The Pottawattomie Tribe occupied these lands, and remained here until the area was ceded to the United States government in 1833, from approximately Kenilworth north to the State Line. A few Native Americans still returned each year to the hunting grounds. The only road in those days was the Green Bay Trail which ran from Fort Dearborn in Chicago to a federal trading post in Green Bay, Wisconsin.

The first non-native American settlers came to Highwood in 1846. The Stupey family selected a site for their farm in the wooded, rolling hills two days’ journey north of Chicago. It was a surprise to the Stupeys to find that they had built their cabin on an ancient Indian trail. In 1851 work began on the Chicago and Milwaukee Railway. The workers who built or were employed by the railroad began to settle in Highwood. The increase in transportation service made Highwood more appealing to Chicagoans who wanted to move out of the city.

In the late 1860’s, E. Ashley Mears and Reverend William W. Everts platted 20 acres near the Stupey farm as speculative real estate. The area measured one mile north and south by a half mile east and west.

Thomas Curley suggested the name High Woods because the land was the highest ground between Chicago and Milwaukee and was covered with trees. The name became Highwood and was filed with the town’s first plat map on August 22, 1868. The village of Highwood was incorporated in 1887.

In 1886 civil and labor unrest in Chicago resulted in the Haymarket Riot. Chicago businessmen felt that a military presence near the city would help alleviate the tension. They purchased land in Highwood for a camp and members of the Sixth Infantry Regiment arrived at ‘Camp Highwood’ on November 8, 1887.

Camp Highwood was officially named Fort Sheridan on February 27, 1888, in honor of General Philip Sheridan for his service in maintaining order after the Chicago Fire of 1871. The construction of permanent buildings at the Fort brought the first large wave of immigrant settlers to Highwood.

Highwood provided business and employment opportunities. Bricklayers, carpenters, and hod carriers grew tired of traveling back to Chicago after a day’s work and settled with their families in Highwood. The city also attracted residents who lost their homes during the Chicago Fire. Many of these immigrants were of Swedish and Irish descent. In 1901, 225 of Highwood’s 851 residents were foreign-born, most of whom were Swedish.

Highwood was both enriched and challenged by its proximity to Fort Sheridan. Business and job opportunities were abundant and the city prospered. With the addition of the Chicago and Milwaukee Electric Railway (North Shore Line), the city flourished. However, with prosperity came new challenges. The sudden rise of saloons, gambling dens and illegal “blind-pig” taverns catering to off-duty soldiers caused concern not only for Highwood but also for its temperance-minded neighboring communities. Eventually, Federal authorities enacted the “Highwood Quadrangle” prohibiting the sale of liquor within one and one-eighths of a mile radius from the army base.

An amusement center named Fort Sheridan Park attracted hundreds of people for band concerts, vaudeville shows, and dancing in an open-air pavilion. Trolley coaches also carried liquor-seeking patrons which created further problems for the police. On July 18, 1888 the trustees voted to change the name from Highwood to the Village of Fort Sheridan to capitalize on the “military glamour” associated with the dashing cavalry troops. Within six years the name was changed back to Highwood due to residents’ frustration and confusion with postal mis-routing.

The second wave of immigration occurred in the 1920’s. Northern Italians from the region of Modena came to seek employment. Men skilled in masonry, carpentry, and landscaping secured jobs on the large estates of Lake Forest and Highland Park. Women found work as domestic help. Many opted to open their own businesses and cater to the needs of the growing community. The closing of the coal mines in Central and Southern Illinois brought more immigrants looking for work. Several of their stories have been documented in Adria Bernardi’s Houses With Names.

The National Prohibition of Liquor in the 1920’s gave rise to a more serious problem. Boot-leggers, chiefly attracted by the army base, began large-scale smuggling of liquor into Highwood. The fight to end Highwood’s reputation as a “whisky-den” helped to unify civic organizations and residents.

Highwood, as were many communities across the nation, was deeply affected by the Great Depression. Citizens united in civic and church organizations to support each other and needy families. Through the Works Progress Administration (WPA), Highwood received funds to improve roads and install sewer lines. Funds were also provided to build the Highwood Water Plant at the foot of Walker Avenue. Although civic progress slowed, community spirit was raised by its strong participation and pride in sporting activities.

With the declaration of World War II in 1941, residents’ attention was diverted from the Depression to the more critical conflict abroad. Artillery blasts resounded daily from Fort Sheridan’s active training ground. Civil Defense projects and a Red Cross Unit occupied homefront interests while local men left for the battle zones. The influx, deployment, and separation of troops led to the creation of a servicemen’s center. The combined efforts of hundreds of residents helped to successfully entertain thousands of servicemen each month at the Highwood USO. This was a time of great economic prosperity for Highwood. Businesses boomed and the population soared.

The opportunities in Highwood again attracted another wave of immigrants. Some arrived from war-weary villages in Europe and others from Mexico, mostly from the state of Guerrero, doing much of the same work the Italians did earlier in the century. As with their predecessors, they brought their strong work ethic, family values, and hopes for a better future.

During the decades that followed the city once again reinvented itself. There were political changes, the business district took on a new look, many businesses remained and new ones opened. Highwood’s restaurants have become the destination for North Shore diners. Art fairs and various Festivals are the norm. Change is inevitable and Highwood stays ready to meet the challenge.

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