The Great Chesapeake Bay Loop

by

The most ambitious nautical adventure in the Bay takes sailors to a potpourri of iconic Maryland towns and experiences

The Chesapeake Bay is an extraordinary natural resource, teeming with life and getting healthier by the day. Simply put, the Bay is an exquisite ecological wonder. 

This immense body of water (more than 18 trillion gallons, according to the Chesapeake Bay Foundation) is a veritable playground for residents and visitors who enjoy all sorts of water sports, as well as those who have the pleasure of experiencing it from shore. 

The Bay is a boater’s paradise—about 200 miles long, reaching from Havre de Grace, Maryland to Norfolk, Virginia. Navigating that round trip, whether under power or sail, is called the Great Chesapeake Bay Loop. 

Making the entire journey of the Loop requires a great deal of time, resources, maritime training, along with a generous spirit of adventure. For those of us who aren’t able to embark on such a voyage but long for an authentic Chesapeake Bay experience, we’ve done some research, talked with experienced captains, and selected our “must-see” spots on both shores of Maryland’s portion of the Loop (plus, one stop in Virginia), whether you visit by water or land. 

Let’s start our trip around the Bay in Calvert County at the mouth of the Patuxent River…

Solomons

You’ll find Solomons Island to be historic, charming, and inviting. Book your stay at Solomons Victorian Inn which has stunning harbor views. After you drop your bags, a visit to Calvert Cliffs State Park is a must do. Take the Red Trail and hike 1.8 miles to the sandy beach where you can hunt for shark teeth and other fossils. Book a dinner cruise on a 40-foot sailboat with Chesapeake Bay Charters and watch the sun slip below the watery horizon. Before you leave Solomons, go to the Annmarie Sculpture Garden & Arts Center where you’ll stroll past sculptures on loan from the Smithsonian. The center hosts festivals, exhibits, classes, and family activities. 

Herring Bay

North of Solomons is where you’ll find the Rose Haven, Fairhaven, and Deale harbors in Herring Bay. Captain Jayne Durden thinks it’s one of the loveliest spots around. Originally from Melbourne, Australia, Durden fell in love with the Chesapeake Bay when she relocated here 10 years ago. She now trains female sailors, delivers boats, and cruises and races her Beneteau 331 Happy Place. 

“We often do a quick sail in Herring Bay after work and then anchor up near Fairhaven for the night,” Durden says. “Tucked inshore of the entrance channel to Rockhold Creek, Fairhaven gives you a pretty place to anchor with a view of the cliffs and quaint homes. The water is 8 to 10 feet deep right up in under the cliffs and up to the swimming platform in the little bay. During the spring and fall, it’s a good place to swim before the jellyfish move in. And on the Fourth of July, it’s the best place to watch the Rose Haven fireworks display.”

Durden says that Deale—a small town with a big heart—is worth a visit and has excellent waterfront restaurants: Skippers Pier, Dockside, and Happy Harbor. “A water taxi will take you around the creek or you can easily go by dinghy or kayak. Whether you want an amazing anchorage, a resort-style marina, or a nice small town, come to Fairhaven and Deale.”

Baltimore

Moving northward on our loop, we come to the Baltimore area, a favorite spot for Captain Julianne DeGraw Fettus. She has been boating on the Chesapeake since 1987 and has been sailing since she was quite young. While she doesn’t live aboard her Cherubini 44 ketch (a two-masted sailboat), she does spend most of her free time aboard. When asked about the places she loves to visit, Fettus says, “The Bay is such an amazing place with so many personalities—it’s hard to narrow it down. The Anchorage Marina in the Canton area of Baltimore is one of my favorite places when I’m up for the hustle and bustle of the city. The dockmaster and staff there are friendly, plus there are lots of restaurants nearby as well as grocery stores, a West Marine, and many other amenities within easy walking distance.”

Choose this site if you have time to spend wandering around on land. In addition to easy access to the Inner Harbor and the opportunity to marvel at picturesque sunsets, when you dock here, you’re only a half mile from historic Fort McHenry. 

Head of the Bay

Havre de Grace is a little town way up in Harford County where the Susquehanna River empties into the Bay—a beautiful spot for boaters and day travelers alike. Discover the art of making decoys at the Decoy Museum. If you’re a fan of lighthouses, take in the views from the Concord Point Lighthouse. Get a table at MacGregors—located in the iconic bank building—and enjoy lunch or dinner while you watch the boats go by.  

Rock Hall & Chestertown

We’re heading south now to the Eastern Shore which has its own, distinct character. Want to go fishing? Call Captain Wayne Gatling of Rock Hall in Kent County. He is an experienced guide who captains a 46-foot Markley—a traditional Eastern Shore semi-deadrise workboat. He takes groups fishing for striped bass (Maryland’s official state fish, known locally as rockfish), catfish, white perch, and bluefish from June through October. He provides all the bait and tackle. All you have to bring is a cooler (and sunscreen, of course!). 

“Over the last 50 years, I’ve taken more than 7,500 fishing charters in Maryland (and 2,500 in the Florida Keys) and I make sure that each person enjoys their time on the Bay,” Gatling says. “Even if you’ve never fished before, we’ll get you all set up and you’ll love it. We clean the fish and it will be bagged and ready when you get off the boat. Take your catch to Waterman’s Crab House and they’ll cook it for you. Doesn’t get any fresher than that!”

While you’re in the area, take a kayak excursion with the folks from the Sultana Education Center in Chestertown. Paddle along the Captain John Smith Chesapeake National Historic Trail to see wetlands, native wildlife, and spectacular views. Kayaks, paddles, and life jackets are provided. 

Let’s Go Crabbing! 

There’s nothing like dipping crabs from a trotline for a true Eastern Shore experience. If you plan to be in the Kent Island area between mid-July and the end of October, book a trip on The Marylander. It’s docked at the Kentmorr Marina in Stevensville. Stay at the nearby country house called Kent Island Resort but be advised—you have to get up pretty early to go crabbing! 

Oxford

A little farther south is a secluded spot that Captain Fettus recommends for a quiet getaway. “The Cutts & Case Shipyard in Oxford is home to beautiful wood boats representing the golden age of sail. The amenities are basic because it’s a working yard so you will hear sanders running in the morning, but I enjoy that.” 

Fettus says, “Strolling around the town and enjoying the architecture is the extent of things to do unless Tred Avon Yacht Club is hosting an event. The Heritage Regatta and the Log Canoes Race in August are fun to watch.” 

Stay at the historic Robert Morris Inn. Built in 1710 by founding father and Declaration of Independence signer Robert Morris, George Washington was known to stay there. It’s also where James Michener wrote the outline for his book, Chesapeake.

Cambridge

Continuing our travels, we land in Dorchester County. If you love history, stop at the Harriet Tubman Underground Railroad Visitors Center in Cambridge. If you arrive by boat, Captain Durden offers this bit of inside information: “Tucked away in the Little Choptank is a glorious anchorage in the mouth of Hudson Creek. It’s protected by a tiny spit of land to the west with enough space for about 10 boats to comfortably anchor. We shared the spot with three boats in a flotilla and were serenaded by their lovely sing-along. It was great holding: no passing traffic to worry about wake; idyllic and peaceful. The next morning, we motored up the creek a bit, admiring the sweeping lawns of stately homes.”

Crab Capital of the World

Crisfield is the next stop on our virtual loop of the Chesapeake Bay. Stay at the sea captain’s manor house, Lady Grace, a bed and breakfast in the historic district. Dine at Fisherman’s Grille. On the weekend, call The Crab Pot Depot for the best shrimp (takeout only). Hop on a boat to Smith Island to get the Maryland state dessert: a delicious Smith Island Cake. And you’ve got to experience the world-famous Crab & Cruise® at the Crab Place: an all-you-can-eat crab feast followed by a dance party cruise on the Bay. 

Onancock

The southernmost point of our journey is where you’ll find Kristin Bishop. She is a pioneer: one of the first women in the Navy assigned to fill sea duty billets aboard a ship. An experienced boater who has explored much of the southern Bay, she graciously offered insights from her travels. “Onancock, Virginia, is a favorite place to visit by boat because of the friendly atmosphere and welcoming locals,” Bishop says. 

Cruise up Onancock Creek which, according to Waterway Guide, “lies almost 20 nautical miles southwest of the mouth of the Pocomoke River and about five nautical miles southeast of Watts Island.” The creek is a beautiful, deep tributary that is well marked. When you arrive at the town dock, it’s only a short walk up the hill to get to town. 

Bishop says that the Onancock Wharf and Marina offers updated facilities as well as a free dinghy dock for those who prefer to anchor out. “The marina offers a courtesy car as well as a list of residents who offer local rides to those who visit by boat.” She went on to say that many restaurants have outdoor seating and are dog-friendly. 

If you like old houses, you’ll love this little town. “Onancock dates back to the mid-1600s. The homes in the historic district display an impressive variety of architectural styles. It’s always a pleasure to wander through the town and admire the beautiful homes and gardens,” Bishop says. “I also enjoy the parks, local galleries, and museums.” 

That completes our amended tour of special places along the Great Chesapeake Bay Loop. There is so much to see and do that you’ll definitely want to make time to explore this miracle of nature and the many towns that dot its shoreline. 

Learn more about Maryland’s portion of The Great Chesapeake Loop at: visitmaryland.org/unique-experiences/chesapeake-bay-loop.