The Pleasant Prairie area was highly active with Native American activity in pre-pioneer Wisconsin. The remnants of Native American culture abound in Pleasant Prairie. Some of the earliest traces of Native American life in Wisconsin were found along STH 32 and STH 165 and in the Carol Beach area. These early Indian campsites, along what was once the shoreline of Lake Michigan, represent some of the highest quality archeological sites in the United States. In addition, several natural historic sites such as the Chiwaukee Prairie and the Kenosha Sand Dunes lie undisturbed in Pleasant Prairie and provide Wisconsin residents with an opportunity to see what Wisconsin looked like before the arrival of our earliest settlers.

Pleasant Prairie originally was a township that was nearly 42 square miles in size. Over the years, the city of Kenosha began to annex lands south of 60th Street and west from Lake Michigan, and the Town of Pleasant Prairie slowly reduced in size over the next 150 years as the City of Kenosha grew. There were nine separate settlement areas in the township that in some cases became the starting point for significant growth in the future, and some no longer exist at all.

The most colorful area was the old village area of Pleasant Prairie located at 104th Avenue and Bain Station Road. The Pleasant Prairie Powder Plant was located in this area which exploded after the turn of the century and rocked buildings and shattered windows miles away. Today it is the location of many residential homes and the Pleasant Prairie Ball Park where many children play recreational softball and soccer.

Another old settlement area is the Bain Station and Ranney areas. Its location was along Bain Station Road between the current Canadian Pacific and Union Pacific railroads. These settlement areas were not as residential as they were rail stops for the Chicago Northwestern, the Kenosha-Harvard line, and the CSMP&P Chicago-Milwaukee main line. The Ranney site ended as a stop prior to 1862 and Bain Station site was named for the Bain Wagon Works and was listed as a stop well after 1800s. It is now the end of the line for trains coming out of Kenosha. The current site is immediately north of the Pleasant Prairie Power Plant and south of the power plant landfill.

Another more recent settlement area is the Carol Beach area that is along Lake Michigan from the Kenosha city limits to the state line. A subdivision of Carol Beach is the Chiwaukee area which was plotted in the 1920s. The rest of Carol Beach was subdivided and began plotting in 1947. The area is one of the most significant wetland areas in the United States and was largely protected through a compromise land use agreement between the Town of Pleasant Prairie, Kenosha County, the State of Wisconsin, and the Army Corp of Engineers. Today many of the areas that can be developed have been, and the state of Wisconsin and the Nature conservancy continue to buy remaining properties for prairie land preservation.

Other areas of the old township such as Tobin, Truesdell, Erly, and State Line have been incorporated within the Village of Pleasant Prairie.

Pleasant Prairie had its beginnings as a political entity in April 1842 when the first town meeting was held and the first election of township officials took place. The early township officials met in the Williams' Congregational Church located at 93rd Street and Green Bay Road, which now is a religious bookstore. Later the old church became the official Town Hall and served the quiet agricultural community until urban growth finally necessitated more modern quarters in 1961. In that year, the Town rented office space in a small commercial center located on 22nd Avenue and 91st Street. That office space currently is a hair styling salon. In 1967 the Town government moved into a newly constructed municipal building on Springbrook Road and 39th Avenue that provided office, an auditorium, Fire Department apparatus room, and sleeping quarters. Finally, in 1997, eight years after the incorporation of the Town into a Village, the Municipal Building was updated and increased in size to accommodate Village operations.

As a Town, Pleasant Prairie constantly struggled to maintain its identity and ability to provide for the orderly development of the community. In 1984, the town and the City of Kenosha agreed upon a plan for orderly development and fixed boundaries for the Town in exchange for the acknowledged right of property owners in various locations along the Town/City border to annex into the City of Kenosha. The most significant area of this agreement was giving the City of Kenosha the ability to annex lands north of STH 50 from Green Bay Road to I-94, where the current Southport Plaza shopping center, White Caps subdivision, River Crossing subdivision among others, and the Aurora Hospital are located. In exchange the Town received the ability to protect the rest of the Town from annexations and the ability to purchase sewer and water from the City of Kenosha. In 1989, the agreement was advanced and the Town of Pleasant Prairie was incorporated as a Village by a referendum of more than 3,000 citizens in favor and 300 against. The new boundaries were fixed and the Village, with Wispark Corporation, began the development of LakeView Corporate Park, a large, modern, and beautifully landscaped center of employment for more than 8,000 people. Based on property value, Pleasant Prairie ranks as the fifth largest manufacturing municipality in the State of Wisconsin, exceeded only by Milwaukee, Green Bay, Madison, and Menomonee Falls.