23 cities
| City | Rank | County | 2025 Pop. ↓ |
|---|---|---|---|
| Keene city | 1 | Cheshire County | 22,893 |
| Swanzey town | 2 | Cheshire County | 7,432 |
| Rindge town | 3 | Cheshire County | 6,795 |
| Jaffrey town | 4 | Cheshire County | 5,553 |
| Winchester town | 5 | Cheshire County | 4,268 |
| Hinsdale town | 6 | Cheshire County | 3,998 |
| Walpole town | 7 | Cheshire County | 3,692 |
| Chesterfield town | 8 | Cheshire County | 3,685 |
| Fitzwilliam town | 9 | Cheshire County | 2,478 |
| Troy town | 10 | Cheshire County | 2,202 |
| Marlborough town | 11 | Cheshire County | 2,201 |
| Alstead town | 12 | Cheshire County | 1,926 |
| Westmoreland town | 13 | Cheshire County | 1,742 |
| Dublin town | 14 | Cheshire County | 1,594 |
| Stoddard town | 15 | Cheshire County | 1,461 |
| Richmond town | 16 | Cheshire County | 1,245 |
| Harrisville town | 17 | Cheshire County | 1,002 |
| Surry town | 18 | Cheshire County | 856 |
| Gilsum town | 19 | Cheshire County | 802 |
| Marlow town | 20 | Cheshire County | 755 |
| Sullivan town | 21 | Cheshire County | 702 |
| Nelson town | 22 | Cheshire County | 679 |
| Roxbury town | 23 | Cheshire County | 222 |
Cheshire County is the county generally considered as Monadnock New Hampshire.