City | Rank | County | 2024 Pop. |
|---|---|---|---|
| Gillette | 1 | Campbell County | 33,501 |
| Sheridan | 2 | Sheridan County | 19,801 |
| Buffalo | 3 | Johnson County | 4,685 |
| Newcastle | 4 | Weston County | 3,315 |
| Wright | 5 | Campbell County | 1,654 |
| Sleepy Hollow | 6 | Campbell County | 1,404 |
| Powder Horn | 7 | Big Horn County | 1,178 |
| Sundance | 8 | Crook County | 1,120 |
| Moorcroft | 9 | Crook County | 1,018 |
| Story | 10 | Sheridan County | 1,009 |
| Upton | 11 | Weston County | 887 |
| Pine Haven | 12 | Crook County | 558 |
| Hulett | 13 | Crook County | 332 |
| Kaycee | 14 | Johnson County | 292 |
| Hill View Heights | 15 | Custer County | 225 |
| Clearmont | 16 | Sheridan County | 125 |
| Arvada | 17 | Sheridan County | 9 |
| Osage | 18 | Weston County | 4 |
| Big Horn | 19 | Sheridan County | 2 |