Orange Riots at 25th Street and Eighth Avenue, 1871. Following violence the year before uptown on July 12th, (known as Marching Day in Northern Ireland), in 1871 the police barred the Loyal Order of Orange (an Irish Protestant group) from parading again. After complaints were lodged by newspaper, the order itself, and a number of elite businessmen, the police and Tammany Hall relented and allowed the parade. The event began under heavy police and National Guard presence (about 5000 men) at Lamartine Hall, the Orangemen’s headquarters at Eighth Avenue and 29th Street. The parade was met by angry Irish Catholic crowds and the violence escalated to the point that rocks, shoes, and bottles were being thrown; the police and militia were using their clubs and bayonets; and shots were fired into the dense crowds. In all the riot caused the deaths of over 60 civilians – mostly Irish laborers – and three Guardsmen.

Although it is often forgotten, Chelsea played a significant role in New York's African American community and its history, particularly in the second half of the 19th Century. As early as the 1840’s Pierre Toussaint a freed Haitian slave, now in the process of canonization, played a significant role in establishing St Vincent DePauls Roman Catholic on W 23 St for French speaking New Yorkers. This Church started an early school for African Americans in the city. On Lamartine Place, the block of West 29th St between 8th and 9th Aves, the Hopper-Gibbons a Quaker family that played a crucial role in Abolitionism and many progressive and charitable causes, used their house as a stop in the Underground Railroad. The house, still stands is to date the only verifiable Underground Railroad safe House in Manhattan. Particularly from the 1880s to 1900's (and lingering onto WWI), New York's African American community having been displaced from southern Greenwich Village settled in the West 20s and 30s. Thus the areas “Negro Tenderloin” was to the citys largest African-American settlement by the 1890s until once again the community was forced to move because of a brutal race riot in 1900 and displacement due to the demolition of a core area to build Penn Station. Faced with the prospects of bad living conditions, a violent and dangerous environment and displacement, St. Philips Episcopal Church, the city's oldest African American congregation which at the time was located on West 25th St played a central role in fomenting the move to Harlem by a significant portion of the cities African population. Several other of the cities older and most prominent black churches and institutions were in the neighborhood in the latter 19th Century including Bethel AME Church on W25 St and Mt Oliver and Shiloh on West 26th Street and the Colored Mission and the Sons of New York Club on West 30th St.

Bayard Rustin Residence at Penn South (Building 7), 312 West 25th Street. Bayard Rustin, one of the most important yet little-known figures of the civil rights movement, lived in an apartment in this Chelsea building complex from 1963 to 1987 (his death). While here, he served as the lead organizer of the 1963 March on Washington for Jobs and Freedom and took part in numerous social justice campaigns around the world.

Grand Opera House, 1937. Originally opened as Pike's Opera House in 1868, the building became the Grand Opera House the next year when it was purchased by James Fisk and Jay Gould. The repertoire was expanded beyond classic opera to include plays and light opera. Fisk's motivation for this was to create opportunity for his girlfriend, actress Josie Mansfield. He put her up in a nearby brownstone and gifted her cash and lavish jewels. The mansion also had a secret tunnel that led to the opera house and the upstairs offices of Fisk's Erie Railway. Fisk became the silent partner in an oil business run by a man named Ned Stokes. Stokes would became Mansfield's other lover and after much drama, including extortion, blackmail, libel lawsuits, and false charges of embezzlement, Stokes murdered Fisk, shooting him in 1872. Fisk lay in state at the opera house. The theatre became a venue for more popular, working class productions, as the changing audience on the west side enjoyed a cheaper and less cultured repertoire. The building became an RKO theatre in 1938 after a renovation by theatre architect Thomas Lamb. Finally closed in preparation for demolition in June of 1960, the building was gutted by a fire in July of the same year.