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Sixteenth Street Northwest is a prominent north-south thoroughfare in the northwest quadrant of Washington, D.C.

Part of Pierre L'Enfant's design for the city, 16th Street begins just north of the White House across Lafayette Park at H Street and continues due north in a straight line passing K Street, Meridian Hill Park, Rock Creek Park, and the Walter Reed Army Medical Center before crossing Eastern Avenue into Silver Spring, Maryland where it ends at Georgia Avenue. The Maryland portion of the street is designated Maryland State Highway 390. The entire street is 7½ miles (12 km) long. From K Street to the District line, 16th Street is part of the National Highway System.

The Washington meridian, a prime meridian once in use in the United States, follows 16th Street NW.

Early in the city's history, many foreign embassies located on 16th Street because of its proximity to the White House. Many religious denominations followed suit by building significant churches on the street to serve symbolically as embassies, thus earning the street the nickname "Church Row." These include Foundry Methodist (attended by President Clinton), First Baptist (attended by Presidents Truman and Carter), St. John's ("Church of the Presidents"), and All Souls Unitarian, as well as the Masonic Temple and Jewish Community Center. While most of the embassies have moved to Embassy Row and other parts of the city, most of the churches remain. The street's northern and central portions (and the Crestwood neighborhood, in particular) have for a half century been home to D.C. black elite. Featuring 80-90 year old Tudor mansions, it is the chosen neighborhood of accomplished African Americans residing in Washington, D.C., including city government officials.^{[citation needed]}

The street's width, as well as its prominence, bisection of the city, proximity to Rock Creek Park, and importance as a thoroughfare, has made it a natural dividing boundary for Washington neighborhoods. Thus, outside of the downtown area, no neighborhood in the city overlaps both sides of 16th Street; the neighborhoods that surround it have 16th as either their eastern or their western boundary.

A pair of similarly named streets, 16th Street Northeast and 16th Street Southeast, are 3 miles (5 km) away in the northeast and southeast quadrants of Washington. They are contiguous with each other and parallel to 16th Street NW.

In July 2005, just before Congress's summer recess, Texas Republican congressman Henry Bonilla quietly introduced resolution H.R. 3525 to rename 16th Street NW "Ronald Reagan Boulevard" in honor of the former president of the United States. Mayor Anthony A. Williams objected on the grounds that the proposal changes Pierre L'Enfant's 1791 design for the city and would have cost an estimated $1 million for new signs and maps. The plan was ultimately squashed by Rep. Tom Davis, chairman of the House Government Reform Committee, and a fellow Republican representing Washington's Virginia suburbs.^[1]