The area of what is now the Village of Toledo, located in the geographical center of Cumberland County, Illinois, was historically swamp land covered with tall prairie grasses. The Kickapoo Indian Tribe mainly inhabited the area until approximately 1832, the year of the Blackhawk War.  The Village was officially incorporated on June 10, 1866.

Toledo underwent several name changes in the 1800s. The town was first platted in 1849, and first officially platted on June 10, 1854, under the name "Prairie Village." Because this name conflicted with the name of another Village in the state, the Post Office called the present-day Toledo "Majority Point" for several years. On Aug. 27, 1881, the town passed an ordinance to change the name to Toledo.

Toledo began to substantially grow as a community in the second half of the 19th century. The first courthouse was built in 1855; this structure, which housed all of the county records and files, was completely destroyed in a fire on Nov. 4, 1885, and rebuilt in its present location in 1887. In 1859, the county chose Toledo to be the site of its first county jail. By 1862, the Village had completed a two-story, frame school building. And the railroad, known first as the Mattoon and Grayville and later as Peoria, Decatur, and Evansville, started running through Toledo on June 23, 1877.

Several businesses thrived in these early days of Toledo's history.  The oldest business institution in the county was the Toledo Democrat, originally called the Cumberland Democrat.  This newspaper has been published continuously since its 1857 inception. The Starger Mill, built in 1884, was located near a switch of railroad and was known as one of the best grist mills in the state. The Willis Brothers' Bank, founded in 1890, occupied a place on the town square until its liquidation and reorganization into First National Bank in 1933. The bank continues to serve Toledo today.

In 1901, an electrical light plant was constructed; water from the reservoir, which was constructed in the same year, powered the electrical plant. The reservoir was never used for its intended purpose of providing water, but instead attracted boaters and sunbathers and was the site of weekly band concerts during the summer. The reservoir has also been used to help fight fires in the Village. Today, the reservoir continues to provide recreational opportunities.

Toledo acquired its first public library in 1920, which was maintained solely by private donations and volunteer work. In 1923, the citizens of Toledo voted to support the library with tax dollars. Other businesses in Toledo near the turn of the century included lumberyards, meat markets, livery stables, furniture dealerships, barbershops, implement dealers, a hospital, a movie theater and shoe repair shops.

Since its beginning in 1866, Toledo has been successful in keeping the interests of the community a priority for decision makers of the Village. With the rich history of the area and community's vision for the future, Toledo should continue to prosper for years to come.