| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Winona | 1 | 3,657 | 4,451 | -3.64% | 271 | 14 | City |
| Duck Hill | 2 | 1,576 | 656 | 11.46% | 1,524 | 1 | Town |
| Kilmichael | 3 | 531 | 634 | -3.28% | 181 | 3 | Town |
Winona is the largest city in Montgomery County, with a population of 3,657.
Kilmichael is the smallest city in Montgomery County, with a population of 531.
There are 3 cities in Montgomery County, Mississippi.