4 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Plentywood | 1 | 1,615 | 1,668 | -0.68% | 1,190 | 1 | City |
| Medicine Lake | 2 | 238 | 245 | -0.83% | 603 | 0 | Town |
| Westby | 3 | 160 | 167 | -1.23% | 285 | 1 | Town |
| Outlook | 4 | 79 | 82 | -1.25% | 63 | 1 | Town |
Plentywood is the largest city in Sheridan County, with a population of 1,615.
Outlook is the smallest city in Sheridan County, with a population of 79.
There are 4 cities in Sheridan County, Montana.