The Town Of Highwood, Illinois

Highwood is a Chicago North Shore suburb, located in Lake County, approximately 28 miles (45 kilometers) due north of downtown Chicago. Neighboring communities are Highland Park and Lake Forest. Sheridan Road and Green Bay Road, the historical north-south roads that evolved to carry traffic between Chicago, the north suburbs, and Wisconsin, pass through the city.
The City of Highwood is served by Metra’s Chicago & North Western/North Line commuter trains and Pace bus service. Major highways accessible are IL Rte. 22, IL Rte. 131 and U.S. Rte. 41.

• Distance to the Chicago Loop: 27 miles
• Distance to O’Hare Airport: 20 miles
• Distance to Mitchell Field: 53 miles

The Highwood Recreation Center adds new programs each season to its list of offerings for its residents. Baseball, basketball, and karate programs give youths an opportunity to develop their skills and encourage team spirit. Children in grades K-5 may join the Summer Day Camp programs which include crafts, field trips, games, and the Tot Lot in Everts Park.

The public is welcome to enjoy the 18-hole Lake County Forest Preserve course at the Fort Sheridan Golf Club, and the Robert McClory Bicycle Path, connecting the southern border of Wisconsin to Wilmette, runs through Highwood immediately east of the railroad tracks.


School Address Phone Grade
Oak Terrace Elementary School 240 Prairie Ave, Highwood, IL 60040 (847) 433-0930 Elementary Schools
Oak Terrace School 940 Prairie Avenue, Highwood, IL 60040 847) 433-0930 Elementary Schools
Highwood History

“At the highest point between Chicago and Milwaukee you will find Highwood at the top of the Skokie ravine. This quiet North Shore residential community consists of beautiful homes made from stone, brick, and masonry by local Italian stonemasons. Fort Sheridan shaped the community of Highwood. Its business district was once called “Whiskey Junction” due to the popularity of its bars and taverns. Potawatomi lived in the area until the 1833 Chicago Treaty. They lived along the Green Bay Trail. Irish and German immigrants were interested in Highwood because of the work they could get as construction workers on the Chicago & Northwestern Railroad. In the years that followed, workers became the domestic labor force for the elite suburbs along Chicago’s North Shore.

The 1886 Haymarket Riot led to the development of Fort Sheridan. It was used as a massing point for federal troops so they could use it to put down urban disturbances. The primary source of income for Highwood residents came from employment at Fort Sheridan and the north Shore estates. Fort Sheridan’s development affected Highwood’s business district. It was soon filled with bars and taverns. Due to Highwood’s reputation, President Theodore Roosevelt called it the “toughest town in America.” The federal government, after seeing what was going on in Highwood, now required legislation prohibiting new liquor establishments near military installations before they would consider enlarging Great Lakes Naval Training Station in North Chicago. Highwood was the North Shore’s only wet community. People from all over North Shore came to have a drink and find a home away from home. While Highwood’s business district was running wild, members of the Methodist, Lutheran, and Baptist churches joined to help fight alcohol. Community members attempted to open a Bible retreat in an area that is now the southernmost region of Fort Sheridan.

In 1905, Highwood’s ethnic makeup changed when the first Italian immigrants arrived. They brought the craftsmanship of gardening and stonemasonry. Wealthy communities up and down the North Shore utilized the talents of these Italians. As WWII soldiers were being discharged, their first stop would be Fort Sheridan. Their pockets were full of money and they were ready to spend it all at the taverns and bars. The business district was booming.

After WWII, the community residents did not like the reputation their community of Highwood had acquired over the years. By the time the 1970’s came, city officials began to ask the bars to serve food. Within years, Highwood had many of the areas best restaurants outside the city of Chicago. With the closing of Fort Sheridan in 1993, Highwood doubled in size with the annexation of the Fort Sheridan subdivision.”

Highwood Trivia & Fun Facts

“Highwood was once in the Guinness Book of World Records for having the most bars in a community.

The area historical tornado activity is slightly below Illinois state average, but 43% greater than the overall U.S. average.”