Located right in the swamplands of Virginia’s tidewater, 105 miles southeast of Richmond, this city of 204,470 is steeped in colonial heritage. It was at the forefront of the colonialists’ battle with the British at Great Bridge (where the Chesapeake Municipal Center is now located), during the Revolutionary War in December 1775. Eighteen years later, the construction of the Dismal Swamp Canal began; it is now the oldest artificial waterway still in operation in the country.

Later occupied by Union troops during the Civil War, the city bounced back with a buoyant economy largely due to its natural resources by the water. While the focus is more on industry than tourism, there are several points of interest worth a glance. Visitors can take a walk along the trails of Chesapeake Arboretum or do some local stargazing at the Chesapeake Planetarium. An interesting museum, it features a sky theater in a dome ceiling, complete with some fascinating special effects that bring to life the phenomena of our vast and fascinating solar system.

Located in an area known as Hampton Roads—the crossroads of four cities—Chesapeake also sits within the beltway of I-64 and is serviced by Norfolk Regional Airport. Chesapeake is also accessible by rail from Newport News, which is only 10 miles away.