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The area is steeped in 400 years of American history, and hundreds of historical sites and attractions in the area draw visitors from around the world each year. The harbor was the key to the Hampton Roads area's growth, both on land and in water-related activities and events. Ironically, the harbor and its tributary waterways were (and still are) both important transportation conduits and obstacles to other land-based commerce and travel. Creating and maintaining adequate infrastructure has long been a major challenge. The Hampton Roads Bridge-Tunnel (HRBT) and the Monitor-Merrimac Memorial Bridge-Tunnel (MMBT) are major harbor crossings of the Hampton Roads Beltway which links each of the largest Seven Cities of Hampton Roads. In 2007, the new Hampton Roads Transportation Authority (HRTA) was formed under a controversial state law to levy various additional taxes to generate funding for major regional transportation projects, including a long-sought and costly third crossing of the harbor of Hampton Roads, which claims to be "America's First Region."

The word "Hampton" honors one of the founders of the Virginia Company of London and a great supporter of the colonization of Virginia, Henry Wriothesley, 3rd Earl of Southampton. In the easternmost part of the new colony, downstream from Jamestown, the early administrative center was known as Elizabeth Cittie [sic], named for Princess Elizabeth, the daughter of King James I, and formally designated by the Virginia Company in 1619. (The Elizabeth River was also named for the princess).The town at the center of Elizabeth Cittie became known as simply "Hampton", and a nearby waterway was designated Hampton Creek (also known as Hampton River). The town (and later city) of Hampton was the county seat of Elizabeth City County for over 300 years, until they were politically consolidated into the current large independent city known as Hampton, Virginia in 1952. The City of Hampton thus became one of the large Seven Cities of Hampton Roads, of which four others also grew to the larger sizes by consolidating with neighboring jurisdictions such as counties and towns in the mid-twentieth century.