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During World War II, the military build-up meant more people locating in the South Hampton Roads area, and with people came automobiles, many of them. The military needed to move personnel and materials fast and could not be bogged down in traffic. Federal, state and officials of the independent city of Norfolk came up with a plan to build a more efficient highway to alleviate traffic problems. All parties agreed on a 15-mile (24 km) long semi-circumferential section, from the western edge of Norfolk County just outside of Portsmouth through a portion of Princess Anne County to reach Admiral Taussig Boulevard near the Norfolk Navy Base at Sewell's Point.
The proposed "super" highway, named Military Highway, was designed and built in 1943 for approximately $2.5 million. Military Highway can lay claim to a lot of "firsts." It was one of the first multi-lane highway (4-lanes, two in each direction) constructed in the area. The new roadway included several overpasses, bridges, interchanges and a roundabout called Lansdale Traffic Circle. The cloverleaf interchange constructed at Military Highway and Virginia Beach Boulevard was the first ever built in Virginia. Near the western end, there were 45 mph (72 km/h) S-curves as the highway passed on a bridge over the Virginian Railway, with short approach fills and considerable grades. The newly-created feature became known as Bower's Hill, although the area had that name much earlier, by the mid 19th century, according to old maps. As one of the highest features for miles around, Bower's Hill on the Military Highway became something of a landmark for travelers.
The Gilmerton Bridge, a new drawbridge, was built to cross the southern branch of the Elizabeth River, a location which provides access to port facilities and is a portion of the Atlantic Intracoastal Waterway. Military Highway also crosses the eastern branch on a fixed span bridge.
After World War II, businesses and residential development soared. In 1959, JANAF Shopping Center at the intersection of Virginia Beach Boulevard became the largest shopping center in Virginia for many years. As the area grew, Military Circle Mall (Norfolk's first indoor shopping mall in 1970), Best Square Shopping Center and other large developments soon located nearby. These brought thousands of additional people into the area to live, work and shop. With the influx of people came even more cars. The road was the site of the first Econo-Travel motel, which grew to become a major national motel chain.
Even with the new Interstate Highways in the area built beginning in the 1960s, by the 1980s, more than 50,000 vehicles traveled along Military Highway daily with 67,000 vehicles expected by the year 2010. The old "super" highway could no longer support the increased traffic volumes. The existing lanes were insufficient to handle the traffic and the bridges, especially the one at the Military Highway/Virginia Beach Boulevard cloverleaf, which had physically deteriorated to a point where restricting commercial vehicles, due to their weight, and reduction of speed was necessary. Reconstruction work began in 1985, and the busiest sections of the Military Highway, mostly a local thoroughfare, were modernized.