[4] It was first named Helvetia (pronounced hellveesha) in accordance with the heritage of the town's Swiss-German founding members.

The town voted to change its name to the English version, "Highland", in the early 20th century, as well as stopping production of its German language newspaper, in part to avoid negativity towards those of Germanic heritage at the advent of the First World War.

Highland has a rich history including extended visits by such notables as Abraham Lincoln.

[5] On November 21, 1915, the Liberty Bell passed through Highland on its nationwide tour returning to Pennsylvania from the Panama–Pacific International Exposition in San Francisco.

Highland Silver Lake is a reservoir constructed on the East Fork; the Highland city limits extend north 5 miles (8 km) to the southern border of Grantfork to enclose the entire lake.

Highland has been home to businesses that include Pet Milk and the Wicks Organ Company.

For the past 60 years, Highland Supply Corporation has been producing and selling floral grass - a traditional decorative product used to line Easter baskets.

Highland is also home to The Korte Company (builder of many large and well-known buildings including Universal Studios in Florida).

[7] Highland is in the process of implementing citywide availability of a municipal broadband network using Fiber to the home technology.

Highland is the setting for the first song on the Illinois album by Sufjan Stevens, titled 'Concerning the UFO sighting near Highland, Illinois', in which Stevens mentions a 21st-century UFO sighting by the owner of the local mini-golf course.

A report mentioned local pharmacist and state legislator Ron Stephens, who protested an executive order by Illinois Governor Rod Blagojevich requiring a pharmacist to fill emergency contraception prescriptions.