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Chesapeake City, MD - The charming small town located at the northern end of the Chesapeake Bay, is known for its unique views of ocean-going vessels. Crossing the Chesapeake Bay Bridge from Annapolis to Maryland's Eastern Shore, one is abruptly transported to a rural countryside serrated by scores of coves and inlets and dotted with a charming collection of small towns. By the mid-1800s, many ship companies wanted a piece of the Chesapeake pie and competed for customers by promising hard-to-resist amenities and attractions. World-class museums, thriving arts and culture districts, history, nightlife, music and more make Baltimore the urban jewel of the Chesapeake Bay. Heading down to the towns along Virginia’s Northern Neck and Middle Peninsula seems to be on more of my readers’ radar now that we’re turning to drive-able destinations for our summer trips. Photograph by Loblolly. Whether a small cottage along a creek minutes from the Rapphannock River for weekend getaways or a magnificent mansion with expansive views of the Bay, living on the water is special. Start Slideshow 1 of 10 Steamboats were also built for fun. The historic area sits just south of the Chesapeake & Delaware Canal, a 14-mile canal that dates back to 1829. The Chesapeake Bay watershed includes parts of six states (Virginia, Maryland, Delaware, West Virginia, Pennsylvania and New York.) We’ve visited other small towns in the South, Berlin, Maryland Tangier Island, Virginia Beaufort, North Carolina Charles City, Virginia 16 Great Small Towns … Local tip: Start the day with the “famous French toast” at Cape Charles Coffee House (241 Mason Ave.; 757-331-1880), in a 1910 former bank with Art Deco chandeliers. And water-loving retirees still have access to the same torrent of activities, such as kayaking, canoeing, boating and fishing, common on the Chesapeake Bay. Chesapeake Bay towns are in either MD or VA, and for both there's an eastern shore or a western shore of the Bay.Both of those states also have ocean resorts, farther south than the DE ocean beaches. Local towns near Chesapeake, VA. With a half dozen busy galleries and a respected fine-arts museum, little Easton regularly gets named one of the best small towns for art in America. Not a square inch of Delaware is on the Chesapeake Bay.. Do you want ocean or bay? Easton Maryland, named one of the Best Small Towns in America, is nestled on the eastern shore of beautiful Chesapeake Bay. Shops and restaurants line the main drag, Mason Avenue, which ends at one of the nicer beaches on the bay. Nicknamed a “Nest of Pirates” by the British, the people of Fells Point prefer the term “Privateers.” The Maryland Eastern Shore, a peninsula extending hundreds of miles between the Chesapeake Bay and the Atlantic Ocean, offers endless recreational opportunities and is a popular summer vacation destination. With 12 marinas, a yacht club, and a custom sailmaker in town, it’s truly a boaters’ paradise. The Chesapeake Bay, located on the eastern edge of Virginia, is a body of water over 200 miles long which creates over 11,000 miles of shorelines between the actual bay and its tributaries. If you're planning a road trip or exploring the local area, make sure you check out some of these places to get a feel for the surrounding community. Upper Bay/Maryland’s Upper and Mid–Eastern Shore Crow Farmstay B&B. Academy Art Museum. HdG Among Top 10 Small Towns On Chesapeake Bay - Havre de Grace, MD - One of the top 10 small towns on the Chesapeake Bay is Havre de Grace, a magazine reports. ... on the Eastern Shore of the Chesapeake Bay—increases its appeal and … Floating theaters delivered entertainment to arts-starved small towns, while moonlight dance cruises brought music to sleepy harbors. This is a list of smaller local towns that surround Chesapeake, VA. Chesapeake City

Like many cities on the Chesapeake, Rock Hall began as a sleepy harbor town; what’s unique is how much this town on the upper Eastern Shore has maintained that salty spirit. Maryland's Chesapeake Bay offers quaint and memorable small towns, fresh-from-the-sea crab, and lots of laid-back leisure. Hi, "Seaside towns" in DE are ocean towns. We’re skipping the popular vacation spots in the area, such as Williamsburg, Jamestown, and the adventure parks, and instead opting to visit the lesser known regions further north along the Chesapeake Bay. Travel Recommendations for Virginia’s Chesapeake Bay Towns. From coast to coast, these towns have it all: affordability, nature, entertainment, and a sense of community. You can also search for cities 1 hour from Chesapeake, VA (or 2 hours or 3 hours).