SR 149 begins in the Princess Anne section of Virginia Beach, which contains the city offices and courthouse, a vestige of when the community was the county seat of Princess Anne County.
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Militia companies from Princess Anne County in the Province of Virginia assembled at Kemp's Landing to counter British troops under the command of Virginia's last colonial governor, John Murray, Lord Dunmore, that had landed at nearby Great Bridge.
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Kemp's Landing incorporated in 1778 as Kempsville, and became the county seat for Princess Anne County.
The Little Creek Ferry operated between the Eastern Shore and Princess Anne County and transported vehicles as part of U.S. Route 13 and the Ocean Highway.
The school is named after the now extinct Princess Anne County, Virginia (itself named after the British Royal, Queen Anne, titled at the time and prior to ascension, Princess of Denmark) which was annexed with the founding of Virginia Beach.