| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Sheboygan | 1 | 49,265 | 49,946 | -0.22% | 3,043 | 16 | City |
| Plymouth | 2 | 8,796 | 8,939 | -0.28% | 1,641 | 5 | City |
| Sheboygan Falls | 3 | 8,795 | 8,199 | 1.24% | 1,601 | 5 | City |
| Howards Grove | 4 | 3,180 | 3,243 | -0.31% | 1,429 | 2 | Village |
| Oostburg | 5 | 3,054 | 3,063 | -0.07% | 1,507 | 2 | Village |
| Kohler | 6 | 2,292 | 2,185 | 0.88% | 431 | 5 | Village |
| Cedar Grove | 7 | 2,080 | 2,099 | -0.14% | 871 | 2 | Village |
| Random Lake | 8 | 1,573 | 1,563 | 0.06% | 1,048 | 2 | Village |
| Elkhart Lake | 9 | 1,227 | 947 | 3.11% | 920 | 1 | Village |
| Cascade | 10 | 700 | 723 | -0.57% | 851 | 1 | Village |
| Waldo | 11 | 483 | 466 | 0.63% | 496 | 1 | Village |
| Adell | 12 | 480 | 498 | -0.62% | 860 | 1 | Village |
| Glenbeulah | 13 | 450 | 461 | -0.44% | 647 | 1 | Village |
Sheboygan is the largest city in Sheboygan County, with a population of 49,265.
Glenbeulah is the smallest city in Sheboygan County, with a population of 450.
There are 13 cities in Sheboygan County, Wisconsin.