The first commemoration of Labor Day was held on Tuesday, September 5, 1882, in New York City, when a crowd estimated at 10,000 workers held a march. The holiday to mark the contributions of working men and women had been proposed by the Central Labor Union of New York.

A second Labor Day event was held the following year, and after that it was proposed to hold it every year on the first Monday of September.

New York's Central Labor Union urged organizations in other cities to hold similar events on the same day, and the idea spread. In 1885 labor holidays were marked in the industrial cities throughout America.

On Monday September 7, 1885, the St. Paul Daily Globe in Minnesota reported "In accordance with the preparations made by labor organizations and the proclamation of the mayor, a large number of the workingmen of St. Paul will indulge in a holiday today. A mammoth picnic will be held at White Bear, at which it is expected that fully two thousand people will be present from St. Paul, Minneapolis, and Stillwater and the day will be entirely devoted to pleasure."

That evening, the San Francisco Evening Bulletin published telegraphed dispatches detailing the activities held earlier in New York City and Chicago. According to the newspaper article, the 1885 New York "labor parade" contained nearly 30,000 marchers, with female typesetters, silk weavers, shirt-makers, and cigar-makers riding in omnibuses or carriages.

About 8,000 people gathered that day for the "labor demonstration" in Chicago. The newspaper report said American flags were displayed proudly alongside banners for the various trade organizations, along with some banners demanding an eight-hour work day and a ban on convict labor. The Chicago parade featured decorated wagons, some of them with demonstrations of various trades, including making horseshoes and printing a newspaper.

In the following year, in May 1886, the Haymarket Riot in Chicago dealt a severe setback to the labor movement. But the commemorations in September continued, and in 1894 Congress designated the first Monday in September as a legal holiday to mark the contributions of labor.