Sylvester Lind loomed large in early Lake Forest history. He was the town’s most frequent mayor, serving four terms. Roadside, his home on Deerpath, was a common gathering place. It was said that Lind, who often traveled the Green Bay Trail between Chicago and Milwaukee on horseback for banking business, was the first to suggest the future site of Lake Forest. He was a charter member of the Lake Forest Association and key proponent of Lake Forest’s educational mission, lending his money and his name to the college, called Lind University in it earliest years.

Born in Scotland in 1808, Lind came to Chicago in 1837 and found work as a carpenter. The ambitious young man entered the lumber business and by 1849 had organized the firm of Lind and Dunlap, with mills at Cedar River in Wisconsin. He also had a hand in the banking and insurance businesses, losing and gaining at least three fortunes in the boom and bust cycle of early Chicago.

By the early 1850s Lind erected a building at the northwest corner of Randolph and Wacker known as the Lind Block. At seven stories, it was one of the first Chicago “skyscrapers,” and one of the only downtown structures to survive the Chicago Fire in 1871.

From 1857 until 1865, today’s Lake Forest College was known as Lind University. Sylvester Lind had pledged $100,000 to fund a Presbyterian institution of higher learning in the new community of Lake Forest. A nationwide economic depression in 1857 threw a wrench into these plans. Further, the collegiate department did not survive the decline in enrollment caused by students going off to fight in the Civil War. In 1865 the state charter was altered to change the name. The newly christened Lake Forest University would at long last open its doors in 1876. The mayor of Lake Forest who helped make that happen? Sylvester Lind.

Sylvester Lind held strong anti-slavery beliefs and was a key figure in Chicago’s Underground Railroad. He used his lumber shipments as cover to assist escaped slaves on their journeys, arranging for the ships’ captains to look the other way for deniability as they sneaked aboard. The escaped slaves made their way from Lind’s lumber yard in Chicago to the lumber mills in northern Wisconsin, and on occasion all the way around the Great Lakes to Detroit and Ontario.

Sylvester and Eliza Lind’s home, Roadside, was built at the site of today’s 550 East Deerpath in 1859, one of Lake Forest’s first residences. Early Lake Foresters met there to discuss whether to incorporate as a city. According to one source, the later reminiscences of Rev. James McClure, who came to Lake Forest in the 1880s, Lind’s home was also rumored to have briefly served an Underground Railroad stop.