According to his daughter Harriet, in 1886 Julian Matthews arrived in Lake Forest “in a boxcar full of fine Virginia horseflesh.” Matthews was born enslaved in Virginia in 1863. By the 1880s, he was living in New Jersey, working for Reverend William C. Roberts, who had been at Princeton before being appointed President of Lake Forest University in 1886. Julian Matthews and his wife Octavia, then newlyweds, accompanied Rev. Roberts to his new post in the Midwest, Matthews traveling by train with the horses.

 

Once in Lake Forest, Julian and Octavia Matthews continued to work for Rev. Roberts, who as LFU President lived on campus in Patterson Lodge, then the President’s House and now the Office of Admissions. The Matthewses would have resided in a carriage house nearby (now demolished), where Julian likely cared for the horses and worked as a driver, and Octavia probably cooked and ran Rev. Roberts’ household.

In 1892 Rev. Roberts left Lake Forest, but Julian and Octavia Matthews stayed on. They were an entrepreneurial couple who soon had carved out a niche in the community for their large family of eight children (Eva, Carrie, Ben, Harriet, Mary, Juliet, Oliver, and Walter). From their new home base, a frame building on Western Avenue across from the Lake Forest train station, the Matthews family had multiple revenue streams: Octavia ran a restaurant and bakery and Julian a livery service (see ads above from The Stentor). They even merged the two in what Lake Forest College students labelled “The Dope Cart” – a wagon full of freezers of ice cream that would visit campus for baseball games (pictured in the above photo from the 1907 Lake Forest College student yearbook). Matthews also took a concession wagon out to the Onwentsia Club for events like the Lake Forest Horse Show.

 

Although ice cream was less in demand as the days grew shorter, the Matthews business model was adaptable. Julian moved summer people to and from Chicago as seasons changed; conducted sight-seeing tours of the town; and owned two sleighs for transporting clients on snow-covered roads in the winter. Octavia focused on her renowned baked goods. One of her customers was the Deerpath Inn, although, according to her daughter, the hotel clientele often did not receive many of her confections: “The hotel [staff] ate up all our bread and bought other bread to serve.”

 

The Matthews children also had their roles, as donut-turners and ice cream-scoopers. The family lived on Western Avenue above the restaurant, and Harriet Matthews Caldwell recalled sitting “in the upstairs window to watch the activity as horses and buggies lined up to meet the men as they arrived on the train from Chicago” – her father’s livery among them.

In the 1910s, the Lake Forest Improvement Trust bought out several storefronts on Western Avenue, including the Matthews’, to clear the way for Market Square. This led the family to pivot. They acquired a large lot at Illinois and Washington, located in the heart of one of Lake Forest’s African American neighborhoods. They built their home at 635 Illinois Road and a large, two-story carriage house/garage in the rear of the property. 

 

Here the Matthews family relocated the ice cream parlor and transformed the livery into a “cab line” for the automobile age. Soon they also added the Green Lounge music hall, on the upper floor of the carriage house. This became a happening place in the 1920s and 1930s, hosting acclaimed musicians and, according to the Chicago Defender, popular among the “younger-marrieds” for “cocktail hour” (after Prohibition was repealed in the 1930s, of course).

 

Though their businesses were very successful, the family did encounter racial prejudice. In 1939, a former resident named Lillie Russell wrote a letter to the editor of the Lake Forester which included memories of her childhood in Lake Forest, including some fond ones of Mr. Matthews and his donuts. “Incidentally,” she wrote, “you might ask him privately if he remembers how Mrs. French tried to get him to emigrate to Liberia? I’ll bet he’s glad he stayed in Lake Forest!” (The French family owned a drug store on Western which may have been a competitor to the Matthews’ ice cream parlor.)

 

In a 1970s oral history interview, Harriet Matthews Caldwell recalled always feeling very much at home in Lake Forest. “Everybody was just as congenial, you would never know there was a difference [regarding race]. You see my parents had been here so long–they were really pioneer–and everybody was very nice–rich, poor–we had no trouble living here at all.”