"the Boulevard" as it became widely known locally, was a major factor in the growth of the Oceanfront town and adjacent portions of the former Princess Anne County (consolidated with Virginia Beach in 1963) as automobiles replaced streetcars and trains as a preferred mode of travel.

In the late 1950s, a former airfield near the intersection with Norfolk's semi-circumferential Military Highway became the site of JANAF, the largest shopping center in the eastern United States at the time.

Prior to the late 19th century, the Atlantic Ocean frontage of Princess Anne County from Cape Henry south to North Carolina was isolated, subject to severe weather, and largely uninhabited.

A line parallel to the beach extended north to Cape Henry, and Pullman car service was offered to the original landmark brick Cavalier Hotel, which attracted many affluent tourists.

In the early 20th century, rubber-tired motor vehicles emerged as preferred mode of travel for Americans, offering more personalized transportation for vacationers.