26 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Hartford | 1 | 10,499 | 10,694 | -0.75% | 233 | 45 | Town |
| Springfield | 2 | 8,964 | 9,066 | -0.36% | 182 | 49 | Town |
| Norwich | 3 | 3,601 | 3,614 | -0.36% | 81 | 44 | Town |
| Windsor | 4 | 3,470 | 3,548 | -0.74% | 179 | 19 | Town |
| Hartland | 5 | 3,379 | 3,449 | -0.91% | 75 | 45 | Town |
| Chester | 6 | 2,975 | 2,985 | -0.3% | 53 | 56 | Town |
| Woodstock | 7 | 2,968 | 3,005 | -0.67% | 67 | 44 | Town |
| Weathersfield | 8 | 2,792 | 2,838 | -0.75% | 64 | 44 | Town |
| Royalton | 9 | 2,699 | 2,748 | -0.88% | 67 | 40 | Town |
| Ludlow | 10 | 2,134 | 2,169 | -0.7% | 61 | 35 | Town |
| Bethel | 11 | 1,884 | 1,942 | -0.84% | 41 | 45 | Town |
| Sharon | 12 | 1,534 | 1,564 | -0.84% | 39 | 40 | Town |
| Cavendish | 13 | 1,372 | 1,395 | -0.87% | 35 | 39 | Town |
| West Windsor | 14 | 1,349 | 1,348 | -0.52% | 55 | 25 | Town |
| Rochester | 15 | 1,073 | 1,097 | -0.65% | 19 | 57 | Town |
| Barnard | 16 | 981 | 991 | -0.81% | 20 | 48 | Town |
| Pomfret | 17 | 964 | 913 | 0.42% | 24 | 39 | Town |
| Woodstock | 18 | 922 | 936 | -0.22% | 781 | 1 | Village |
| Bridgewater | 19 | 884 | 903 | -1.01% | 18 | 49 | Town |
| Ludlow | 20 | 779 | 784 | -0.13% | 582 | 1 | Village |
| Stockbridge | 21 | 722 | 715 | -0.41% | 16 | 46 | Town |
| Reading | 22 | 678 | 684 | -0.44% | 16 | 41 | Town |
| Plymouth | 23 | 656 | 638 | 0.46% | 14 | 48 | Town |
| Weston | 24 | 624 | 628 | -0.32% | 18 | 35 | Town |
| Andover | 25 | 563 | 571 | -1.05% | 20 | 29 | Town |
| Baltimore | 26 | 234 | 231 | 0% | 49 | 5 | Town |
Hartford is the largest city in Windsor County, with a population of 10,499.
Baltimore is the smallest city in Windsor County, with a population of 234.
There are 26 cities in Windsor County, Vermont.