Dutch settlers began moving to Highland shortly thereafter from nearby Munster.

[8] In 1927, President Calvin Coolidge visited and delivered the dedication address for Wicker Memorial Park, located on the west side of the town.

On October 31, 2008, Barack Obama, who four days later would be elected the 44th President of the United States, stopped in Highland for a rally that drew 40,000 people to Wicker Park.

As the railway tracks were abandoned since, the Erie Lackawanna Trail runs nowadays through downtown Highland instead.

Highland's downtown area features a number of buildings exhibiting Mid-Century Modern style architecture.

The area where the former Main School once stood is marked by a gazebo, which was demolished in October 2006 and rebuilt in 2007.

It and the surrounding land are named Main Square Park after the now-defunct school that stood on the site until 1977.

The other, Orchard Park Elementary, closed in 1981 and was later purchased and reopened as a Calumet Baptist School in the early 1990s.

Lake County Public Library operates the Highland Branch at 2841 Jewett Street.

[15] Wicker Memorial Park, at 8554 Indianapolis Boulevard, is owned and operated by the North Township trustee and was dedicated in 1927.

Featured are a 72-par, 18-hole golf course, three miles of trails, volleyball and tennis courts, a dog run, playground, splash pad, picnic areas and banquet facilities.

The Hoosier Prairie State Nature Preserve, established in 1976, is a 1,547-acre wetland prairie habitat located in an area in the vicinity of Main Street and Kennedy Avenue and partially in Highland, Griffith and Schererville.

Highland Parks and Recreation operates the Lincoln Community Center, Sharp Athletic Complex and the four-mile Erie-Lackawanna Trail.

The Main Square Park Gazebo is a popular site for wedding ceremonies as well as a number of community events and festivals during the year.