Most of Fort Sheridan’s western border lies along Sheridan Road, east of where Green Bay Road, which winds along the top of the morainal ridge, ends in Highwood. The high ground to the east was used by Native Americans who traveled between their villages and hunting grounds to trading posts. During the early to mid-1800s, troops provided safe passage for traders and early settlers, and for a short time the trail was known as Military Road. After 1833, when the Potawatomi signed away Lake County, Cook County, and all that remained of their land in Illinois, trade and traffic along the road increased significantly.
The earliest settlers were mostly immigrants from Ireland, Germany, and Scandinavian countries. Because the land of Fort Sheridan and other sections of the Bluff Coast had steep ravines and thriving forests that would have been difficult to clear, the settlers in the mid-1800s never considered the land useful for farming. As a result, the Fort Sheridan site was never plowed, unlike much of the rest of Illinois.
In the late 1800s, wealthy families sought out the lake bluffs and began to build country-style estates in such areas as Lake Forest and Highland Park. Some estates were occupied year-round, while others were used as summer homes. The scenic bluffs overlooking Lake Michigan are still regarded as choice real estate and provide an example of how geology and nature can influence development.