After inheriting some land in the Shenandoah Valley in 1780, George Washington's younger brother Charles moved to the area to build his home, which he named "Happy Retreat." In 1786, he petitioned the General Assembly to create a town. He named the streets in the new town for his brothers and his wife and named it "Charles Town." The town square is named for his much-more-famous older brother, George. When Jefferson County was formed in 1801, Charles Town became the county seat.

The remarkable history of Charles Town is on full display at the Jefferson County Museum, but it is also in the Downtown Historic District -- a fantastic collection of historic buildings containing a wide variety of shops and restaurants. Charles Washington's home, Happy Retreat, still stands along Mordington Avenue. The 12-acre property surrounding the house is often used for events, such as the popular Craft Beer & Music Festival and the Charles Town Heritage Festival.

While the town's history and beautiful downtown attracts visitors, Charles Town is also home to the Hollywood Casino at Charles Town Races, which features the casino, an event center, and thoroughbred horse racing. When Charles Town residents want to explore the culture and history of the city named for Charles' famous brother, Washington, DC is just an hour southeast.