23 cities
| City | Rank | County | 2025 Pop. ↓ |
|---|---|---|---|
| Keene | 1 | Cheshire County | 23,101 |
| Swanzey | 2 | Cheshire County | 7,489 |
| Rindge | 3 | Cheshire County | 6,591 |
| Jaffrey | 4 | Cheshire County | 5,607 |
| Winchester | 5 | Cheshire County | 4,270 |
| Hinsdale | 6 | Cheshire County | 4,047 |
| Walpole | 7 | Cheshire County | 3,738 |
| Chesterfield | 8 | Cheshire County | 3,674 |
| Fitzwilliam | 9 | Cheshire County | 2,515 |
| Marlborough | 10 | Cheshire County | 2,219 |
| Troy | 11 | Cheshire County | 2,209 |
| Alstead | 12 | Cheshire County | 1,940 |
| Westmoreland | 13 | Cheshire County | 1,744 |
| Dublin | 14 | Cheshire County | 1,609 |
| Stoddard | 15 | Cheshire County | 1,467 |
| Richmond | 16 | Cheshire County | 1,247 |
| Harrisville | 17 | Cheshire County | 1,006 |
| Surry | 18 | Cheshire County | 868 |
| Gilsum | 19 | Cheshire County | 788 |
| Marlow | 20 | Cheshire County | 787 |
| Sullivan | 21 | Cheshire County | 707 |
| Nelson | 22 | Cheshire County | 676 |
| Roxbury | 23 | Cheshire County | 225 |
Cheshire County is the county generally considered as Monadnock New Hampshire.