The Deer Path Inn had its beginnings as a private home on Illinois Road. The original building was constructed in 1869 as a home for the Colonel William Sage Johnston family. In the 1890s, the family sold their large lot to the City of Lake Forest, which planned to build a school there. The house was moved one block to the north to front on Deerpath road. An enterprising woman named Mrs. Brewster converted it into a hotel known as the “Brewster House.” With the New Hotel burning in 1877 and the Old Hotel growing rundown as a boarding house, her hotel filled a need for temporary and vacation quarters in Lake Forest.

By 1900, Mr. W. C. DuBrock was operating the Brewster House, charging $2 a day. To relieve overcrowding in the Lake Forest schools, from the fall to the spring in 1899 and 1900, local children attended classes at the hotel. Construction finally began on the new Central School (now Gorton Community Center) in 1901.

Capitalizing on the weekend and summer traffic from the Onwentsia Club golf course, Mary Patterson took over the hotel in 1901 and called it the “Golf Inn.” This name did not last, being supplanted in 1903 by "Deerpath Inn." She, along with her daughter Kate and son Roy, operated the Inn into the 1920s.

The Deerpath Inn became a retreat for wealthy Chicagoans and guests visiting Lake Forest for both short and long-term stays. Its restaurant hosted dinner parties, and local entrepreneurs held pop-up shops. Optometrist Dr. A. H. Merrar saw patients at the Inn every Monday in 1919.

In 1924, Edwin Burgess purchased the inn and, due to increasing demand, within five years determined to build a larger hotel at new location on Illinois Road.