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St. Michaels Harbor in historic Saint Michaels, Maryland

8 Darling Small Towns In Chesapeake Bay

The Chesapeake Bay is the largest estuary in the US and spans six states along the Atlantic Seaboard. It is also a transportation hub, with many commercial vessels plying the waterways and tributaries. The coastal towns along the bay's banks have a lot of character and are known for their history and lively atmosphere. Annapolis is a famous town home to the United States Naval Academy. The region also has many cultural interests, such as museums, theatres, and historical sites. The small towns are packed with entertainment and charming restaurants. Here are eight darling towns in the Chesapeake Bay.

Annapolis, Maryland

Aerial view of Annapolis, Maryland
Aerial view of Annapolis, Maryland.

The state capital of Annapolis, Maryland, is notable as the home of the United States Naval Academy. It is also known for its elegant architectural styles, like the academy's beaux-arts style. The historic district includes the 1700s Maryland State House and notable commercial buildings and homes. The small town also has many cultural attractions, like museums and elegant gardens.

The Annapolis Maritime Museum and Park explores the town's history and the ecological wonders of the Chesapeake Bay. Another stunning attraction is the William Paca House and Garden, a tremendous 5-part Georgian mansion built in the mid-18th century and is a National Historic Landmark. The themed garden is an array of native and heirloom plants,

Havre de Grace, Maryland

Nightfall at the Concord Point Lighthouse, Havre de Grace Maryland
Nightfall at the Concord Point Lighthouse, Havre de Grace, Maryland.

Havre de Grace is a picturesque town in Maryland with a vibrant downtown area. Main Street not only has restaurants and shops, but it also has sculptures and points of interest like the Harmer's Town Art Center. The art center features an art mural, classes, and workshops. There are many more points of interest in this charming coastal town.

The artistic side of Havre de Grace shines through around the downtown area with public murals and sculptures. Birds of the Chesapeake is a delightful collection of ten statues of Chesapeake Bay birds on top of pilings along the bay. The Green Street Mural is a painting on the side of a commercial structure depicting underwater scenes, accessible to the downtown. This darling town is full of wonder, arts and entertainment, and pedestrian-friendly.

St. Michaels, Maryland

 St. Michaels Harbor in historic Saint Michaels, Maryland
St. Michaels Harbor in historic Saint Michaels, Maryland.

St. Michaels is a traditional and historic coastal town in Maryland. The lively downtown area has weekly events at venues like the Classic Motor Museum, Bistro St. Michaels, and Foxy Harbor Grille. The St. Michaels Museum at St. Mary's Square exhibits local history from the 19th century and offers docent-guided tours throughout town. Unsurprisingly, there are charming lodging accommodations, too.

The Old Brick Inn is an elegant bed and breakfast that offers 20 themed rooms between four historic residences. The historic Victoriana Inn is also a Victorian Inn with expansive gardens and quaint accommodations. St. Michaels provides visitors with beautiful architecture, history, and small-town charm. It is one of the best towns on the Chesapeake Bay.

Cambridge, Maryland

Main Street in Cambridge, Maryland.
Main Street in Cambridge, Maryland. Editorial credit: 010110010101101 / Shutterstock.com.

The historic town of Cambridge, Maryland, was founded in 1684 on the banks of the Choptank River, making it one of the oldest settlements in the country. Part of its history revolves around the great Harriet Tubman. Historic sites include the Buckman Store, where she acted out in defiance as a small child, and the Harriet Tubman Underground Railroad Visitor Center. Cambridge has many other interesting sites, including the lighthouse.

The Choptank River Lighthouse is a replica completed in 2012. Admission is free, and self-guided tours are available. Other interests include the Visitors Center at Sailwinds, an excellent way to get to know the area before exploring the many sites. Top restaurants include RAR Brewing, which offers Maryland's "real ale" in the area in a microbrewery.

Oxford, Maryland

Boats in the harbor of Oxford, Maryland.
Boats in the harbor of Oxford, Maryland.

Historic Oxford, Maryland, is a tree-lined village that has retained its historic charm by not giving way to waterfront condominiums and commercial structures. The rich maritime history remains today, and it is not uncommon to see boatmen working on the boats in the mornings. Among the many historic sites is the Robert Morris Inn, the oldest full-service inn in the US.

The Ice Creamery, the Oxford Museum, and the Ferry offer maps for self-guided tours. The charming tour winds around white picket fences painted in various scenes by local artists, adding to the town's aesthetic. The Oxford Museum showcases over 300 years of Oxford's maritime and colonial history with artifacts and exhibits. The slower pace and vintage surroundings make this water town one of the best in the region.

Solomons, Maryland

Waterfront at Solomons Island, Maryland
Waterfront at Solomons Island, Maryland.

Solomons, Maryland, sometimes called Solomons Island, is the head of the Patuxent River and a boating hub. Visitors traveling by car will come over the 135-foot Governor Thomas Johnson Bridge, providing an excellent view of the coastal town. People interested in the town's maritime history should visit the Calvert Marine Museum, which offers exhibits and cruises down the Patuxent River.

The Chesapeake Bay Biological Lab, on the island's southern end, is another fascinating look into the bay's health and ecology. There are numerous bed and breakfast inns to complete a stay in Solomons. Solomons Victorian Inn is an elegant inn on the island's tip, and every room has harbor views.

Cape Charles, Virginia

Aerial View of Beach Homes in Cape Charles Virginia
Aerial view of beach homes in Cape Charles, Virginia.

Cape Charles is a scenic and historic town in Virginia bordered by King's and Old Plantation Creeks. This small village has many points of interest, including the Chesapeake Bay Tunnel. The 17.6-mile-long tunnel stretches across the mouth of the bay and makes for an exciting drive. The town also has several antique dealers, museums, and local shops.

The mission of the Cape Charles Museum and Welcome Center is to showcase the history of the eastern shore, primarily Cape Charles. Outdoor enthusiasts will love the Cape Charles Natural Area Preserve. The preserve, complete with a boardwalk, is considered internationally significant for migratory birds and features wetlands and bay views. Cape Charles has a pleasant mix of natural and cultural attractions, making it one of the best places to visit on the coast.

Onancock, Virginia

The marina in Onancock, Virginia.
The marina in Onancock, Virginia.

Onancock, Virginia, is a pleasant town with live theatre, an artistic vibe, and award-winning restaurants. The North Street Playhouse offers live performances yearly with three series and 12-15 shows per season. The diverse culinary scene does not disappoint at restaurants like Onancock Taphouse and the Terra Mare Restaurant in the Charlotte Hotel.

Cultural interests include the Historic Onancock School, which first opened its doors in 1921, and Ker Place. The home features period furniture, artifacts, and traveling exhibits. Onancock is filled with historical treasures and gorgeous restaurants that provide a respite after a day of exploring the region's deep history.

The majestic Chesapeake Bay is surrounded by darling towns that offer plenty of entertainment, historical sites, and cultural attractions. Annapolis, the state capital, is home to the US Naval Academy and has a walkable downtown area and charming decor. Towns like Havre de Grace are known for their architectural significance and elegant public art.

Art galleries are prominent in most of these coastal towns, adding to the natural ambiance of the surroundings. Most of the towns are in Maryland, but there are many quaint towns throughout the six-state region of the bay. These towns exude the best characteristics of the Chesapeake Bay, from the dining to the lodging options.

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