City | Rank | County | 2024 Pop. |
|---|---|---|---|
| Middlesborough | 1 | Bell County | 8,898 |
| Corbin | 2 | Whitley County | 7,843 |
| Williamsburg | 3 | Whitley County | 5,116 |
| Barbourville | 4 | Knox County | 3,124 |
| North Corbin | 5 | Knox County | 1,985 |
| Harlan | 6 | Harlan County | 1,812 |
| Cumberland | 7 | Harlan County | 1,780 |
| Pineville | 8 | Bell County | 1,581 |
| Pine Knot | 9 | McCreary County | 1,460 |
| Stearns | 10 | McCreary County | 1,192 |
| Whitley City | 11 | McCreary County | 1,144 |
| South Wallins | 12 | Harlan County | 996 |
| Flat Lick | 13 | Knox County | 870 |
| Evarts | 14 | Harlan County | 815 |
| Burnside | 15 | Pulaski County | 708 |
| Artemus | 16 | Knox County | 706 |
| Lynch | 17 | Harlan County | 595 |
| Loyall | 18 | Harlan County | 586 |
| Emlyn | 19 | Whitley County | 559 |
| Wallins Creek | 20 | Harlan County | 500 |
| Cawood | 21 | Harlan County | 492 |
| Kenvir | 22 | Harlan County | 485 |
| Coldiron | 23 | Harlan County | 469 |
| Benham | 24 | Harlan County | 458 |
| Ages | 25 | Harlan County | 401 |
| Rockholds | 26 | Whitley County | 366 |
| Pathfork | 27 | Harlan County | 283 |
| Coxton | 28 | Harlan County | 267 |
| Pleasant View | 29 | McCreary County | 236 |
| Arjay | 30 | Bell County | 112 |