Waterbury, Connecticut's first Puerto Rican Day Parade & Festival took place in 1969, Samuel Tirado Sr, of Guanica, Puerto Rico, and resident of Waterbury, was chosen by a representative committee to organize and stage the Connecticut Puerto Rican Day Parade and have it in the Brass City.

Later that year, Mr. Tirado Grand Marshaled the first Puerto Rican Day Parade in Waterbury. The idea was to have the annual parade hosted in distinct cities around Connecticut each year. Since then, multiple cities in Connecticut such as Hartford, Meriden, Bridgeport, New Haven, New Britain and Waterbury have had the opportunity to host their own individual Puerto Rican Day Parade/Festival every year.

The second and last time Waterbury had a Puerto Rican Day Parade was in 1999 when again the statewide Parade was to be held in the Brass City. Local firefighter Alex Calderon, who was the 1999 local parade coordinator, says that the 35th annual statewide parade was one of the best. He claims that this parade had more than 50,000 spectators and people participating in the parade from around the state.

The current Waterbury Puerto Rican Day Parade & Festival Movement is a grassroots initiative started by a new era of Greater Waterbury's Afro/LatinX individuals and the people of the City who want this cultural institution to return to the Brass City Summer 2023.