1. Floyd, Virginia
A small town with a population of 450 people, Floyd is big on personality. It’s a one stoplight town that is filled with bluegrass music every Friday night. The Floyd Country Store hosts the Friday Night Jamboree where locals and visitors come to enjoy the music and the fun.
2. Crisfield, Maryland
Crisfield is definitely the place of seafood lovers. In fact, it’s called the "Seafood Capital of the World." The town is home to a little over 2,000 residents and is kept busy by many tourists who visit throughout the year. It’s a great place to rent a boat and boat over to Tangier Island or enjoy an authentic clambake or crab feast.
3. Cape Charles, Virginia
Cape Charles is on the shores of the Chesapeake in Southern Virginia. Cape Charles has a little something for everyone. There are waterfront restaurants, charming cafes, old-fashioned soda fountains and so much more. You can shop at local shops, boat in marinas, golf at famous golf courses and learn about the history of the town at the Cape Charles Museum.
4. Hampstead Maryland
Over 6,000 people call Hampstead, in Carroll County, MD home. While it was once a farming hub, it has since grown into a bustling small town. You can enjoy nature at various parks or the nearby Cascade Lake. Or visit their downtown area and stroll by local cafes, restaurants and shops.
5. Thurmont, Maryland
Thurmont is in Northern Maryland close to Pennsylvania and is home to a little over 6,000 residents. It has a charming historic downtown area and its motto is "The Gateway to the Mountains," due to its close proximity to nature. Thurmont is home to popular hiking places Cunningham Falls State Park and Catoctin Mountain Park. It’s also the host of the Catoctin Colorfest, an arts festival that attracts over 100,000 people.
6. Oakland, Maryland
Oakland is a former railroad town that features a historic and preserved B&O railroad station. Oakland is a great place to escape to nature or enjoy small town charm. They are home to a vibrant arts scene and has one of the first designated Maryland Main Street. It’s near a few miles from Deep Creek Lake and Swallow Falls State Park.
7. Gordonsville, Virginia
Gordonville has a rich historic past that plays into their present day charm. There are quaint shops and restaurants in their downtown area. You will definitely want to try the fried chicken there as they are known as "the chicken-leg center of the universe." Every year they celebrate the "Gordonsville Famous Fried Chicken Festival." where you can enjoy history and delicious food, two staples of the town.
8. Onancock VA
It’s been said that Onancock is "the Gem of the Eastern Shore." Onancock is extremely walkable. They have an incredible arts scene, live theater, music, galleries and so much more. Outside of their downtown area, there is true natural beauty, along the creek that leads to the Chesapeake Bay.
9. Town Orange, Virginia
The Town of Orange is an old-fashioned small town. They have a historic downtown filled with shops, restaurants and historic sites. The businesses surround the Historic Orange Train Station, which was built in 1909. The 19th century County Courthouse and the James Madison Museum are two other popular attractions.
10. Leonardtown, Maryland
Leonardtown is a historic town with a population of almost 4,000 people. It might be best known for the national oyster-shucking championship it holds every year. But it has much more to offer than their annual event. They have recently revitalized their quaint downtown area and have beautiful waterfront views and activities along the Wharf.
11. Emmitsburg, Maryland
Emmitsburg is a college town as it’s the location of the historic Mount St. Mary’s University. It’s also a popular destination for Catholics as it is home to the National Shrine Grotto of Our Lady of Lourdes and the Basilica and National Shrine of St. Elizabeth Ann Seton. Situated in gorgeous countryside, it’s worth the drive for the views and the beautiful historic buildings!
12. Warrenton, Virginia
Warrenton has something for everyone! You can explore their historic downtown area and purchase unique items fro local artisans. Or hike, bike or walk along the local trails to Civil War battlefields. Located right in Virginia wine country, Warrantor is also home to fantastic wineries.
13. Washington, Virginia
Sometimes called "Little Washington," Washington is a gorgeous town in the foothills of the Blue Ridge Mountains in Virginia. It is best known as the location for the highly rated Inn at Little Washington Restaurant and Inn. The town still has the same five-block by two-block it did when George Washington first surveyed it in the 1700s. But today, those blocks are filled with galleries, theaters, shops and restaurants.
14. Occoquan, Virginia
Occoquan in Prince William County has a population of 1,000 people. It’s seated on the banks of the Occoquan River and is rich with history and personality. The town was home to America’s first automated grist mill. Today, the streets are lined with unique boutiques and fantastic restaurants. You can also enjoy water activities on the water.
15. Middleburg, Virginia
Middleburg is the nation’s Horse and Hunt Capital and was established in 1787. It’s a well-known destination for equestrian events. It’s also one of the top 10 wine destinations in the world. In between horses and wine, Middleburg features beautiful rolling hills and gorgeous landscapes.