It includes the cities of Sheboygan Falls, Plymouth, and Kiel, and the villages of Oostburg, Elkhart Lake, Howards Grove, and Kohler.

It also contains Lakeland University, the Blackwolf Run golf course, the Road America motorsport course, and the Sheboygan County Memorial Airport.

[2] The district is represented by Republican Lindee Brill, since January 2025.

Following the 1982 court-ordered redistricting, which scrambled all State Assembly districts, the 1983 redistricting moved the 27th district to Sheboygan County, comprising the rural towns surrounding the more suburban municipalities of Sheboygan, Kohler, and Sheboygan Falls.

Act 43) split the city of Sheboygan between the 26th and 27th districts, in order to create two safe Republican districts from what had previously been the competitive 26th and safe Republican 27th.