It was originally settled by Emory Cobb, who used the land as pasture before deciding to erect a resort hotel.

At this time the Illinois Central Railroad built a station, spurring rapid growth.

Early settler Lemuel Milk drained marshes in the area to create a habitable space along the Kankakee River.

He moved to Kankakee at this time and built his house at the southwest corner of what is now River Street and South Chicago Avenue.

Heavily involved in Kankakee's early commercial development, Cobb decided to build a resort hotel on his property.