8 of the Most Welcoming Towns on the Chesapeake Bay
The Chesapeake Bay on the Atlantic Coast is the largest estuary in the United States and the third largest in the world. It is home to over 18 million people and 3,600 plant and animal species, and its shores encompass six states plus Washington, D.C.
There is a cozy blend of small towns and large cities that surround the bay. Most of the small towns have rich histories and welcome visitors to come and discover what makes these coastal towns so special. The following six towns are especially friendly and have a lot of coastal charm to offer visitors.
St. Michael's
Saint Michael's, in Talbot County, Maryland, has a population of less than 2,000 people. The quaint historic town dates back to the 17th century when it was a trading post for tobacco farmers and trappers. In 1778, James Braddock deeded 58 lots from his 20 acres which culminated in the historic St. Mary's Square, now home to St. Michaels Museum.
Although considered a posh town that centers around the marina, St. Michael's has a small town atmosphere and friendliness. Several museums highlight the history of the town and the Chesapeake Bay and historic home tours introduce visitors to the significance these homes have had on the community. Saint Michael's is a hip, friendly, and historic town that offers visitors the best of the coastal lifestyle while embracing its past.
Chesapeake City
Chesapeake City in Maryland is on the National and Maryland Historic Registries due to the restored homes and historic buildings downtown. Don't let the word city in the name fool you though, this is a small seaside community has a population of less than 1,000 people. Originally named Bohemia Manor, the town still embraces the bohemian atmosphere that makes these coastal towns so unique.
The waterfront shopping and dining scene is an eclectic blend of modern retail and antiques as can be seen at Belle on Bohemia. The dining ranges from casual to sophisticated and all the restaurants have a waterfront view with the Chesapeake City Bridge providing a romantic backdrop. The town is open to guests and visitors to explore the Victorian architecture, quiet waterfront dining, and an inviting atmosphere.
Cambridge
Historic Cambridge, Maryland, established in 1684, is one of the oldest Colonial towns in the nation. Being located on the banks of the Choptank River and the Chesapeake Bay, the coastal town has a rich maritime heritage including boat building and commercial fishing. This vital history is celebrated at the Richardson Maritime Museum and the Ruark Boatworks, which has daily tours.
Cambridge is known for its Victorian architecture and, starting in 1986, a group of citizens started efforts to preserve the architectural heritage. Walking tours are available and this is the perfect way to see Cambridge in all its glory. The walking tour leads visitors to the historic downtown with brick storefronts. Downtown has been recognized as a national and state level "Main Street District" and is filled with galleries, museums, and local shops in historic buildings.
Oxford
Oxford is a true waterfront town in Talbot County Maryland with historic buildings, a maritime legacy, and a small town atmosphere that welcomes visitors. One of Maryland's oldest towns, Oxford is on the National Registry of Historic Places, and historic homes, picket fences, and a cozy atmosphere set the scene in this historic town. It also boasts the nation's oldest ferry routes, an ideal way to view the Chesapeake Bay.
The Robert Morris Inn which was established in 1710 is the oldest full service inn in the nation and a great way to capture the history of this storied town. The restaurants here are incredibly varied for such a small town and have put Oxford on the culinary map. There are also museums like The Oxford Museum that showcase the charming history of this small yet thriving community.
Easton
Easton, Maryland is a Main Street town and is known for its historic downtown and laid back atmosphere. The quaint downtown is mostly brick storefronts and historic buildings and there are daily walking tours available to discover the history of this coastal town, including ghost tours. To add to the charm, downtown also has an array of Victorian bed and breakfasts, live theatre shows at The Avalon, and a pub crawl for the adventurous visitor.
Only 70 miles from Washington D.C., many folks come here to unwind and take in one of the many restaurants that range from casual to five star cuisine. The history also is a big draw for many. In 2011, the people erected a statue of Frederick Douglass, who was born here, and it is a popular stop along the guided walking tours. The atmosphere feels different than other towns and the coastal charm is infectious.
Crisfield
Crisfield, one of the youngest towns on the Chesapeake Bay at only about 160 years old, was once known as the "seafood capital of the world". There are walking tours and carriage rides through historic downtown and the Tangier Island Cruises offers boat excursions through Tangier Sound from May until October.
The Tawes Museum, operated by the Crisfield Heritage Foundation, is where you can go to learn about the maritime and cultural history of this port town. The historic district contains homes, commercial buildings, and churches primarily from 1870-1930 and reflects the economic growth of the oyster boom from that period. Crisfield is on the National Register of Historic Places and is a tight knit community that is welcome to visitors.
Havre de Grace
Havre de Grace is at the head of the Chesapeake Bay and is named after the coastal city of Le Havre, France. This historic town is known for its waterfront views, quaint downtown, and historic homes. The town is proud of its history and there are several museums and a visitor's center that highlights the local history.
The best way to explore Havre de Grace is on foot. A stroll through the historic downtown continues along the Bayfront boardwalk to the Concord Point Lighthouse. The town also has a dozen parks to visit and is known for its walking trails and natural beauty with some crowning it as the "jewel of the Chesapeake Bay". Havre de Grace is a welcoming spot for seafood lovers, outdoor enthusiasts, and history buffs.
Annapolis
Annapolis is famously known as the home of the US Naval Academy, but it is also a welcoming and historic town for visitors to explore. The historic downtown is reminiscent of the 19th century with brick architecture dominating the commercial buildings and houses. There is also the domed 1700s Maryland State House and a Romanesque Anglican church with a historic cemetery.
Annapolis has been voted one of America's prettiest and most walkable cities time and again. Start the day on Main Street and soak in the history and the views and it is clear why the town tops the list. There are shopping and dining opportunities along the walking route but also historic homes like the Hammond-Harwood House and the William Paca House and Gardens. And, of course, the walking tour winds by the historic US Naval Academy. This is a beautiful town that openly receives visitors from around the world and should be on any visitor's list of places to see on the Chesapeake Bay.
The Chesapeake Bay is a beautiful and historic body of water on the Atlantic Coast. The welcoming towns are easily walkable and each one has a rich history. From historic port towns to commercial fishing villages, the people who are the fabric of these communities love to share their history with guests. When one visits the Bay, one gets a sense of community and pride that has helped these towns endure the test of time, moving into the future while preserving their historic roots.
