This Bay Was Made For You And Me

10 great weekend excursions on the Chesapeake Bay.

July 8, 2009


Dreams of exotic destinations fuel our passion for the yachting life, but mostly we mess about on waters close to home, balancing passion against the demands of work and family. In the real world, where cruising happens in small bites, the Chesapeake Bay is a weekender’s smorgasbord. Stretching 200 miles from the Susquehanna River to the Atlantic Ocean, the Bay boasts 4,500 square miles of water surface, 20 rivers, hundreds of creeks, 400 marinas, and 40 cities and towns worth a visit. Honky-tonks, hurricane holes, down-home dining, and haute cuisine-the Chesapeake satisfies a yachtsman’s bigger-than-life hunger for variety.

Sail with us first to Baltimore and then south down the Bay as Yachting explores 10 excellent weekend destinations, each with its own peculiar twist and a tip.

1. Baltimore For Love Of “The Game


Nowhere is baseball more in sync with boating than Baltimore, with both their seasons beginning in april and playing out through October. Pilot your vessel to the city’s inner harbor, a once-industrial district that has become the standard for waterfront redevelopment in america. Five inner harbor marinas can accommodate anything from a runabout to a megayacht at the doorstep to the city’s entertainment and dining district.

Even if you’ve resisted going to a game your entire life, Baltimore is the place to relent and repent. Oriole Park at Camden Yards is a magnificent stadium just three blocks, or a 10-minute walk, from the harbor.

Tip: Choose a weekend when the Orioles host Boston and you’ll find yourself amidst a boisterous combination of fans, since New Englanders love to follow the Red Sox to Baltimore, and do so in droves. See also


2. Chestertown For Goofy Fun

Speaking of Boston, when the British closed down that new England port in 1774, the citizens of Chestertown, Maryland, held a “tea Party” of their own in solidarity with their rebel comrades. Townies stormed the Brigantine Geddes and dumped its cargo of British tea into the river-a fact this quaint Eastern Shore community of 5,000 will not let us forget.

Ease of navigation and scenic anchorages make the Chester River a popular destination in its own right, but only during Memorial Day weekend can you observe the region’s goofy inner self. The centerpiece of the tongue-in-cheek Chestertown Tea Party Festival is a tea-dumping reenactment whose participants sport full 18th century drag, with Sultana, a schooner replica, playing the part of Geddes. The festival’s raft race, usually held on Sunday, tests contestants “ability to plumb the depths of imagination and maintain delusional visions of glory.” One year a floating cadillac competed.


Tip: Avoid congestion at the chestertown anchorage by dropping the hook in one of the numerous nearby creeks and take your tender to the party. See also and

3. Annapolis For Ego And Aerobatics

Naptown in springtime is glorious for reasons not limited to perfect weather. Commissioning Week for the U.S. Naval Academy brings the annual performance of the Blue Angels precision flight team thundering over the Severn River. You’ll have to duck out of the office for a couple of days, since this usually happens on a Wednesday afternoon, but there exists no better viewing seat than the “flying” bridge of your own boat, anchored off the academy seawall.


Once the Blue Angels have revved you up, consider parading your boat up “Ego Alley,” a basin for city dockage that deadends, forcing the helmsman to perpetrate a close-quarters U-turn before the assembled multitude of hyper-critical and often inebriated gawkers.

Tip: For a restaurant scene slightly less crowded with proud parents and visiting dignitaries, consider Eastport rather than downtown. (Every Eastport street that deadends on the water has a dinghy dock.) See also

4. Shaw Bay For Music Afloat

Shaw Bay on the Wye River is a protected spot on the Eastern Shore favored for raft parties and fleet rendezvous, but if you arrive on the first Saturday after Labor Day, you will find yourself in the audience of an annual musical event jokingly dubbed “Shawlapalooza.” Expect performances by the popular nautical balladeer Janie Meneely and the chesapeake heritage duo “them Eastport Oyster Boys.” (Motto: good hat, good dog, good boat.) Drop the hook, launch the dink, and gather around the rafted boats with the big sound system for a free show.

Tip: Bring a rod and reel. The waters around the Wye are thick with hungry rockfish-local lingo for striped bass-and the fishing’s good at this time of year.

5. Galesville For Good Music On The Hard

The village of Galesville on the West River of the Western Shore is deceptively sleepy during the week. But on weekends, particularly during the warm months, Galesville will rock the topsiders right off your feet. The venue is Pirate’s Cove, a restaurant, inn, and marina complex with two live music stages-Pirate’s Lounge and Big Mary’s Dock Bar. The marina can accept transient vessels of up to 65 feet LOA. Owner Bob Platt draws his talent from the vibrant music scenes of Washington, D.c., and nearby Annapolis. Be prepared to dance.

Tip: Inquire in advance about the Pirate’s Cove headliners and plan your cruise to coincide with one of their occasional bigname bookings such as howlin’ Eddie Rogers, Chip Davis, or Melanie C & Kurt Nilsen.

6. Easton For Art In “Plein Air”

Easton on the Tred Avon River has just 12,000 residents, but enough Bohemian qualities to suggest that a force of nature had ripped it like a rib out of New York City’s side and plunked it down on Maryland’s Eastern Shore. Easton, you see, is an art capital, excelling in matters visual and culinary.

Enjoy a four-beret experience by timing your arrival to coincide with the Plein Air Easton Competition & Arts Festival in July, which draws reputable artists from throughout the U.S. The French “(en) plein air” literally means “in the open air,” so you will find painters and easels around every corner, many capturing nautical subjects on canvas. Saturday features the “Quick Draw” competition as artists and observers crowd the Victorian downtown for a two-hour painting competition.

Tip: If you are the type that hauls bicycles around on your deck, dock at Oxford or St. Michael’s instead. Established bike routes to Easton are 20 and 16 miles respectively through flat farm country. See also

7. National Harbor For Dining With Lincoln

The National Harbor development on the Maryland side of the Potomac River has been a game-changer for Potomac River cruising. To better justify your 96-mile passage from the Chesapeake, this new minicity has incorporated a modern big-boat marina at the doorstep of Washington in time for what promises to be a fascinating era in U.S. history.

Let us suggest a loop: By cab from the marina to attractions such as the Lincoln Memorial, the first stop for many who visit D.C. go early before the stifling afternoon heat, then retreat into the city’s subway system to reach downtown Alexandria, a hub of fine eateries, for a train-cum-trolley-ride. After lunch, tour the Torpedo Factory arts center, then take the water shuttle back across the Potomac to National Harbor.

Tip: Carry small bills for tipping the many deserving sidewalk musicians of Alexandria, some of whom are quite good. See also

8. Smith Island For Dessert

Enter the harbor at Ewell at the middle of a rising tide (especially if you draw more than 5 feet) and tie up alongside the big wharf. You will step off your boat into a world different from the one you left. The islanders are watermen through and through. Their speech echoes the lilt of Elizabethan English. Ubiquitous orange-blooming pomegranate bushes enliven streets of tidy, shaded homes.

Smith’s pride is its signature product, the Smith Island layer cake, which, after centuries in the baking, was finally named the Official Maryland State Dessert last year. Ten layers high, the official cake is the one with fudgy icing and yellow cake, though the ladies of Smith will do just about any combination of icing and cake flavor you can dream up.

Tip: Don’t come here with an empty cooler. Smith Island is dry. See also

9. Crisfield For Crabs And A Waterman Spectacle

At the restaurants, plain paper is spread on rustic tables. Then come mallets, butter, and Old Bay seasoning. The crabs arrive steaming hot in a bucket. The idea is to smash, pick, dip, and enjoy. It is a feast sublime and worth the effort.

Labor Day weekend transforms “The Crab Capital of Maryland” into a celebration of all things waterman. Everyone knows that of the many maneuvers in boating, docking holds the greatest potential for embarrassment. So, to achieve the greatest possible excitement, Crisfield has turned docking into a timed event, replete with churning water, black smoke, and line heaving-and without penalty for ramming the pilings. For sheer oddity the festival also puts on crab races, crab-picking contests, and a for-real beauty pageant to select Miss Crustacean.

Dockage is available at Somers Cove Marina, a large modern facility.

Tip: When eating crab à la smash and pick, save the bigger critters for last as an incentive not to be lazy or wasteful.

10. Norfolk For A Museum Fix

As you enter the harbor, the muscular gray steel of the Atlantic Fleet will leave no doubt that this is a Navy town. So it is just plain bizarre that the late U.S. Army General Douglas MacArthur is buried and commemorated in the bosom of a service that he considered his rival for glory.

The MacArthur Memorial is just a 10-minute walk from the city’s waterfront, where another museum will prove a bit more entertaining for the kids aboard. Nauticus, an outstanding maritime science center, lives up to its name with a rich assortment of permanent exhibits exploring our relationship with the sea. There is a shark-petting lagoon, an interactive battleship design exhibit, and sub warfare simulator, all designed for children and teens.

Tip: As a quieter alternative to the bustling Waterside Marina, consider docking your boat at Nauticus’s own marina, which accepts vessels 26 to 60 feet LOA. See also and


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