Virginia Beach Boulevard

Virginia Beach Boulevard is a major connector highway which carries U.S. Route 58 most of its length and extends from the downtown area of Norfolk to the Oceanfront area of Virginia Beach, passing through the newly-developed New Urbanist Town Center development of the latter as it links the two independent cities in the South Hampton Roads subregion of the Hampton Roads region in southeastern Virginia.

The first hard-surfaced road from Norfolk to Virginia Beach, Virginia Beach Boulevard opened in July 1921. "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 time. When indoor shopping malls became the newest trend a few laters later, Military Circle Mall was built in another quadrant of this major intersection. As traffic continued to grow, Virginia Beach Boulevard was largely paralleled by the Virginia Beach Expressway, a toll road which was completed in 1967. Originally designated Virginia State Route 44, after the toll revenue bonds were retired, it became toll-free and was re-designated as part of Interstate 264. However, "the Boulevard" continues to serve in many ways as Virginia Beach's equivalent of "Main Street" in the early 21st century.