23 cities
| City | Rank | County | 2026 Pop. ↓ |
|---|---|---|---|
| Keene | 1 | Cheshire County | 23,166 |
| Swanzey | 2 | Cheshire County | 7,515 |
| Rindge | 3 | Cheshire County | 6,639 |
| Jaffrey | 4 | Cheshire County | 5,665 |
| Winchester | 5 | Cheshire County | 4,285 |
| Hinsdale | 6 | Cheshire County | 4,067 |
| Walpole | 7 | Cheshire County | 3,759 |
| Chesterfield | 8 | Cheshire County | 3,688 |
| Fitzwilliam | 9 | Cheshire County | 2,547 |
| Marlborough | 10 | Cheshire County | 2,245 |
| Troy | 11 | Cheshire County | 2,220 |
| Alstead | 12 | Cheshire County | 1,955 |
| Westmoreland | 13 | Cheshire County | 1,751 |
| Dublin | 14 | Cheshire County | 1,625 |
| Stoddard | 15 | Cheshire County | 1,485 |
| Richmond | 16 | Cheshire County | 1,255 |
| Harrisville | 17 | Cheshire County | 1,009 |
| Surry | 18 | Cheshire County | 875 |
| Marlow | 19 | Cheshire County | 800 |
| Gilsum | 20 | Cheshire County | 790 |
| Sullivan | 21 | Cheshire County | 719 |
| Nelson | 22 | Cheshire County | 685 |
| Roxbury | 23 | Cheshire County | 225 |
Cheshire County is the county generally considered as Monadnock New Hampshire.