Cruising Chesapeake Bay

Cruising Destination:

Around 35.5 million years ago, a meteor roughly 3 miles wide slammed itself into the earth, right into what is now northeast America. This crater paved the way for over a thousand surrounding streams, creeks, and rivers to flow into its aftermath, impeding the regrowth of forests. Now, fast forward millions of years later to when the glaciers of the Ice Age had melted, and that’s when the modern-day Chesapeake Bay was formed. Today, it is one of the largest estuaries in the world, spanning over 200 miles long and 30 miles at its widest point. And depending on who you ask, it is arguably the top sailing capital of the United States — and most certainly renowned worldwide.

It is here that I found myself for a summer, along with my husband, aboard our 2008 Beneteau Oceanis 46, Shonto. In a time where the prospects of sailing to distant lands looked bleak, a journey to explore the northern shores

Chesapeake Bay

By Mandy Sorg

of my own country was, to me, still very much foreign – not to mention enticing, what with being farther from the threat of summer hurricanes. The deep blue waters of the south became a tannic brown, the palm trees had been swapped with maples and hardwoods, and white sandy edged beaches morphed into grasses, hills, and the occasional cliff. Having never cruised these waters prior, an extensive list of sailing destinations was made, in part by the recommendations of passing cruisers and the trusty internet. Being home to a multitude of must-see waterfront towns and cities, it’s near impossible for any cruiser to see them all in just one summer. So, in no particular order, except that of which the wind blew us first, Shonto set out for a tour of the bay, seeking destinations that can easily be visited within a few summer months.

ST. MICHAELS

In conversations, other cruisers gave their opinions on the Bay’s must-see locations, and when each would end their recommendations with a “…but my favorite is St. Michaels!”, you knew there must be something special about the place. As Shonto rounded the bend on the Miles River after a gorgeous 25 nautical mile spinnaker sail from Edgewater, the first sight of St. Michaels was of the Hooper Strait Lighthouse, standing guard on the edge of its harbor. Two cozy anchorages lie on either side of this screw-pile lighthouse, each a very short dinghy ride to the well-built public dinghy dock. St. Michaels, named after the town’s first church, dates to the mid-1600s. Its primary industry was building schooners, which were historically used to defend the Bay against British Navy attacks in the war of 1812. As a famous recount goes, St. Michaels was termed “the town that fooled the British,” for after hearing of impending attack, the townspeople hung lanterns in trees on the outskirts of town, tricking the British into cannonballing that area instead of the real St. Michaels. After the war, and with it a decline in shipbuilding, the town was revived via the fishing and, mainly, oystering industry. Today, it is a top tourist destination, with cottages tightly packed along streets adorned with English-like gardens, a main street teeming with shops and restaurants, and the stunning Inn at Perry Cabin (where the Wedding Crashers was famously filmed). Hammy’s Hideout, our frequented eatery – try the Thai chicken and adult milkshakes. And for those that enjoy a stiffer drink, there is a distillery, winery, and brewery all on the same block! At the Eastern Shore Brewing Company, I’ve personally discovered a new IPA favorite — the “F Bomb.” But it is the maritime museum that is the true must see. It is packed with such information, that it took two separate trips to see it all with any real appreciation. The museum had recently been awarded a $5 million contract from the state to build a working replica of a 17th century trading ship bringing European settlers to, what is now, Maryland. And at the time of my

visit, I was fortunate enough to witness the Maryland Dove’s frame being built entirely of wood, before its planned launch in 2021.

WYE ISLAND

Just five nautical miles northeast of St. Michaels is a hidden gem – the Wye Island Natural Resource Management Area (Wye Island, for short). The Maryland Park Services manages 2,450 acres of this 2,800-acre island for recreation, agriculture, and conservation purposes; and it is, in my opinion, the most pristinely beautiful spot in all of the Bay. Shonto meandered her way through the winding and picturesque Wye East River to anchor in the Dividing Creek, a still and quiet waterway nestling you in between its towering trees. But, be forewarned, there is zero cell service, though you shouldn’t be needing it anyway. There are endless outdoor activities offered within the island — hiking, biking, and even horseback riding. It houses a robust holly tree over 275 years old, six amazing trails you could explore for miles each day (some of which maze through orchards and cornfields), and is a haven for bald eagles and Canadian geese. If you want to watch the sunset with the most soothing (yes, soothing!) sound of Canadian Geese song, look no further. Our only distraction from nature was the occasional quiet crabber and a daily pump out boat were you to need one (which, might I add, I hold a great deal of appreciation for the Chesapeake Bay’s keenness and efforts on keeping its waters clean!). This solitude of nature was, hands down, the most difficult place to leave.

ANNAPOLIS

The city of Annapolis was notably the most encouraged city to visit in the Bay — it’s almost seen as a cruiser’s rite of passage to sail into Annapolis’ harbor. After weighing anchor in Wye Island, it was a glorious, smooth-water, 36-nautical mile northwest sail. (It also happened to be our anniversary, and a day in which I sailed in my wedding dress, because why not?). In my mind, the best option for a true Annapolis experience is to grab a mooring ball in its harbor. You’ll have an iconic view of downtown from your deck, and the dinghy dock at Kunta Kinte Park is a short ride away, putting you smack dab in the exact spot of downtown you want to be in. But please do be prepared for the ducks

here that will inevitably take your ride hostage while you’re away. First settled in 1649 by Virginian Puritans, Annapolis (named after Princess Anne, the heir to the throne at the time) was our country’s first peacetime capital. Now, it is the capital of Maryland, the United States’ capital of sailing (okay, arguably), and famously home to the United States Naval Academy. The city’s past is of huge political importance. There was the Annapolis Convention of 1786, the Treaty of Paris was signed here after the Revolutionary War, and it houses the oldest State House that, to this day, is still in legislative use — just to name a few. Everywhere you look, crabs, anchors, and Maryland flags decorate the streets in full parade fashion. Retail shops like Musto and Halley Hanson dominate the scene, and the smell of Old Bay Seasoning radiates through the air. Eateries are plentiful — might I suggest the crab dip at Harvest Wood Grill & Tap; the sushi and noodles at Joss Café & Sushi Bar; and the chicken and waffles at Iron Rooster. Once you’ve satisfied your appetite, there are many attractions to visit — the most popular being the State House, the William Paca House & Garden, the US Naval Academy, and the Banneker-Douglass Museum. But my personal favorite is to take a quick drive to Quiet Waters Park, to hike (or bike) the 340 acres of exceptional forest and meadows overlooking the Harness Creek and South River.

ROCK HALL

To sail anywhere north of Annapolis will inevitably require that you cross under the Chesapeake Bay Bridge. This bridge is a 4.3-mile long, 186-foot high suspension bridge — and the only one to span the width of the bay, connecting the western and eastern shores. After sailing 17 nautical miles northeast from Annapolis, we arrived at Rock Hall, a town nicknamed The Pearl of the Chesapeake. Instead of getting a slip in the harbor, Shonto was comfortably moored in Swan Creek, a very narrow waterway quietly tucked away just north of the harbor. Rock Hall is a quaint fishing village with a population just over 1,300. Staying here feels like stepping back in time, or at least slowing down, and has an atmosphere unlike any I’d seen elsewhere on the bay. The harbor has delicious seafood restaurants, including the famous Waterman’s Crab House where you can get (you guessed it) fresh-caught jumbo Maryland crabs. On the streets surrounding the harbor stand many well-kept houses, quiet and still, with the only noise coming from the playing school children

nearby. Shops and a local music venue occupied the main street, and the best coffee shop in town, Java Rock, sat just at the end where you could sip your coffee under the shade trees while listening to the sounds of church bells ringing beside you. But there is more to Rock Hall than their small-town charm. Each August, cruisers and land-lovers of all ages descend on the city for the main event, Pirates & Wenches Fantasy Weekend, a three-day long, vibrantly celebrated pirate invasion.

SOLOMON’S ISLAND

Roughly 45 nautical miles southwest of Rock Hall lies the town of Solomons Island on the very tip of a peninsula. Shonto was cozily anchored in Mill Creek, where each night we were treated with gorgeous sunsets. Originally settled and named Bourne’s Island in the mid-1600s, the land was later purchased by a Baltimore businessman, Isaac Solomon, in the 1860s, from which the town now gets its name. Solomon, understanding how significantly well protected the surrounding waters were, established a shipyard and fishing fleet of over 500 vessels by 1880. The island has since stood as an active maritime and oystering location. But, perhaps one of the most notable maritime relations was during World War II, when the Navy chose the island to be its training site for amphibious operations. Today, it is a popular weekend destination, particularly within the boating community. Whether you’re heading north or south from the ICW or ocean, Solomons is an excellent midway stop within the Bay, and a pleasant town to relax in. The island has a long and easily walkable boardwalk to the west, where you can read the accounts of historical naval activities, and to the east the street is lined with shops, excellent local restaurants, a tiki bar, and a plethora of marinas. To the north, there is the beautiful, and not to be missed, Annmarie Sculpture Garden, a family-friendly forested park displaying work from renowned sculptors and artists. -----------------------------Though my first summer visit to the Chesapeake Bay only held a handful of locations, that’s partly one of the wonderful things about the Bay. You see, it is just so incredibly large, with so many worthy places to see, that there is just no way you can visit them all, in any true appreciative manner, in just one cruising season. Year after year, it is a place that can bring more exploration than the last. There is an abundance to explore, from the sweet, quiet town of Galesville, the crab cook-offs of Cambridge, and the disappearing land of Tangier Island. And what better way to explore the special gems of the Chesapeake Bay, just as so many did in its past, than by the sea?