Wednesday, April 13, 2022

Theodore Roosevelt in Freeport, Illinois, in 1910.

After leaving the presidency in 1909, Theodore Roosevelt returned to Freeport on Thursday, September 8, 1910, to speak at a picnic to benefit the Brotherhood of Railway Trainmen held in Taylor Park.
Theodore Roosevelt standing on a table giving a speech.
Roosevelt, who was welcomed by Mayor W.T. Rawleigh, mounted a table and addressed a large crowd on the need for better citizenship and clean government.
Theodore Roosevelt is seated in the center for dinner.

Compiled by Dr. Neil Gale, Ph.D.


  1. Was this the occasion when T. Roosevelt described Highwood, IL. as "the toughest town in the United States?"
    I learned of this suggested quotation when visiting the Kings and Convicts Brewpub in Highwood in 2018.

    1. No.

      Highwood was founded in conjunction with Ft. Sheridan as a support community. The development of the Fort Sheridan affected Highwood's business district, which was soon filled with bars and taverns. Highwood's reputation led President Theodore Roosevelt (1901-1909) to call it “the toughest town in America,” in 1904. Highwood quickly became a typical army-base town and took its place in the Guiness Book of World Records as having the most bars per square mile. Chicagoans often referred to Highwood as “Whisky Junction.” Before agreeing to build the Great Lakes Naval Training Station in 1904, Congress insisted on passing the Highwood Act, which prohibited bars near military bases.

      Highwood set such an example that the federal government required legislation prohibiting new liquor establishments near military installations before they would consider enlarging Great Lakes Naval Training Station in North Chicago. While Fort Sheridan helped introduce the liquor industry to Highwood, the fort alone could not sustain the area taverns. From Evanston to Kenosha, Highwood was the North Shore's only wet community. Patrons came from all North Shore communities to have a drink and find a home away from home.

      Highwood's business district was running wild, many of its residents embraced the temperance movement. Members of the Methodist Church and the Lutheran Church and local Baptists joined together to fight alcohol. Community members attempted to bring in an eminent temperance leader to open a Bible retreat in an area that is now the southernmost region of Fort Sheridan.


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