1780 – Chief Ish-Tak-Ha-Ba was born at Swan Lake in Nicollet County. Ish-Tak-Ha-Ba was a member of the band of Dakota Native Americans. At 6’2”, he grew to be a large and well proportioned man, of rather dignified appearance, was good natured and plausible, but lacked distinction as a hunter or warrior. It was believed that his eyelids drooped slightly and his name, Ish-Tak-Ha-Ba, which translates in English to Sleepy Eyes, was derived from this physical characteristic.

1824 – Chief Sleepy Eyes went to Washington DC to receive a document from President Monroe declaring that he was officially a chief, succeeding Blue Spirit. He then became chief of all of the Lower Sisseton Sioux (Dakota) from Carver to Lac-Qui-Parle.

1857 – Chief Sleepy Eyes was asked to move his camp to a lake west of his village, which was later named after him, as was the town which was erected years later near the lake. In the Dakota language, the word Sisseton means swamp-dweller. The Sisseton people lived in or near sloughy areas and Chief Sleepy Eyes settled on the north side of Sleepy Eye Lake, near the present site of Sportsman’s Park campground.

1860 – Chief Sleepy Eyes died on an island in Bullhead Lake in Roberts County, South Dakota in the tepee of a very old Indian Chief named Red Eagle. Red Eagle had dressed Sleepy Eyes in one of his own new buckskin suits, and in this he was buried under a large tree. Also buried with Sleepy Eye was his pipe, a small mirror, his tobacco pouch of raccoon skin, on which the head was left as an ornament, together with beads and other small articles. Chief Sleepy Eyes was buried in a sitting position.

1862 – Earliest travel in Minnesota was by waterways or across country until the railroads became a reality. Because of that, the pioneers settled near these transportation modes. Sleepy Eye was no exception. A few families acquired land near Sleepy Eye Lake.

1864 – Thomas Allison, one of the earlier settlers, decided there should be a town located by the lake. He took his idea to the railroad’s attorney, Walter Brackenridge of Rochester, MN. After listening to his ideas, Brackenridge agreed with Allison and purchased some land from him. They, with the help of others, set about the task of platting the area.

There was also a need for a Lutheran church. The first church built by St. John’s Lutheran parish had had living quarters in it, but as soon as a parsonage could be built that part of the church building became a school. That was in 1885, nine years after the church was built.

1883 – Members of the Catholic Church became interested in building a parish school. A building was erected, containing four classrooms on the first floor, while the second floor was home for the sisters who taught at the school. About 90 pupils enrolled and were taught under the direction of the Sisters of St. Francis of Rochester, MN.

The Sleepy Eye Flour Milling Company began operations in 1883.

1887 – A second depot for the railroad was built and used as a freight depot for many years. It still remains today, housing the Depot Antiques, a repository filled with antiques, primitives, antique lighting and much more.

1894 – The Sleepy Eye Flour Milling Company owned 27 elevators in Minnesota and South Dakota. It had its own cooper’s shop in which it made the barrels for the flour. Although capacity was 5000 barrels of flour daily, not all flour was packed in barrels. Many of the brands produced by the Sleepy Eye Flour Mill, including Cream, Apple Blossom, Gold, Snowflake, Chief and Cyclone Brands of flour, were sold in cloth sacks. The mill also produced cereals, Pancako, and Koffeeno. The mill ran night and day, six days a week, and shifts were usually 12 hours.

1895 – On May 17, an explosion occurred at the Public School and it burned to the ground. A new school was built that same year and remained till 1982 when it was demolished and a new one story school was built.