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A train sitting in front of the administrative building in Highwood. The Chicago, North Shore and Milwaukee rail company closed in 1963. Photo submitted
A conductor hanging out of the window of a Highwood route train. Highwood was the home of the rail line’s administrative staff.
Submitted Content
12:50 pm CST January 6, 2018

The Chicago, North Shore and Milwaukee Railroad was an integral component of Highwood’s history.

It began as the Bluff City Electric Railway Company in the late 1800s and became part of the Chicago and Milwaukee Electric Railway Company in 1898.  

Samuel Insull bought the company in 1916 and changed its name to the Chicago, North Shore and Milwaukee Railroad.