (24) Chester River Kayak Adventures (410-639-2001; rents kayaks and leads full- and half-day guided kayak tours, mainly in tributaries of the Chester River. There are also sunset tours in Swan Creek and Tavern Creek. 

(21) Swan Haven B&B also rents kayaks as well as other small boats. The county's (25) Bayside Landing Park has a dual boat ramp for public use, though a county permit is required. If you're interested in a fishing charter, has a list of boats operating out of the area. For sailboat racers, there is organized competition (410-810-0005) outside the harbor two Friday evenings a month, May–August. The town's tiny beach on Beach Road is a good place for sunset watching as well as swimming. 

Music (26) Mainstay (410-639-9133; www.rock presents national, regional and local artists with an emphasis on jazz and blues. Check out the upcoming schedule at their website.