2024's 9 Most Adorable Small Towns in Chesapeake Bay
In the Mid-Atlantic region, the Chesapeake Bay is the largest estuary in the United States. It stretches between Virginia and Maryland and is a major shipping and transportation hub. Many historic towns along the bay, including the oldest European settlement, Jamestown, Virginia, established in 1607, are located there.
The small towns that inhabit the Chesapeake Bay coast are great destinations because of their easy walkability, historic architecture, and attractions. The townspeople are warm and inviting, and many community events occur in the town squares. The beaches and lighthouses are popular among those looking for a tranquil time. Here are the nine most adorable small towns in Chesapeake Bay.
Cape Charles, Virginia
Cape Charles, Virginia, is a small coastal town bordered by the Chesapeake Bay to the west, King's Creek to the north, and Old Plantation Creek to the south. Though it has a small population, there is much to see and do. Driving into town has its own adventure as most visitors drive through the 17.6-mile Chesapeake Bay Tunnel. Other points of interest include Cape Charles Museum, Kiptopeke State Park, and Eastern Shore of Virginia National Wildlife Refuge.
The brick museum started as a generator station and continued as a public work building into the 1980s. It explores the town's history and the historic railway tracks behind the building, which are still operational. Kiptopeke has access to the Chesapeake Bay, along with cabins and primitive camping, and the refuge is one of America's most important layovers for migratory birds. This adorable town has many more natural and cultural attractions and is one of the best on the bay.
Irvington, Virginia
Irvington, Virginia, is a beautiful small town bordered by the Rappahannock River and the Chesapeake Bay. It is known for its fresh seafood, vineyards, and cultural points of interest. The Steamboat Era Museum celebrates the region's maritime history with dioramas, exhibits, and a restored pilothouse from the tug, "Potomac." Oenophiles can cover a seafood dinner and a vineyard tour at the Hope and Glory Inn and Oyster House at one time. It is a gorgeous inn with luxury accommodations and fine dining on the Dog and Oyster Vineyard.
Dredge is a quaint restaurant that serves steamed clams and fried oyster tacos, perfect for lunch while exploring Irvington. A notable inn is The Blue House, built in 1890. It offers waterfront views and charming rooms and is a short walk or bicycle ride from the town center. Irvington has one of the world's largest Cape Dory Typhoon fleets, and visitors are welcome to walk the docks to experience this unique heritage.
Onancock, Virginia
The adorable Onancock, Virginia, was an important steamboat layover in the 19th century. Steamboats from Baltimore, Maryland, and Norfolk, Virginia, because of its proximity to the Chesapeake Bay and Onancock Creek. The town also has a bustling downtown area with award-winning restaurants, live theater, and community events.
The 1882 Colonial Manor Inn is a notable point of interest and today serves as a bed and breakfast. The Inn at Onancock and the Charlotte Hotel are also historic inns downtown, where everything is just a short walk from the inns. Onancock is a serene setting with a pleasant atmosphere, and staying at one of the historic inns gives visitors a real sense of the town's lineage.
Yorktown, Virginia
In 1781, George Washington's Army defeated the British during the battle of Yorktown, Virginia. The American Revolution Museum explains this battle and other events, including the birth of the United States. Period actors act out live reenactments of a Continental Army encampment with demonstrations on medical treatment, cooking, and other activities. Other cultural attractions are downtown art galleries, like the Gallery at York Hall.
The Riverwalk Landing is a popular downtown gathering spot that hosts concert series like Sounds of Summer and Rhythms on the Riverwalk. Restaurants range from coffee shops to cafes to fine dining. Riverwalk Restaurant on Water Street serves delicious seafood, steak, and burgers. Downtown also has historic inns within walking distance of the Riverwalk, shops, and restaurants.
Havre de Grace, Maryland
Havre de Grace is a popular destination in Maryland because of its architecture, history, and abundant cultural and natural attractions. It is also home to the Concord Point Lighthouse, the second oldest in Maryland. Several walking tours are available, including the City Tree Walk and the Havre de Grace Walk.
The lively downtown boasts attractions like the Havre de Grace Maritime Museum and the Susquehanna Museum at the Lock House. A walk downtown Main Street leads visitors past vintage brick facades and trendy dining options from seafood to Cajun fare. The town is also known for its parks and trails, like Concord Point and David Craig Park. The public art displays add a pleasant aesthetic to the downtown areas and parks, making Havre de Grace irresistible.
Oxford, Maryland
The charming town of Oxford is a quaint waterfront village in Maryland and one of the oldest towns in the US. Downtown, there is a Town Clock, classic brick facades, and the Oxford Museum. The museum is in a 19th-century structure and showcases that highlight the local heritage with exhibits and demonstrations. There are also historic bed and breakfasts throughout town, each telling part of the town's story.
The Elizabethan-era Robert Morris Inn was established in 1710 and is the oldest full-service inn in the nation. It is named after one of the original signers of the Declaration of Independence, and it was his childhood home. The most picturesque way to enjoy the town is by boarding the Oxford-Bellevue Ferry. It started its journey in 1683 and is the oldest ferry in the US. The historical significance of Oxford is undeniable, and it is one of the best towns on the Chesapeake Bay.
Annapolis, Maryland
Annapolis, the capital of Maryland, is home to the United States Naval Academy and is known as the "sailing capital of the US." The historic district comprises 18th—and 19th-century structures, including a Romanesque Episcopal church and the beautiful domed Maryland State House, constructed in 1772 and the oldest in use today. It was the nation's original capital, and the Treaty of Paris, which ended the Revolutionary War, was signed in its hallowed halls. The downtown area is often considered one of America's best for its colorful charm and historic buildings.
The Banneker-Douglass Museum is Maryland's official African American museum, focusing on Benjamin Banneker and Frederick Douglass. No visit to Annapolis is complete without a tour of the prestigious Naval Academy, which has trained naval officers since 1845. Along with the Academy Museum, the domed chapel is said to hold the crypt of John Paul Jones, the founder of the US Navy. Annapolis also has modern conveniences like the Annapolis Town Center, a diverse collection of shops, restaurants, and live entertainment.
St. Michaels, Maryland
St. Michaels, Maryland, is an important seaport that has maintained its heritage and nautical aesthetic. The town's history is explored at the Chesapeake Bay Maritime Museum, an 18-acre property that includes the 1879 Hooper Strait Lighthouse, a working shipyard, and live exhibits. There are also non-maritime museums like the Classic Motor Museum, which contains a rotating stable of classic automobiles and tractors.
The charming downtown is filled with boutiques and antique shops, which is one of the main reasons so many visit. The St. Michaels Museum at St. Mary's Square, built in 1964, interprets St. Michael's history and its impact on the town. Downtown also has several waterfront restaurants like The Fool's Lantern. It is the first self-serve wine and taproom and has a great menu. St. Michael's is one of the best towns on the Chesapeake Bay because of its history, atmosphere, and cultural points of interest.
Cambridge, Maryland
Friendly and welcoming Cambridge, Maryland, is one of the oldest colonial settlements in the US. It also played a significant role in African American history, especially with the prominent figure Harriet Tubman. Growing up in the county, she suffered a head injury at the Buckman Store, which is believed to have led her to become a conductor on the Underground Railroad. The 125-mile Harriet Tubman Underground Scenic Byway traces pivotal stops along the underground tunnels that helped enslaved people gain their freedom.
Main Street is a small-town Americana with brick facades parallel to the Choptank River. It has a lot of personality, shops, and restaurants. The community hosts yearly live events, including the popular Groove City Culture Festival every Spring. There are several bed and breakfast options. The Cambridge House, Victoria Gardens, and Marvels on the Creek are historic inns within walking distance of the popular and historic attractions.
The Chesapeake Bay is a historic and beautiful estuary in the Mid-Atlantic region of the United States. It also has adorable coast towns and villages along the coastline with beautiful scenery and inviting downtown areas. Some of these towns, like Yorktown, Virginia, and Annapolis, Maryland, played pivotal roles during the American Revolutionary War.
Cambridge, Maryland, was the birthplace of the great Harriet Tubman, and the town honors her legacy today with a museum and several historical sites. There are also modern comforts and cultural attractions like the public works of art in Havre de Grace. Whether it is the historical value, shopping centers, or natural attractions, these are the ten most adorable towns on the Chesapeake Bay.
