9 Of The Most Captivating Small Towns In Chesapeake Bay
When one thinks of the Chesapeake Bay, the largest estuary in America, thoughts of maritime history and fresh seafood may come to mind. While the bay is filled with both, it is also home to quintessential coastal towns that embrace the spirit of the region, unlike any other. Each one has something distinctive to offer, but they all share a commonality that ties them together.
This commonality comes from a love of the sea, the coastal life, and the area's history. These elements combine in these nine captivating towns that are warm and welcoming to visitors. Most of the villages are walkable, and this is the best way to experience what makes this region so captivating. After spending a day exploring the historic and other sites, there is no better way to finish the day than with a plate of fresh Chesapeake Bay seafood at a seaside restaurant.
Havre de Grace, Maryland
Charming and historic Havre de Grace on the banks of the Susquehanna River is a remarkable town with waterfront views, museums, and a quaint downtown district. Historic sites and museums abound here, and they are the best ways to learn about the coastal village's heritage and culture. A prime example includes the Concord Point Lighthouse and Keeper's House Museum.
The lighthouse was completed in 1827 and is the oldest publicly accessible lighthouse on Chesapeake Bay. The museum interprets the lighthouse's history through exhibits and artifacts. Another landmark heritage spot is the Havre de Grace Colored School Museum and Cultural Center, the first to offer high school education to African American students in Harvard County. Enjoy dinner at one of the fantastic restaurants, such as River City Crabs and Seafood, for an authentic coastal dining experience.
Cambridge, Maryland
Cambridge is one of the oldest colonial cities in the U.S., founded in 1684 along the banks of the Choptank River. As such, it is filled with maritime history and U.S. history centering around the Underground Railroad. The iconic Bucktown Store in Cambridge is where a young Tubman made her first public act of defiance, and any visitor should not overlook the historical site.
Touring the Underground Railroad Visitor Center brings this history to life, and the exhibits interpret its significance to the Civil War. The Spocott Mill is another historical landmark, featuring one of the last remaining post windmills in the world. The site also includes a one-room schoolhouse and blacksmith shop that give a glimpse of Cambridge's Colonial roots.
Oxford, Maryland
Founded in 1683, Oxford is one of the oldest cities in America. Today, it is a boating hub and a haven for artists. The historic district features several preserved landmarks, such as 216 Morris Street, where the longest-serving U.S. postmaster worked in the post office for 63 years. Another hallmark is the Grapevine House, which has been standing since 1785.
Antique lovers should head to the downtown area, where they will find unique treasures at numerous shops, including the Mystery Loves Company Booksellers. While shopping, make sure to visit the Scottish Highland Creamery, which has been voted "Best Ice Cream on the East Coast." The historic sites combined with modern amenities make Oxford one of the most captivating small cities in the region, and it offers something for everyone.
Chestertown, Maryland
Chestertown is a historic waterfront town known for its Colonial architecture and captivating arts scene on the banks of the Chester River. Founded in 1706, the historic college town features brick sidewalks and modern attractions; it is also pet-friendly, a significant draw for many. One of the best and most immersive ways to experience the village is aboard the schooner, Sultana.
The tall ship combines ecology with history in a fun-filled tour and hosts annual festivals like the Wooden Boat Festival, honoring the region's maritime history. Washington College is another landmark that should not be overlooked. Founded in 1782, it was the first college chartered in the sovereign U.S. It was named after George Washington, who served on the first board, and another captivating historical fact from this quaint maritime port of call.
Annapolis, Maryland
Annapolis, the state capital, is famous for being home to the United States Naval Academy, and almost every aspect of the town reflects this rich history. Its historic district contains 18th-century homes and the domes of 18th 18th-century Maryland State House. It is also a shopping mecca in the historic district. Along the brick sidewalks where some of the most famous men in American history once stepped, lie modern boutiques such as The Peake House and Evergreen Antiques.
The walkable area centers around Main Street, home to many restaurants and unique finds. The main drag leads to the City Dock, where you can relax and watch the many ships sail in and out of the harbor. Annapolis's history is astounding, and combined with its abundance of modern amenities, it makes it one of the best cities to visit on the bay.
St. Michaels, Maryland
Historic St. Michaels is on the Eastern Shore and known for its rich maritime history, charming attractions, and coastal atmosphere. To learn about this history, visit the Chesapeake Bay Maritime Museum, which aims to explore and preserve the environment and history of the entire region. Auto enthusiasts will enjoy the Classic Motor Museum, especially on Saturdays when the community meets up for its weekly "Cars and Coffee" show.
This is also the ideal destination for nightly libations with a coastal breeze. Breweries such as the Eastern Shore Brewing Company and others are popular for their craft beers and seasonal selections. There are also many fine restaurants to choose from, including Plates at 208. The fine dining establishment brings Mediterranean flavors to the savory flavors of the Eastern Shore for a meal you won't soon forget.
Cape Charles, Virginia
Scenic Cape Charles on Virginia's Eastern Shore is a dynamic town with several points of interest, including the Chesapeake Bay Bridge Tunnel, an underwater tunnel spanning an incredible 17.6 miles. Other interests include the Eastern Shore National Wildlife Refuge. The refuge is at the tip of the Delmarva Peninsula and part of a system of lands that protect the future of wildlife and its natural habitat. It is a great location to unwind and soak in the unspoiled nature of the Eastern Shore.
The Shanty is an excellent location to consider for lodging, enabling guests to soak in the whole coastal vibe of Cape Charles. The waterfront oyster restaurant is committed to sustainable practices by operating partners who appreciate the rarity of such a location. Before leaving, be sure to embark on a tour of the Invisible History of African Americans, 12 sites honoring the African American heritage of Cape Charles.
Onancock, Virginia
The historic port town of Onancock was settled in 1608 and today is a major draw for nature lovers and history buffs. Its unique history can be explored at the Ker House or the Watermen's Museum. The Georgian-style home, built between 1799 and 1803, has been restored to its former glory with period pieces and is now open to visitors. The museum explores and interprets the pivotal maritime and fishing industry that built the region's economic status, providing an ideal way to delve into what makes this region so unique.
Lodging at a bed and breakfast is the best way to experience this seaside village in all its charms. Options include The Inn, a Victorian masterpiece. The exquisite inn offers themed rooms and different packages that will make a stay at Onancock feel like home. Onancock is an alluring destination because it feels like stepping back in time, with a warm community and modern attractions, perfect for a peaceful retreat.
Irvington, Virginia
Irvington is a boater's paradise, and the community takes pride in its nautical background. This is evident at the enchanting Steamboat Era Museum that pays homage to the maritime traditions that made the region what it is today. The museum is next to the Commons, a popular shopping and cultural hub near the award-winning Farmer's Market.
No visit is complete without a stop at the Dog and Oyster Micro Vineyard. This celebrated winery has been a local favorite for over 15 years, excelling at pairing wines with the region's signature fresh oysters. Better yet, book a room at the Hope and Glory Inn on the same property for a truly magnificent stay in this unique coastal haven, within walking distance of some of the main attractions.
These nine towns are among the most captivating in the Chesapeake Bay. There are numerous reasons why, but each one resonates with the local area and offers preserved historical structures and modern amenities to those who stop in for a while. There is no shortage of things to do and see in this area, from coastal treasures to charming downtown districts.
The maritime and military presence is strong throughout the region, and this is apparent in Annapolis. The Naval hub also provides ample shopping opportunities, a unique combination that makes it one of the most charming towns in Maryland. History, seafood, and architectural buffs will be hard-pressed to find better sites anywhere. Chesapeake Bay has a singular charm that is hard to describe; it is best experienced, and these definitive towns should top any destination list!
