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The multi-faceted Chesapeake Bay is without doubt one of the world’s premier cruising grounds. For the energetic folks who want to “go and do,” you will find an abundance of historical sights dating back to the 17th century, festivals nearly every weekend, museums galore and crabs prepared every which way. For laid-back types who prefer to just “be,” spacious anchorages and wildlife refuges line the shores. From the mouth of the Susquehanna to Tidewater Virginia, there are ever-changing tides to explore all season.
Havre de Grace, MD, the “Decoy Capital of the World,” is a spirited modern town shadowed in the charms of the past. Multiple historic museums include a decoy museum spotlighting the art of decoy making and waterfowling traditions.
A new Lafayette Trail App outlines a 3-mile loop and 37 stops as part of the Lafayette 200, a bicentennial celebration of the 24 states Lafayette visited during his 1824–1825 Farewell Tour. As Lafayette traveled down the bay from Port Deposit in the 19th century, crowds lined the shoreline cheering the hero’s rockstar status. He made an unscheduled stop in Havre de Grace. Now, two centuries later, “Lafayette” will once again step ashore at recently opened Graw Alley Art Park on July 29. Named after the former horseracing track that operated in the city a century ago, the space has been transformed from an underused alley into a park with landscaped pathways, artistic sculptures, outdoor seating and a series of vivid murals providing a visual tour through history.
The other northern entrance to the Chesapeake from the Delaware River is through the C&D Canal in Chesapeake City, the only Maryland town situated on a canal. Located in the original pump house, The C&D Canal Museum outlines its rocky beginnings in the early 1800s into one of the world’s busiest commercial canals today. Head to the Inn at the Canal for cozy lodging and check out The Rum Garden outdoor drinking area overlooking the C&D. Specialty drinks feature a unique assortment of rums from around the world.
Head south from Chesapeake City to Chestertown, MD, established as a port in 1706, which retains much of its historic charm and well-preserved 18th-century architecture. According to local legend, after forbidding the importing or consuming of tea in 1773, angry residents marched down High Street to the brigantine Geddes and tossed her cargo of tea overboard. The annual reenactment is the centerpiece of the Chestertown Tea Party Festival, May 23 to 25.
Now one of the largest tall ship and wooden boat festivals in North America, Sultana Downrigging Weekend hosts schooners, ships and beautiful wooden boats to explore or enjoy for a scheduled sail. Musical performances and dynamite local food round out the weekend of October 31 to November 2.
On the western shore, a thousand acres by the mouth of the Middle and Back rivers was once a chain of three islands suffering from severe erosion. Dredge material from Baltimore Harbor channels created what is today Hart-Miller Island, a nature lover’s paradise of boat-accessible beaches and numerous vantage points for birding and wildlife viewing, open May to September.
Southbound cruisers will pass several screw-pile lighthouses, a favored construction due to the estuarial soft bottom of the Chesapeake. Maryland’s oldest, built in 1856, was initially installed on a shallow shoal at the mouth of the Patapsco River. Now decommissioned, Seven Foot Knoll has been moved to the Inner Harbor neighboring the historic USS Constellation.
In Annapolis, the photo-worthy Thomas Point Shoal Light is the only screw-pile lighthouse still standing at its original site. Several charter companies including Watermark in Annapolis offer lighthouse tours with a historically attired “wickie” (keeper) who spins humorous tales and mostly true historic stories. Specialty, dinner and wine-tasting cruises on the schooners Woodwind and Woodwind II also offer sail out of Annapolis.
The Hooper Straight Lighthouse, the third of its kind still in existence on the bay, once lit the way past Hooper Strait, nearly 40 miles south of St. Michaels. It was slated for demolition in 1966 when it was purchased by, and moved on-site to, the Chesapeake Bay Maritime Museum (CBMM). Visitors can tour the lighthouse, try out the clothes of a traditional keeper and swear the oath of an official Hooper Strait Light Keeper. C Street, the Carpenter St. Saloon, is a fun place to mix with the locals.
CBMM in St. Michaels hosts popular events such as the Antique & Classic Boat Festival ( June 13 to 15), Big Band Night ( July 5), Watermen’s Appreciation Day (August 10) and OysterFest (October 25). If serene sunset wine-and-beer- tasting cruises on a vintage catboat are more to your palate, the Selina II sails out of St. Michaels Harbour Inn & Marina.
Tilghman Island, long the destination for water fowling and fishing, now attracts seekers of a genuine Chesapeake experience related through the stories of the local watermen which have been captured by the Tilghman Watermen’s Museum. Visitors enjoy authentic tastes at the Tilghman Island Volunteer Fire Company’s annual Tilghman Island Day Seafood Festival featuring raw, stewed, steamed or frittered oysters, crabs, clams and more. A variety of games and demonstrations, including the crowd-pleasing workboat-docking contest, highlight the waterman’s lifestyle.
For another leisurely step back in time, stroll the tree-lined streets of Oxford with its charming historic homes, picket fences, taverns and unique shops. The Treasure Chest is overflowing with nautical gifts and local artist’s works. Get your licks in next-door at Scottish Highland Creamery, which locals repeatedly voted “Best Ice Cream on the Eastern Shore.”
On the banks of the Choptank River, Cambridge is one of the nation’s oldest colonial cities (1684). In his novel Chesapeake, James A. Michener modeled his fictional city, Patamoke, on the town. Its rich maritime history of building boats and catching seafood is outlined at the Richardson Maritime Museum and Ruark Boatworks. The Harriet Tubman Museum on Race Street is just a few steps from Black Water Bakery. Stop in for breakfast, lunch or a sweet before taking a cruise on the authentic oyster dredging skipjack Nathan of Dorchester.
Heading south along the bay, witness the towering Calvert Cliffs dominate 30 miles of Chesapeake shoreline. Megalodon Adventure Charters offers a treasure-hunting trip to search for over 600 known species of fossils lying along the banks. Paddle a few miles inland on their kayak and canoe trips up Parker’s Creek to discover one of the Western Shore’s most pristine and picturesque watersheds. The amazing history of Sharps Island Light, Cove Point Light, Drum Point Light, Hooper’s Island Light or Bloody Point Light is outlined on custom dinner cruises or lighthouse tours.
The Piney Point Lighthouse Museum houses a collection of four historic wooden vessels on loan: a 67-foot skipjack Joy Parks, an 84-foot bugeye Dorothy A. Parsons, a log canoe and a Potomac River dory boat, all focusing on watermen of the Potomac. A rare exhibit lying just offshore is the WWII U-1105 Black Panther. The VII-C German submarine was sunk in 90 feet of water by a Navy Explosive Ordnance Disposal team during WWII. In 1985, the U-1105 was “rediscovered” by sport divers and the site became the subject of an archeological survey expedition, and then Maryland’s first Historic Shipwreck Dive Preserve, which is intended to protect sites while making them open to the public.
Smith Island, only accessible by boat, is one of Maryland’s most unique cultural and ecological treasures. Besides crabs, the island’s bounty includes Maryland’s official state dessert, the celestial eight-layer Smith Island Cake, made with love at Smith Island Bakery. Ferries run seasonally from Crisfield and Point Lookout.
Heading south to Virginia’s Tangier, a low-lying island barely visible above the expansive bay waters, is home to a community of watermen and women whose ancestors have lived there since colonial times. The island has a fascinating history from the arrival of Capt. John Smith through the War of 1812. It is accessible only by ferry from Onancock, May to October.
Onancock’s art scene is unparalleled with renowned artists, artisans and craftsmen. The town’s name is derived from the Algonquin Indian word for “foggy place.” Linger over breakfast in The Blarney Stone Pub until the morning fog burns off the creek.
Cape Charles has recaptured its glory days as an 1886 Victorian railroad town. An upscale marina with shops and restaurants flank the northern side of town, while the south has a working harbor with transit docking. The Cape Charles Museum houses fascinating railroad memorabilia.
Hampton, VA, June 27 – 29
Top blues, soul, pop and jazz musicians perform at the Hampton Coliseum.
100th Annual Chincoteague Pony Swim
Chincoteague Island, VA, July 30
Majestic wild ponies populate Maryland’s Assateague Island and Virginia’s Chincoteague National Wildlife Refuge — and they can also swim! During the annual Chincoteague Pony Swim, the “Saltwater Cowboys” round up the ponies to swim across the Assateague Channel.
Piney Point, MD, August 2 – 3
A fun open house in recognition of National Lighthouse Day, Piney Point Lighthouse Museum.
Rock Hall, MD, August 8 – 10
A three-day pirate-infested party with performers, costumes and treasure hunts throughout the town.
Crisfield, MD, August 30 – September 1
Crab races, crab cooking/picking contests, entertainment, parade, fireworks and more in “The Crab Capital of the World.”
Annapolis, MD, September 13
Celebrating the perseverance, education and cultural heritage of the African Diaspora at the Navy-Marine Corps Stadium.
Susquehanna Wine & Seafood Festival
Havre de Grace, MD, September 20
Experience Maryland’s best seafood, top-notch live music and more on the grounds of the iconic Concord Point Light.
Salisbury MD, Sept. 19 – 21
A celebration of the roots, richness and variety of American culture featuring 250 of the nation’s finest traditional musicians, dancers, craftspeople and culture keepers.
Witches on the Water
Rock Hall, MD, October 24 – 25
Haven Harbour Marina Resorts hosts a spooky magical weekend where witches paddle the waters of Rock Hall.
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