Note: As defined by the US Census Bureau, a city's official boundaries often extend miles beyond the city itself and may even cross county lines. As such, several thousand US cities officially exist in two or more counties (and therefore appear on multiple counties' lists of cities.)
City | Rank | 2024 Pop. | 2020 Pop. | Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Hartford | 1 | 10,718 | 10,695 | -0.23% | 238 | 45.1 | Town |
| Springfield | 2 | 9,038 | 9,065 | -0.34% | 184 | 49.2 | Town |
| Norwich | 3 | 3,639 | 3,614 | -0.11% | 82 | 44.5 | Town |
| Windsor | 4 | 3,538 | 3,550 | -0.34% | 182 | 19.4 | Town |
| Hartland | 5 | 3,491 | 3,450 | 0.2% | 77 | 45.2 | Town |
| Woodstock | 6 | 3,026 | 3,007 | -0.2% | 69 | 44.1 | Town |
| Chester | 7 | 3,008 | 2,985 | 0% | 54 | 55.7 | Town |
| Weathersfield | 8 | 2,847 | 2,836 | -0.21% | 65 | 43.5 | Town |
| Royalton | 9 | 2,774 | 2,747 | 0.14% | 69 | 40.4 | Town |
| Ludlow | 10 | 2,180 | 2,170 | -0.14% | 63 | 34.8 | Town |
| Bethel | 11 | 1,929 | 1,942 | -0.36% | 42 | 45.5 | Town |
| Sharon | 12 | 1,569 | 1,562 | -0.06% | 39 | 39.8 | Town |
| Cavendish | 13 | 1,406 | 1,390 | 0.14% | 36 | 39.4 | Town |
| West Windsor | 14 | 1,378 | 1,350 | 0.36% | 56 | 24.7 | Town |
| Rochester | 15 | 1,089 | 1,097 | -0.46% | 19 | 56.8 | Town |
| Barnard | 16 | 1,014 | 0 | 0.6% | 21 | 48.0 | Town |
| Woodstock | 17 | 937 | 936 | 0% | 794 | 1.2 | Village |
| Ludlow | 18 | 790 | 784 | 0.13% | 590 | 1.3 | Village |
Note: City markers shown outside the county boundary mean that a part of the city extends into this county, but is primarily located in an adjacent county.
Hartford is the largest city in Windsor County.
Ludlow is the smallest city in Windsor County.
There are 18 cities in Windsor County, Vermont.