The Commonwealth's largest city (2000 population, 425,257), Virginia Beach was formed in 1963 from the merger of the then smaller city of Virginia Beach with the surrounding county of Princess Anne. What had been a summer resort strip along the Atlantic Ocean with farmland to the west has become a sprawling, year-round Edge City with its own recreational, residential, retail, military, and service sector nodes, but as yet no downtown to give it a truly urban identity. The southern half of the city, bordering North Carolina, remains agricultural.

The entries begin in the populous northern section of the city, move eastward to Cape Henry, then continue through the densely developed resort strip along the oceanfront, and terminate in the rural section to the south.