An extensively altered mid-19th century country inn, it was from 1880 until his death in 1903 the principal residence of Henry Demarest Lloyd (1847–1903).

Lloyd was a leading "muckraking" journalist of the late 19th century, and a major editorial voice against corporate monopolies and for organized labor.

[2][3] The Wayside is located on the west side of Sheridan Road, at its junction with Lloyd Place in central eastern Winnetka.

[3] Henry Demarest Lloyd was a native of New York City, and received a law degree from Columbia University.

The Lloyds hosted many prominent individuals of the time here, including Booker T. Washington, Charlotte Perkins Gilman, and Walter Crane.