Winchester is a gorgeous historical town that is located in Northern Virginia, just north of Shenandoah Valley. You can explore historical landmarks, buildings that are centuries old, fantastic dining and quaint boutique shops.
2. St. Michaels
St. Michaels is a dream summer town that is full of marinas, seaside restaurants and charming shops. The seafood at St. Michaels is absolutely delicious and it’s a perfect place for a boat cruise around the bay.
Fredericksburg is another Virginia town that is perfect for a summer trip. It’s located right on the Rappahannock River so it’s great for nature lovers. And it is known for being a historical destination. You can explore the childhood home of George Washington and Civil War battlefields where history still lives on.
Berlin Maryland was named America’s Coolest Small Town in 2014. In addition to having one of the best Main Streets in the area, this is a community oriented town. There are plenty of summer events that visitors can enjoy.
Onacock is a town in Virginia that dates back to the 1600s. It’s just off the Chesapeake Bay making it a favorite of kayakers and boaters. Inland, the downtown streets come alive with fun restaurants, historic buildings and buzzing boutiques.
Urbanna is a port town in Virginia and it is a fantastic weekend getaway. Take a ride on their trolley through town. Play in the two gorgeous public parks,. Shop at the farmers' markets or camp at the Bethpage Camp-Resort.
Leesburg is in Loudoun County, in Northern Virginia. Leesburg is set in the middle of rolling hills of wineries, Civil War battlefields and historic plantations. It's also close to the popular outlet mall.
Purcellville is a bustling town with plenty of exciting summer events. There are weekly farmers’s markets, the popular Wine and Food Festival and outdoor concerts. The 13-acre Fireman’s Field is also one of the most popular summer attractions.
Crisfield is the southernmost town in Maryland on the Eastern Shore of the Chesapeake Bay. With a history in the seafood industry, Crisfield has some of the best seafood in the entire area. Boating, kayaking and sailing are popular summertime activities in Crisfield.
Milton is a Delaware town with historic roots and a strong community spirit. It’s located on the Broadkill River, a few miles from the Delaware Bay. Visit Milton to find a hometown feeling. You can also enjoy great food, outdoor activities and fun events. Don't miss the annual Bargains on the Broadkill festival.
11. Solomons Island
Solomons is a cute waterfront village on the Patuxent River in Maryland. It was voted one of the 15 Happiest Seaside Towns in America. There are plenty of outdoor festivals, fun destinations and gorgeous nature. Explore the nearby Calvert Cliffs State Park, learn history at Calvert Marine Museum and stroll along the Riverwalk for gorgeous views.
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