The sycamores here line the sides of the Michigan Road, which connected the Ohio River with Lake Michigan and further opened Indiana for white settlement and trade. Under intense military and economic pressure, Potawatomi leaders ceded the land for the road in 1826. John Tipton, one of the U.S. agents who negotiated this treaty, purchased the land here in 1831. The state began work on the road in the 1830s. While there are several theories on how the trees came to be here, their origin is uncertain. By the 1930s, road improvements threatened the trees, but residents organized to preserve them over the following decades. In 1983, the Carroll County Historical Society petitioned to reroute the highway and saved Sycamore Row.