En route to the Eastern Shore. Photo by Craig Ligibel The Pearl of the Chesapeake My first trip to Rock Hall almost ended in disaster. My wife and I were taking our first trip on the Bay via a rented 36-foot twin-screw trawler we had chartered from a company in Baltimore’s Inner Harbor. “Stay in the channel until you pass Red Marker 2. Take a heading of 115 True to the Rock Hall markers. Mind the Swan Point Bar. Follow the markers in. Take right into Harbour Haven Marina. Have a nice trip.” Such was my briefing from the charter company. What could possibly go wrong? I was an experienced boater with more than 10,000 miles under my belt. The boat had two engines and air conditioning. And the weather promised to be warm (and most likely buggy). What the heck? We wanted to stretch our Florida-based sea legs with the eye towards relocating to Annapolis. We followed the charter company’s directions to the letter… until we turned down the wrong alley at Harbour Haven. Got firmly stuck in the muck. And spent the next hour backing and forthing as this single-screw big sailboat driver attempted to master the intricacies of maneuvering a craft with twin screws in very tight quarters all the while trying not to dredge a new channel back to the T-head. Welcome to Rock Hall. That trip was over a decade ago. I have since learned that Chesapeake Bay muck is a pretty forgiving if slippery substance. We have since relocated our modest fleet of 1970s-era craft from the land of sunshine to their new home on Little Aberdeen Creek just off the South River. No more twin screws! Dinghies come ashore at Rock Hall's Pirates and Wenches Fantasy Weekend. Photo by Bernadette Van Pelt And, the town of Rock Hall has come of age with a host of fun things to do to entertain the whole family. The centerpiece of Rock Hall’s summer is the Pirates and Wenches Fantasy Weekend. Now in its ninth year, the festival runs August 12-14. It boasts a full measure of aaarghing for mateys young and old. Last year, the event saw more than 5000 people at some portion of the festivities. Highlights include a decorated dinghy contest, rum tasting, a Caribbean-style beach party, sea shanty sing-along, and enough pirates strolling around to make Captain Jack Sparrow proud. Suzanne Einstein and her charter captain husband Mark are in charge of the event. But a visit to Rock Hall doesn’t have to be all about Pirates. According to Mayor Brian Jones, the town has begun a new program called Festive Fridays on Main. “It’s a street fair that kicks off at 5:30 p.m. each Friday during the summer,” says Jones. “We’ll have music, entertainment, and dining and shopping.” Oysters at Waterman's. Guests are encouraged to slow down, smell the roses, and partake of an ice cream cone or milkshake from one of Main Street’s two ice cream stores, the venerable Durdings and the newly-established Get the Scoop. For visitors with a hankering for a musical interlude, Rock Hall’s Mainstay has something for every musical taste, from rootsy rock to Appalachian folk, all served up in a funky 100-year-old storefront that has played host jazz greats like guitarist Charlie Byrd in its almost 20-year history. Several Rock Hall restaurants and bars also offer music during the weekends. Check out the doings at the Harbor Shack and Waterman’s Crab House for a schedule of upcoming events. Both venues offer a venue with a view, plus plenty of fresh Eastern Shore seafood and grog. For a little more upscale dining, the Inn at Osprey Point offers white-tablecloth service featuring creamy lobster bisque and its signature crab cakes. Wednesdays are burger nights. And for the morning caffeine fix, get your cup of Joe at Java Rock on Sharp Street. Summer in Rock Hall kicks into high gear in early July. That’s when the town hosts a one-of-a-kind Fourth of July weekend, starting with the Rock Hall Baby and Beauty pageant at the Fire House July 1; Waterman’s Day festivities at the waterfront July 3 followed by a fireworks extravaganza starting at 9 pm; and a good old fashioned parade down Main street July 4. Waterman’s Day celebrates the men and women of Rock Hall who make a living fishing local waters. The event showcases boathandling skills with such events as Most Patriotic Work Boat Contest, Anchor Toss Contest, and Work Boat Docking Contest. Be advised: spectators are cautioned to look lively for possible drenchin’s from boat captains “who come in a little hot” when attempting to dock their craft. Don’t forget fishing. Rock Hall boasts one of the most active charter fishing fleets on the Eastern Shore. Rock Hall's Fourth of July Holiday Parade. Photo by Steven G. Atkinson Back in Colonial times, Rock Hall was served by a schooner ferry from Annapolis. George Washington probably slept here during one of his 10 transits to points north. On his last trip, his ferry ran aground en route back to Annapolis. George vowed never to make that particular voyage again! No need to take a ferry to Rock Hall today. Or sample its famous Eastern Shore seafood cuisine with wooden teeth. Approaching Rock Hall Harbor from the water is pretty straightforward. The entrance channel leads north between converging breakwaters to two channels within the harbor. One channel leads to an anchorage basin at the west end of the harbor, then eastward paralleling the waterfront at Rock Hall to a basin at the east end of the harbor. There are a number of marinas in and around the Rock Hall area. They include Rock Hall Landing; Haven Harbour Marina; North Point Marina; and Osprey Point Marina. Have a great time. And don’t mind the muck. It’s easy on boat bottoms, and the memory of one’s encounter with it are easily erased with a tot of rum. Aaargh. by Craig Ligibel