4 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Plentywood | 1 | 1,605 | 1,668 | -0.62% | 1,183 | 1 | City |
| Medicine Lake | 2 | 237 | 245 | -0.42% | 600 | 0 | Town |
| Westby | 3 | 159 | 167 | -0.63% | 283 | 1 | Town |
| Outlook | 4 | 79 | 82 | 0% | 63 | 1 | Town |
Plentywood is the largest city in Sheridan County, with a population of 1,605.
Outlook is the smallest city in Sheridan County, with a population of 79.
There are 4 cities in Sheridan County, Montana.