| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Hartford | 1 | 11,204 | 10,692 | 2.69% | 248 | 45 | Town |
| Springfield | 2 | 8,781 | 9,066 | -1.13% | 178 | 49 | Town |
| Norwich | 3 | 3,533 | 3,614 | -1.23% | 79 | 44 | Town |
| Windsor | 4 | 3,426 | 3,544 | -1.1% | 177 | 19 | Town |
| Hartland | 5 | 3,354 | 3,450 | -1.29% | 74 | 45 | Town |
| Woodstock | 6 | 2,944 | 3,003 | -0.88% | 67 | 44 | Town |
| Chester | 7 | 2,928 | 2,982 | -0.91% | 53 | 56 | Town |
| Weathersfield | 8 | 2,775 | 2,848 | -1.21% | 64 | 44 | Town |
| Royalton | 9 | 2,656 | 2,739 | -1.34% | 66 | 40 | Town |
| Ludlow | 10 | 2,114 | 2,167 | -0.94% | 61 | 35 | Town |
| Bethel | 11 | 1,863 | 1,940 | -1.27% | 41 | 45 | Town |
| Sharon | 12 | 1,523 | 1,563 | -1.23% | 38 | 40 | Town |
| Cavendish | 13 | 1,355 | 1,394 | -1.31% | 34 | 39 | Town |
| West Windsor | 14 | 1,349 | 1,353 | -0.44% | 55 | 25 | Town |
| Rochester | 15 | 1,064 | 1,097 | -0.84% | 19 | 57 | Town |
| Barnard | 16 | 992 | 1,004 | -0.8% | 21 | 48 | Town |
| Pomfret | 17 | 931 | 911 | -0.96% | 24 | 39 | Town |
| Woodstock | 18 | 899 | 928 | -0.44% | 762 | 1 | Village |
| Bridgewater | 19 | 878 | 908 | -1.46% | 18 | 49 | Town |
| Ludlow | 20 | 765 | 780 | -0.26% | 572 | 1 | Village |
| Stockbridge | 21 | 719 | 714 | -0.55% | 16 | 46 | Town |
| Reading | 22 | 661 | 676 | -0.9% | 16 | 41 | Town |
| Plymouth | 23 | 652 | 637 | 0.46% | 14 | 48 | Town |
| Weston | 24 | 629 | 629 | 0.16% | 18 | 35 | Town |
| Andover | 25 | 556 | 567 | -1.24% | 19 | 29 | Town |
| Baltimore | 26 | 229 | 229 | -0.43% | 48 | 5 | Town |
Hartford is the largest city in Windsor County, with a population of 11,204.
Baltimore is the smallest city in Windsor County, with a population of 229.
There are 26 cities in Windsor County, Vermont.