In the 17th Century, the South Village belonged to a single property owner, Wouter Van Twiller, who was appointed by the Dutch West India Co. in 1633 as Director General of the colony. Van Twiller took this whole area as his personal farm. Van Twiller's successor, William Kleft, granted ownership to a Symon Congo, making Mr. Congo one of the first black landowners in the new colonies. Ironically, two hundred years later in the mid-19th Century this area around Bleeker, Sullivan and MacDougal was known as "Little Africa" because by 1865, one quarter of New York City's black population lived there. The first African American newspaper and the first African American Theatre, "The African Grove" was located here on Mercer Street.

The most famous resident of this area was George Washington who, in 1776 set up his headquarters in the mansion known as Richmond Hill. This site between Charlton and King Street west to Vandam, was also used by John Adams, when he was Vice President. Later, Aaron Burr used Richmond Hill for his social gatherings where Jefferson, Madison and Talleyrand would congregate. Finally, in 1817 John Jacob Astor purchased it and subdivided it into smaller lots. Authors Edna St. Vincent Millay (25 Charlton Street in 1918) and James Agee (17 King Street in 1951) lived here.

This area continually attracted rebels from George Washington to John Reed and his buddies at the Liberal Club, also known as Polly'sRestaurant, at 137 MacDougal Street. This group included Theodore Dreiser, Upton Sinclair, Sinclair Lewis, Lincoln Steffens, Max Eastman and others. Eugene O'Neill was there but preferred The Golden Swan, known as the Hell Hole and based his play "The Iceman Cometh" on his friends at this Village hangout. Later this group of writers, artists and intellectuals formed the Provincetown Playhouse to showcase their work. The most famous Greenwich Village restauranteur of the 20th Century was Romany-Marie. Her restaurant at 133 Washington Place was frequented by all of the Village's most illustrious characters. Buckminster Fuller decorated the restaurant in payment for his daily lunch. Marilyn Weigner Associates has one of the last surviving portraits of Romany in their Greenwich Village collection.

This neighborhood has always been known for its eclectic mix of cafes, bars, theatres restaurants and jazz clubs. Bob Dylan showcased his talents on Bleeker Street, as did many of his folk singing generation. Many of these clubs still remain, including the Bottom Line, the Village Vanguard and the Blue Note; but lost is the Village Gate and many others.

Today this neighborhood is still a vibrant mix of café's, clubs and restaurants, making this truly the heart of Greenwich Village.