U.S. Route 29 (US 29) enters Washington, D.C., via the Key Bridge from Arlington County, Virginia, and exits at Silver Spring, Maryland.

[citation needed] Before the Whitehurst Freeway was built, the Georgetown waterfront experienced periods of prosperity and decline.

The Whitehurst Freeway would form part of the innermost loop, which was an ellipse roughly centered on and built about one mile (1.6 km) from the White House.

)[5] Planning for a "sky-road" above K Street Northwest along the Georgetown waterfront was already long-planned by the time architectural drawings were released to the public in December 1941.

[10] Gas rationing during the war caused the number of automobiles on roads to drop precipitously, helping to make the freeway unnecessary.

In May 1943, the U.S. Commission of Fine Arts approved a plan for postwar construction in Washington that gave a high priority to the K Street freeway in fiscal 1947 (which began in July 1946).

[14] The Des Moines, Iowa, firm of Alexander & Repass successfully bid to construct the viaduct.

The report urged the city to bury the freeway in an enclosed trench and sell the air rights above it to developers or use it as parkland.

[22] But in 1977, DC director of municipal planning Ben Gilbert claimed that the Whitehurst Freeway's "removal is not practical in the near future and maybe never".

Prior to the rehabilitation, city officials studied the feasibility and cost of either burying the freeway in a tunnel or widening K Street Northwest into a much larger boulevard.

[24] In 2007, DC Mayor Adrian Fenty halted plans for an environmental impact study for the proposed demolition, stating that his administration is "not going to be spending money on this particular issue.