9 Small Towns In Chesapeake Bay To Visit For A Weekend Getaway
The Chesapeake Bay is the largest estuary in the United States and a popular spot for vacationers. For centuries, even before the arrival of Europeans in the early 1600s, the Chesapeake Bay was a source of food and sustenance to the native tribes who called the land their home. In fact, the bay gets its name from the Chesapeake Tribe Nansemond and other Algonquine-speaking peoples.
The water is brackish in some areas, which is ideal for sea creatures like oysters (a popular dish in the region). The main source of fresh water to the bay is the Susquehanna River, which flows down into the Chesapeake from the north in Pennsylvania. While the natural features of the area are impressive, it's the small towns dotting its boundary line that really make it a memorable place to visit. These little towns have lovely hotels, chic shopping centers, and unique landmarks, which will make any weekend getaway unforgettable.
Cambridge, Maryland
Cambridge is a charming little town that sits along the Choptank River, a tributary river of the Chesapeake Bay. This waterway is an important part of the state's natural beauty and habitat, serving as a home to several fish species and unique varieties of oysters. The Eastern Oyster (Crassostrea virginica) is the most common breed of oyster found in the Choptank, although its population has declined over the years, with nearly 69% of its natural habitat destroyed. Fortunately, conservation efforts help sustain the creature's population. For those who enjoy exploring Maryland's fascinating wildlife, Cambridge is an excellent place to start since it's within close proximity of the Sandy Hill Sanctuary, a wildlife sanctuary designed to preserve the state's water species.
However, travelers who prefer to stay on dry land need not worry since the region has no shortage of fascinating spots worth exploring. There are several nature trails, including the Little Blackwater Soft Launch and Water Trail in the south of town, which takes trekkers on a wonderful tour of the Blackwater River and the Little Maple Dam Branch. There are also several outdoor sites in the north and central parts of the community, but Long Warf Park certainly gives the best views of the surrounding Choptank River. Not far from this location is the Harriet Tubman Museum and Educational Center, where locals and visitors alike celebrate the legendary liberator's contributions to her home state and her impact on American history.
Cambridge is an excellent place to experience world-class Southern-style dishes. Restaurants like Lil' Bitta Bull is one of the best locations in the area for cornbread, brisket, pulled pork, and more. The friendly atmosphere gives newcomers a sense of belonging while they pass through for the weekend. As a favorite place for visitors seeking a quiet yet adventurous getaway, Cambridge has plenty of hotels available for guests. The Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina along the water is definitely the top choice since it has some of the loveliest rooms and one of the best views of the water.
Deltaville, Virginia
Deltaville is an adorable, census-designated town located on the eastern tip of the county of Middlesex, Virginia. Deltaville touches the Chesapeake Bay, with the Piankatank River flowing into the bay from the west and touching the town to the south. Its position along both of these bodies of water makes Deltaville an excellent spot to visit for those who enjoy boating and watersports. Places like Safe Harbor Stingray Point and Nomad Norview Marina give visitors views of the local shipyards and boats docked along the shore. Both serve predominantly as docking sites for locals and guests seeking to keep their ships safe and clean, as well as a launching point into the bay. Travelers who own a ship or have a love of the open water should definitely check out these locations.
Two stunning land sites visitors should visit while in the area are Stingray Point and Stove Point Neck. Both places sit along the water, offering wonderful views and spectacular nature hikes surrounded by the local wildlife and plant life. Engaging in the local beach worship and spiritual gathering with the Zoar Baptist Church might be a great way for some to have a deeper connection to the surrounding waters through the morning beach services. The River Retreat Campground on Timberneck Road and Cross Rip Campground are lovely spots for a quiet camping experience in the woods and a good choice for those seeking an immersion in nature. In particular, Cross Rip Campground prides itself in offering a rustic and old school camping time, with the Chesapeake Bay just a few minutes away.
The Deltaville Maritime Museum is a fantastic spot to start learning about the town's history and enjoy a little step into the past. The museum's displays include informative pieces about the Delmarva meteorite of 35 million years ago and exhibits showing the early shipbuilding of the region. Just a half mile from the museum is the decadent Deltaville Tap and Raw Bar. Visitors can indulge in locally sourced oysters, crab claws, and other fresh seafood at this seaside location. While there are plenty of campgrounds in town to make for a spectacular weekend away from home, the Deltaville Dockside Inn is an adorable little place for a more comfortable experience.
Crisfield, Maryland
Crisfield is a patriotic and welcoming little town located just over an hour south of Cambridge. The land is often called the "crab capital of the world and is a haven for fishing and crabbing alike. The town's natural beauty is matched only by its adventurous atmosphere that permits visitors to enjoy the lovely harbors and bays connecting the community to the Chesapeake waters. There is Somers Cove Marina for those who appreciate boats and other maritime vessels and is the gateway to the sea for those looking to spend some time on the waves.
The marina offers rentals that guests can take out on the water. Those who prefer to stay on land while getting excellent views of the waters can use the local pavilion for a personal celebration or event. The Crab Place restaurant sits just a few minutes away and serves crab claws, fresh lobster, crab cakes, and much more. It's a great place to visit to get an authentic taste of the town and bay. Crisfield City Dock, which sits right along the Chesapeake Bay, definitely gives spectacular views that are very photogenic and great for travelers who want to share some pictures on their social media.
Despite this town's small size, there are lots of hotels and lodging options for tourists to stay and feel refreshed after a long day at sea. Captain Tyler Motel is the most popular place to stay for those on a budget. Even though this site has some great prices, the two-story building houses clean and comfortable rooms. For those who wish to book their stay in advance, the motel offers further savings for those who reserve their stay in advance. There's also the slightly more luxurious yet still affordable site of Rodeway Inn at Somers Cover Marina. The hotel's location near the water means guests can enjoy a better view of the water.
Gwynn, Virginia
Gwynn is a community based on the lovely Gwynn Island of Virginia, approximately thirty minutes from Deltaville. It's the idyllic place for anyone who wants an immersive experience in the Chesapeake Bay since the site is surrounded by portions of the larger bay known as Hills Bay and Wharf Creek, among others. These smaller portions of the bay offer excellent times on the sea, surrounded by the island's natural charm.
Those who want to learn a little about the culture and history of the island should check out the Gwynn Island Museum. The museum, though small, stores a vast body of the town's past so all can appreciate it. The house, which serves today as a museum but acted as the island schoolhouse before this, is itself a historical location dating back over 100 years. The two-story house keeps important items like prehistoric fossils and colonial artifacts from early settlers, including old tools, weapons, and clothing. The Hatchery is a local oyster eatery that gives guests a tasteful experience of locally sourced seafood. Each dish gets served in traditional street food fashion off the back of the food truck, so be sure to drop by during the warmer seasons when they're open for business.
Just across the way on the mainland is Sea Farm, a gorgeous seafront ranch that specializes in harvesting and cultivating the bounties of the ocean. Anyone hoping to get some delicious seafood in bulk or who desires to learn more about the seafood industry should be sure to visit. There aren't many options for stays like hotels or lodges, but Sun Retreats meets all the needs of tourists visiting the island. This RV park isn't just for those who enjoy camping out under the stars in a tent, or who own an RV to stay in while at the campground. Sun Retreats also has vacation homes for rent that create a comfortable and homey experience while exploring Gwynn Island.
Urbanna, Virginia
Just about thirty minutes north of Gwynn Island is the ocean front town of Urbanna. The town touches Rappahannock River, which flows directly into the Chesapeake Bay, which served as an important watery shipping lane back in the day. This waterway is still an important part of the town's history, culture, and economic development, with some joking that the town has more boats than people. The community traces its roots back to its official establishment by an act of assembly in 1680, and the region's fame as an export site of tobacco continued growing.
Urbanna is proud of its heritage and shares its history freely with all who wish to see it first-hand. That's why the town commissioned the creation of the HP Reveal App, which allows users to participate in an immersive self-guided tour of the town's historical portions. Just by downloading the app and scanning the various structures, visitors can learn all about the different old homes, some of which are on the National Register of Historic Places. The top locations include the Scottish Factor Store, built in 1766, and the Bristow Store, built in 1896.
Spending several hours previewing the beautiful history of the oceanfront town is sure to work up an appetite. The area has several eating establishments, like Where the Sidewalk Ends, a cozy local cafe, or Portside Grill On Urbanna Creek, where visitors can indulge in cocktails and wonderful foods. The Chesapeake Inn is an adorable and elegant place to refresh and rest while having fun on a weekend getaway. The inn's twelve bedrooms are accommodating and include fast Wi-Fi, microwaves, and cable TV. Tourists planning a romantic weekend along the shores of the Rappahannock River will surely love this cute establishment.
Saint Mary's City, Maryland
Saint Mary's City shares its name with Saint Mary's River, which connects the historically significant community to the Chesapeake Bay. The town traces its European history back to its founding in 1634 when it was settled by Catholics seeking freedom from religious persecution back in the Old World. It was an important port city for shipping goods like tobacco from Saint Mary's City to Europe. This trade made the region relatively wealthy, and later, it became the first capital of the state of Maryland.
The historical village located in the southern parts of the area has intact historical spaces, homes, and other structures from the community's early days. The remnants of the old Brick Chapel go back to its founding in 1667 when the first church was erected, which is where early settlers gathered in worship. Archaeologists even found lead coffins and other artefacts of the early years in the church's foundation. However, those who hope to see more of the city's nautical past should spend some time exploring the Maryland Dove.
The Maryland Dove is a beautiful reconstruction of one of the city's founding ships. The town was settled by colonists traveling on board the Ark and the Dove. The Dove was almost lost in a storm as it traveled to the New World but managed to arrive at the coastal colony after some struggle. The modern reconstruction strives to recreate the Dove as accurately as possible based on sketches and other data that's available. Those hoping to spend a few days, which is recommended because there's so much to see, should consider staying at the nearby Inn at Brome Howard. This charming little spot sits just a few minutes outside of town to the south and is a quiet spot worth booking for a few nights' stay.
Oxford, Maryland
Oxford is an adorable little seaside town situated about two and a half hours northeast of Saint Mary's City. The city is located along the Tred Avon River, which connects to the Chesapeake Bay to the south via the Choptank River. Oxford has the enviable position of being the oldest town in Maryland, with an official establishment date of 1683. However, most experts believe that the town's unofficial founding began about twenty years earlier. For about a hundred years, up until the Revolutionary War, Oxford was an internationally recognized shipping port city along the Chesapeake.
Its old age and international prominence mean that Oxford has a lot of unique history tied to its roots. There are lots of ways tourists and those on a weekend excursion can see and experience this region's extensive past, including the Oxford Museum and the Waters Edge Museum. Oxford Museum is a small structure that stores a surprising number of local pieces of memorabilia and photographs of the town's early years. The museum also hosts events every year, like the Memories and Musings Program and exhibitions of local artists during the holiday season. The Water's Edge Museum also celebrates the community's history, showcasing and highlighting the African Americans who helped make Oxford what it is today.
While at the Oxford Museum, consider picking up a map of the painted picket fence for a walking tour of the city. These lovely white fences show off the talent of the town with images of flowers, insects, and natural beauty. Cycling enthusiasts can also tour the coast and open landscape on the Oxford/Saint Michaels Bike Path. This path is well-known as one of the best in the region and takes visitors on a stunning tour of the town and nearby areas. It's the perfect weekend activity, and after long days outside seeing all there is to offer, consider checking in to the adorable Oxford Inn and dining at the historic Robert Morris Inn.
Tilghman Island, Maryland
Just under an hour to the west of Oxford is Tilghman Island, a historical location with a reputation for being a prime place for vacationers. The island sits directly within the Chesapeake Bay, with Maryand's Harris Creek flowing into the bay to the east. Tilghman Island became part of Talbot County in 1707, but the region was settled long before this date when it was known as Great Choptank Island. It was later known as Foster's and Ward's Island, but after Matthew Tilghman inherited the land from his family, the island became known by his family's last name.
Tilghman Island is home to the Tilghman Watermen's Museum, which preserves the ship The Kathryn and other important pieces of the past. The site also stores models of ships and paintings, which are exciting local artistic items. Anglers and those who enjoy the open water will feel right at home in this small town. Folks can book an open water experience on board the Chesapeake Lady II Fishing Charters, which provides an exciting time fishing on the bay, with bait and tackle included. History buffs can visit the bridge at Knapps Narrows. Although not the original structure, this bridge, which connects the island to the mainland, has existed since the 1600s and is a good spot for pictures.
With so much to see and enjoy, guests to town may want to plan a few days stay at one of the city's tranquil inns. The Black Walnut Point Inn is one of the most popular inns with an untouched appearance. This inn sits in a very secluded and peaceful spot on the southerly tip of the land, affording spectacular views of the water. The small town also has a few delicious restaurants offering their guests wonderful, fresh-caught seafood.
Cape Charles, Virginia
To the southeast of Deltaville and Gwynn Island, across the Chesapeake Bay, is the cute little town of Cape Charles. In addition to the Chesapeake Bay, the town is flanked by Longs Pond to the east, creating a nautical and calming vibe in the area. A seven-foot-tall statue of the Roman god Neptune stands near the shore with a sea turtle in his hands, amplifying the city's overall sea-themed atmosphere and is a must-see attraction. To the locals, this site is also a handy landmark, helping to aid in the general direction of the layout of the community.
To preserve, celebrate, and showcase the community's heritage, the Cape Charles Historic District exists near the northern portions of town. The nearby Cape Charles Museum and Historical Society is the best spot to learn and see the city's fantastic past. The museum has indoor and outdoor exhibits to explore, including train stations and old locomotives. Additionally, the Cape Charles Rosenwald School, also known as the Cape Charles Colored School, stands as a symbol of African Americans' early lives and growing rights in the region. The Concerts in the Park program encourages residents and visitors alike to gather around the pavilion found in Central Park in the historic district, where local bands and musicians provide free performances.
The town houses a vast array of natural and wild beauty as well as historically significant monuments to see, meaning it is the perfect place to stay for a few days. After spending a day or two seeing the artistic and historical places in the city, travelers should dedicate some time to hiking and exploring the Cape Charles Natural Area Preserve and seeing some of the local wildlife. Finally, the Bay Haven Inn of Cape Charles gives tired explorers a restful and quiet place to lay their heads while getting a front-row seat in one of the community's old homes. Tourists shouldn't worry; despite dating back to 1906, the inn is well-maintained and beautiful.
Maryland and Virginia rest within the region known as the Chesapeake Bay. These states have many unknown or lesser-known towns dotting their borders that provide awesome access to the bay's shorelines, all while giving guests a spectacular immersive experience within the watery region. The laid-back atmosphere of these small communities is perfect for those seeking to escape to the natural world and away from the hassles of life.
The bay areas are fantastic for explorers, whether they prefer sailing on a ship, fishing on the docks, or hiking in the marshlands. The Chesapeake Bay is an essential piece of the United States' food supply and wildlife preserve areas. But it's also the idyllic spot for environment-loving tourists to spend a romantic or adventurous weekend.
