In the 1920s a large number of Northern Italian immigrants (originally from Modena) moved to Highwood, many from Dalzell, a coal mining town in Bureau Co to seek jobs. The National Prohibition of Liquor at the time also attracted boot-leggers who smuggled large scales of liquor into the city. The fight to prevent Highwood from being known as a whisky den largely brought the community together.
The main highway to Highwood is US-41, which connects Chicago to Milwaukee. Commuter rail is available at two different Metra stations locations within the city (Fort Sheridan and Highwood) . Highwood is also located near the Highland Park and Lake Forest stations which all located on the Union Pacific / North Line which begins in Kenosha and ends in the downtown area of Chicago at Ogilvie Transportation Center.
Highwood residents are served by the Township High School District 113 and the North Shore School District 112. Oak Terrace School, which is a part of the North Shore School District 112 school district services provides grades K – 5th. Highland Park High School serves as secondary education to the residents of Highwood however, it is a part of the Township High School District 113.
The Don Skrinar Recreation Center is a public facility located within the center of downtown Highwood. The city is also a host to the Midwest Young Artists (MYA) facilities and The Performer’s School. The Fine Art Studio of ROTBLATT-AMRANY, owned by Julie Rotblatt Amrany is located within the old village of Fort Sheridan.