Maryland's Eastern Shore: Sailing Secrets and Hidden Havens on the Chesapeake Bay
Maryland's Eastern Shore, a hidden paradise nestled along the shores of the Chesapeake Bay, is a sailor's dream waiting to be explored. Away from the well-trodden paths, Shardana Sailing Charters invites you to uncover the hidden gems that make this region a unique maritime sanctuary. Join us as we set sail on a journey of discovery, unveiling the secluded coves, charming towns, and unspoiled beauty that define the enchanting Eastern Shore.
Cambridge:Cambridge, Maryland, is a historic city located on the Eastern Shore of Maryland, nestled along the Choptank River. Like many towns in the region, Cambridge has a rich history dating back to colonial times. It played a significant role in the maritime industry and served as a bustling port for trade and commerce. Cambridge holds historical significance as a focal point in the life of Harriet Tubman, the famed abolitionist and conductor of the Underground Railroad. Tubman was born nearby and later returned to the area to lead enslaved people to freedom. Visitors can learn about her legacy at the Harriet Tubman Underground Railroad Visitor Center.
Cambridge's downtown area features historic architecture, quaint shops, art galleries, and waterfront restaurants. Visitors can stroll along the streets, enjoy waterfront dining, or browse local boutiques for unique finds. The Dorchester County Historical Society operates several historic sites and museums in the area, offering insights into the region's diverse history and cultural heritage.
Oxford: Maritime Charm and Tranquility Oxford, founded in 1683, is a quaint town on the Tred Avon River. Tied to the watermen's legacy, Oxford exudes a peaceful atmosphere that invites sailors to relax and enjoy the simple pleasures of the bay. Oxford is home to the oldest privately owned working ferry in the United States. It is called the Oxford Bellevue ferry. The ferry takes passengers, cars, bicycles across the Tred Avon River between Oxford and Bellevue landing cutting off significant travel time by car from Oxford to St. Michaels. Oxford has a wonderful water-front park where one can spend a few hours picnicking or just relaxing.
This town is the opposite of St. Michaels but with the same amount of charm and quieter. Oxford holds an annual Picket Fence auction where people can bid on picket fence artwork. Each year local artists paint small sections of a picket fences to be auctioned off to raise money for local non-profit groups.
While other waterfront towns have succumbed to waterfront condos and glitz, Oxford has retained its historic charm. The tourism and leisure activities are fueled by people’s desire for laid back living , fresh air, summer breezes, and a haven from the hustle and bustle of city life. Explore the charming streets, dine in fabulous restaurants, and experience the tranquil beauty that defines Oxford, Maryland.
St. Michaels: Maritime Heritage and Beyond St. Michaels is located along the Miles River. While St. Michaels is a well-known destination, it harbors hidden corners that reveal its true charm. Beyond the bustling waterfront, venture into the quiet streets lined with historic homes and boutique shops. St. Michaels boasts a well-preserved historic district with beautifully restored colonial-era homes, charming shops, galleries, and restaurants. The streets are lined with colorful flowers, and the architecture reflects the town's rich heritage. The Chesapeake Bay Maritime Museum, located in St. Michaels, is a focal point for visitors interested in the region's maritime history. It features exhibits on boatbuilding, crabbing, oystering, and other aspects of Chesapeake Bay's maritime heritage. Visitors can explore historic boats and demonstrations. Shardana Sailing Charters is a member of the Chesapeake Bay Maritime Museum which allows us to dock overnight at the museum thereby allowing our clients to have it to themselves in the evening. Wine enthusiasts can visit the St. Michaels Winery to sample local wines produced from Maryland-grown grapes. The winery offers tastings and tours, providing a delightful way to experience the flavors of the region. In addition, St. Michaels has its very own award-winning rum distillery, Lyon Rum where you can have a rum tasting and tour the distillery. Overall, St. Michaels, Maryland, offers a delightful blend of history, natural beauty, and coastal charm, making it a popular destination for Shardana’s guests seeking a relaxing getaway by the water.
The Wye River and Wye Island Natural Resources Management Area, Nature's Sanctuary: The Wye River is a pretty magical place. A good number of people pass it by without giving is a second thought as it is tucked out of the way to other destination spots. For sailors yearning to reconnect with nature, Wye River is a hidden sanctuary offering pristine landscapes and abundant wildlife. It connects to the Miles River just south of Eastern Bay. There are countless Inlets and coves tucked around the Island providing secure anchorages all over the area.
Entrance to Shaw Bay and the Wye River
One of the notable features of Wye Island is its rich history. The island has been inhabited for centuries, with evidence of Native American settlements dating back thousands of years. Later, European settlers established farms on the island, and remnants of these historic structures can still be found today. The Wye Grist Mill or the Wye House has historical ties to Frederick Douglass. One of Marylands most historic landmarks, the Wye River Plantation, was the home of William Placa, the third governor of the State of Maryland and a signatory to the Declaration of Independence. The property was donated to the Aspen Institute and with the help of Paul Newman (the actor) became its main conference center. In October 1998, The Wye River Accords, an agreement between the Palestinian Authority and Israel was signed. This agreement was supposed to implement the 1995 Oslo Accords creating a Palestinian State adjacent to the State of Israel living in peace. Not many people realize marylands eastern shore is involved with world affairs!
Along the Wye and the Wye East Rivers you’ll find many of the views for which the Chesapeake is famous: habitat for waterfowl and other native wildlife, flora varying from marshland to stately old trees, as well as the sweeping slopes of carefully manicured lawns leading up to mansions on hilltops. The Wye River is a great place to fish, crab, swim and explore. Once Shardana is anchored, we often take in the fresh air and the quiet of the space. You can jump in for a swim and of course go and explore. It is easy to hop into our dinghy to explore the nooks and crannies of the river or head to Wye Island for a hike or to relax on one of its secluded beaches. Wye Island is valued for its natural beauty and ecological importance. The area serves as an important habitat for migratory birds, including waterfowl and songbirds Wye Island is a true haven for those seeking solitude amidst the beauty of the Chesapeake Bay.
Chestertown Waterfront Park
Chestertown: Colonial Elegance While sailing along the Eastern Shore, Shardana clients can take a detour up the Chester River and discover the hidden elegance of Chestertown. Stroll through the brick-lined streets and the beautiful riverfront, visit the Washington College campus, and enjoy the many local eateries. The Schooner Sultana, an education ship, makes its homeport in Chestertown.
A gem along the Chester River, Chestertown is a town steeped in colonial history and brimming with architectural beauty. Chestertown has been serving as the Kent County’s seat of government since 1706. It was a Royal Port of Entry while under British-colonial rule. Inspired by the Boston Tea Party. Chestertown had its own tea party in 1774 in response to the British Tea Act. Members of the local chapter of the Sons of Liberty were outraged by the taxes on tea and local leaders adopted the Chestertown Resolves, making it unlawful to buy, sell, or drink tea from England. When word came that a recently arrived brigantine, a type of ship, named the Geddes held tea, a small group of men forcibly boarded the ship and threw the tea into the river. Unlike in Boston, this event supposedly occurred in daylight and the men wore no disguises. The Chestertown Tea Party Festival commemorates the event annually every Memorial Day weekend. Chestertown has The Cat Colloquium . The Cat Colloquium is a 501c(3) non-profit organization dedicated to creating a community that advocates for animals and children in a warm, friendly, and inquisitive way by caring for and providing a home for their resident cats who welcome visitors to their warm, safe, and creative environment. Chestertown has a wide variety of wonderful restaurants to fit every taste and budget. Chestertown is a quintessential eastern shore town.
Rock Hall: Waterman and Sailing Village Nestled along the tranquil shores of the Chesapeake Bay, Rock Hall, Maryland, is a picturesque waterfront town that embodies the quintessential charm of the Eastern Shore. With its rich maritime heritage, stunning natural beauty, and vibrant community spirit, Rock Hall offers a delightful escape for visitors seeking relaxation, adventure, and a taste of coastal living. In Rock Hall you will be greeted by sweeping vistas of the bay, dotted with sailboats. Beyond its maritime allure, Rock Hall boasts an array of attractions and activities to suit every taste. Nature enthusiasts will delight in the abundance of outdoor adventures, from kayaking and paddleboarding along scenic waterways to birdwatching amidst the lush marshlands of Eastern Neck National Wildlife Refuge. You can Bike anywhere in in around Rock Hall and its nearby beachs beckon sun-seekers to relax and unwind. People congregate to watch some of the best sunsets on Chesapeake Bay at this beach.
Visit the small yet informative Rock Hall Museum to learn about the town's maritime heritage and its role in the oyster and crabbing industries that have sustained generations of residents. Whether you're seeking a peaceful retreat in nature, an adventure on the water, or simply a taste of small-town charm, Rock Hall, Maryland, invites you to experience the beauty and hospitality of the Chesapeake Bay region. With its welcoming community, scenic landscapes, and endless opportunities for exploration, Rock Hall is sure to capture your heart and leave you longing to return again and again.
Maryland's Eastern Shore on the Chesapeake Bay is a sailor's paradise filled with hidden gems waiting to be discovered. Shardana Sailing Charters invites you to set sail on a journey that goes beyond the well-known ports, revealing the true essence of this maritime haven. From historic towns to secluded retreats, each hidden gem along the Eastern Shore adds a layer of magic to the sailing experience. Join us as we navigate the waters and uncover the secrets that make Maryland's Eastern Shore a destination like no other. Click here to find out more about Shardana Sailing Charters or to book your sailing getaway today.