18 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Chestertown | 1 | 5,747 | 5,537 | 0.79% | 1,969 | 3 | Town |
| Chestertown | 2 | 5,747 | 5,519 | 0.79% | 1,969 | 3 | Town |
| Kingstown | 3 | 1,909 | 1,853 | 0.58% | 842 | 2 | CDP |
| Rock Hall | 4 | 1,203 | 1,194 | 0.25% | 899 | 1 | Town |
| Rock Hall | 5 | 1,203 | 1,188 | 0.25% | 899 | 1 | Town |
| Chesapeake Landing | 6 | 620 | 132 | 7.08% | 619 | 1 | CDP |
| Millington | 7 | 540 | 546 | -0.18% | 591 | 1 | Town |
| Millington | 8 | 540 | 544 | -0.18% | 591 | 1 | Town |
| Galena | 9 | 538 | 540 | 0% | 1,490 | 0 | Town |
| Galena | 10 | 538 | 538 | 0% | 1,490 | 0 | Town |
| Butlertown | 11 | 522 | 328 | 0.19% | 638 | 1 | CDP |
| Kennedyville | 12 | 520 | 423 | 4.21% | 1,018 | 1 | CDP |
| Tolchester | 13 | 488 | 435 | 2.31% | 800 | 1 | CDP |
| Betterton | 14 | 283 | 285 | 0% | 286 | 1 | Town |
| Betterton | 15 | 283 | 283 | 0% | 286 | 1 | Town |
| Fairlee | 16 | 228 | 519 | -6.94% | 60 | 4 | CDP |
| Still Pond | 17 | 158 | 119 | 7.48% | 854 | 0 | CDP |
| Worton | 18 | 69 | 98 | -14.81% | 75 | 1 | CDP |
Chestertown is the largest city in Kent County, with a population of 5,747.
Worton is the smallest city in Kent County, with a population of 69.
There are 18 cities in Kent County, Maryland.