Exploring the Eastern Shore by Sail

Many Reasons for Sailors To Visit the Eastern Shore

My love affair with the Eastern Shore has evolved over the decades. As a kid, the Eastern Shore was something endured during the bumper-to-bumper drive to Ocean City as our family went “downy oshun hon.” As a young adult, I was introduced to the charming towns of St. Michaels, Oxford, and Easton as destinations for weekend B&B stays or bicycling trips with friends. Cambridge was added later when I purchased a second home on nearby Hoopers Island for my family to get close to nature.

It wasn’t until I began cruising that I really explored these Eastern Shore treasures. It’s one thing to drive to these towns, but it’s another thing altogether to approach from the sea and sleep under their starlit skies. Here are a few of my favorites, including some that often escape notice.

st michaels maryland
A skipjack (sailing workboat) in front of the lighthouse at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland, on the Miles River off the Chesapeake Bay. Photos by Cheryl Duvall

Time-honored favorites

St. Michaels

I have sailed to St. Michaels more than any other Eastern Shore town. It is by far my favorite. We usually anchor in the outer harbor but occasionally reserve a slip at the enchanting Chesapeake Bay Maritime Museum (CBMM) where we are members, enjoying after-hours access to their grounds. At anchor, the view is ever-changing as many vessels pass, including 98-year-old Selina II and CBMM’s historic fleet. Each season we note the log canoe schedule and watch the excitement from our cockpit, sometimes inches away as they race through the anchorage.

Onshore, this quaint town has everything: casual and fine dining, coffee shops, bars and breweries, museums, art galleries, an abundance of shopping, inns, historic tours, a library, and chiming church bells. There are bikes and kayaks for rent, and we recently discovered a bicycle/walking path on the back side of town that winds past a playground and scenic marshes. On the practical side, boaters have access to a water taxi, dinghy dock, fuel, and several provisioning options. Rain or shine, St. Michaels delights me every season and is the place I usually take out-of-town guests.


My next favorite stop is the sleepier town of Oxford. I have a fondness for this charming village, and especially for the Oxford-Bellevue Ferry, the nation’s longest-running privately owned ferry. In the mid-80s, I took the ferry when bicycling with friends on a route that originated in St. Michaels. We’d always buy sandwiches at the Oxford Market on North Morris Street and eat them across the street in the waterfront park. Fast forward 40 years and I’m still able to follow the same rituals, but now can add hand-dipped ice cream from Scottish Highland Creamery.

We have always anchored in protected Tred Avon coves, about one and a half nautical miles away from town, except for one lucky night when there was enough swinging room for us in Town Creek Channel. Last fall we treated ourselves to dinner at the Robert Morris Inn after an afternoon of walking the town and idly watching boats sail past. The town bustles more during the summer due to events such as the Oxford Regatta (August 10-11) when the Tred Avon Yacht Club hosts multiple races including log canoes. Despite busier days, we always find the evenings to be blissfully peaceful at anchor.

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The author's sailboat Belle Bateau tied up at Oxford, Maryland, on the Tred Avon River off the Chesapeake Bay. 


About once a season we venture to Cambridge, often to meet with friends. With its ever-changing retail and dining opportunities, no two visits are the same. This is the only town on the Eastern Shore where we have never anchored. We usually tie up to the city wall which allows free dockage for up to 72 hours. Snapper’s Café is just 30 steps away, where 10 years ago we took a free slip with a dinner purchase. At the end of stately High Street, the yacht club and city marina offer a variety of slips and great views of Wednesday night races. From any of these slips, the historic town is a short walk and offers several restaurants, shops, and the Harriet Tubman Museum and Educational Center. Blackwater Refuge and the Tubman Underground Railroad National Historic Park are about 10 miles away and accessible by bicycle or Enterprise rental car.

Waters less traveled

Hoopers Island

Visiting Hoopers Island is not for the faint of heart. Deep-drafted vessels may have a challenging time navigating the Honga River and its tributaries. However, it’s worth the trip if you seek quiet coves and night skies without light pollution. We persevered because I wanted to dock at P. L. Jones Marina and dinghy to my second home on Upper Hoopers before it was sold. Yeah, I’m nostalgic like that.

The T-head was just barely deep enough for our 5.5-foot draft, though we did have to delay our departure by four hours to wait for high tide. During our stay, we rode bikes south across the scenic causeway through Middle Hoopers to the entrance of uninhabited Lower Hoopers. On the return ride, we re-provisioned at Fishing Creek’s General Store and had a delightful dinner at Old Salty’s Restaurant. Should you think about sailing to Hoopers, you’ll pass the recently sold Hoopers Island Lighthouse located at 38°15’22.5”N 76°14’59.3”W.

Sailboat anchored on the Eastern Shore of Maryland on the Chesapeake Bay. 

Smith Island/Crisfield

We have visited Smith Island a few times, though our draft is too deep to sail there ourselves. Although the pandemic affected tourism, it’s still a place you should visit before rising waters claim this unique three-town island of 238 residents. Slips are easily obtained in nearby Crisfield, and three passenger ferries make daily trips into Ewell for an afternoon visit. Bicycles may be taken or rented, and golf carts provide another option for exploring the marshy island. Before returning to Crisfield, don’t forget to enjoy Smith Island Cake, Maryland’s official state dessert. Tom Horton’s 2008 memoir “An Island Out of Time” sheds more light on this unique place. Indeed, you may be out of time if you delay a visit (find a recent article at proptalk.com).

On the way to or from

On your way to or from these destinations, be on the lookout for other delightful discoveries. We keep William Cronin’s “The Disappearing Islands of the Chesapeake” in our cockpit when passing shallow spits of land to learn about current and former islands. Some are being rebuilt with dredge, including Barren Island where I often daysailed from our home on Upper Hoopers.

Worthy of a detour, my favorite Bay sighting is the “ghost ship,” located between Smith Island and Point Lookout. In October 1966, the USAS American Mariner was intentionally grounded in 20 feet of water at 38°02’25”N 76°09’17”W. Since then, she has been used as target practice by Patuxent naval aviators. We have sailed near this rusted relic twice, once when departing Crisfield. While sailors aren’t allowed to get too close, binoculars and a good camera will stimulate imaginations about this scuttled ship that served all four branches of the US military. I love a good story and dream of writing about her one day.

Maryland’s Eastern Shore has much to offer, even for the seasoned Chesapeake Bay sailor. It may take a lifetime to fully discover her hidden treasures and scenic anchorages, only a few of which are mentioned here. And what’s not to love about that?

By Captain Cheryl Duvall

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