830 Sheridan

830 Sheridan Road is easily one of the most famous houses in Winnetka. This house, known as “Wayside,” is named after the tavern owned by John Garland, the first resident of the original portion of the house at 830 Sheridan.

Originally built in 1850s, Wayside started as a two-story brick structure that measured approximately 21 x 31 feet. Significant portions were added in the 1880s, and the house went through a large remodel in 1890 to make it more cohesive.

As one of the oldest houses in Winnetka, 830 Sheridan is interesting in its own right. This house is made even more fascinating, however, due to its most famous resident, Henry Demarest Lloyd, who bought the house in 1878 and lived there until his death in 1903. Lloyd was quite an important character in the history of Winnetka. He began his career as a journalist in New York City where he fought against corruption and helped the working people of the city gain access to public libraries. In 1872, however, he left the Big Apple and moved to Chicago, where he joined the staff of the Chicago Tribune. Lloyd married women’s rights activist Jessie Bross one year later and the couple moved into Wayside shortly after.

While living in Winnetka, Lloyd made a name for himself as one of the first “muckraking” journalists. Lloyd advocated for reform through both journalism and books. He pushed the envelope in support of labor unions, which landed him in hot water with his father-in-law William Bross, who was also editor and founder of the Tribune. He left the paper in 1885.

Shortly after, Lloyd proved controversial again when he set about defending the anarchists accused of bombing Haymarket Square. Such opinions left himself and Jessie ostracized from Chicago society. After leaving the Tribune, Lloyd continued to write on his own terms. His most famous book, Wealth Against the Commonwealth, was published in 1894.

While the Lloyds were no longer welcomed by Chicago society, they were quite well respected by their friends and neighbors in Winnetka. Lloyd’s friend and fellow Winnetkan Frederick Greeley once remarked about Wayside: “No one cared what he had or how he looked but each one felt that he gave and received value in this clearing house of ideas, where both poor and rich got richer and no one lost.” In addition, social reformer Jane Addams remained a supporter of Lloyds, even referring to Wayside as an annex for her famous social settlement, Hull House.

While Lloyd was consistently busy with his work, he was nonetheless dedicated to his community. He participated in the development of the Village Improvement Association, the Winnetka Town Meeting, and the Fourth of July celebration. He was also instrumental in the formation of the municipally owned water and electric plants.

Incredibly, Lloyd’s children and grandchildren maintained ownership of the house until the 1970s. Because of its unique original and remodeled construction, as well as its association with Lloyd, this vernacular Victorian house became Winnetka’s first National Historic Landmark in 1976.