• First Reformed Church of Roseland (1887, now Lilydale Progressive M.B. Church)
• South Michigan Avenue Commercial District
• Jan Ton farm / Underground Railroad site (Little Calumet River)
• The High Prairie ridge along Michigan Avenue

Roseland was settled in 1849 by nine Dutch immigrant families who called their new home "de Hooge Prairie," the High Prairie, for its higher, drier ground compared to their earlier settlement to the south. The community remained a farming village for decades until 1873, when real estate developer Colonel James H. Bowen suggested renaming it Roseland after the abundant flower gardens the Dutch settlers had planted around their homes. Roseland was annexed to Chicago in 1892.

Long before that renaming, Roseland farmer Jan Ton sheltered freedom seekers on his land along the Little Calumet River, guiding them onward toward Canada as part of the Underground Railroad. The First Reformed Church of Roseland, built in 1887 by the community's Dutch settlers at 107th Street and Michigan Avenue, still stands today as Lilydale Progressive Missionary Baptist Church. Nearby, the South Michigan Avenue commercial corridor grew into Roseland's retail heart between the 1880s and 1930s, serving the tradesmen drawn to the area by the nearby Pullman car works.

From a Dutch farming village on the High Prairie to a hub of industry and a station on the road to freedom, Roseland's history runs far deeper than its distance from downtown — a legacy worth wearing on your own high ground.