72 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Hartford | 1 | 10,578 | 10,686 | -0.74% | 234 | 45 | Town |
| Hartford | 2 | 10,578 | 10,694 | -0.74% | 234 | 45 | Town |
| Springfield | 3 | 8,996 | 9,071 | -0.35% | 183 | 49 | Town |
| Springfield | 4 | 8,996 | 9,066 | -0.35% | 183 | 49 | Town |
| Wilder | 5 | 4,120 | 3,146 | 4.09% | 1,619 | 3 | CDP |
| Springfield | 6 | 3,938 | 4,028 | -0.05% | 1,178 | 3 | CDP |
| Norwich | 7 | 3,614 | 3,614 | -0.36% | 81 | 44 | Town |
| Norwich | 8 | 3,614 | 3,614 | -0.36% | 81 | 44 | Town |
| Windsor | 9 | 3,496 | 3,552 | -0.74% | 180 | 19 | Town |
| Windsor | 10 | 3,496 | 3,548 | -0.74% | 180 | 19 | Town |
| Hartland | 11 | 3,410 | 3,447 | -0.9% | 75 | 45 | Town |
| Hartland | 12 | 3,410 | 3,449 | -0.9% | 75 | 45 | Town |
| Woodstock | 13 | 2,988 | 3,005 | -0.66% | 68 | 44 | Town |
| Woodstock | 14 | 2,988 | 3,005 | -0.66% | 68 | 44 | Town |
| Chester | 15 | 2,984 | 2,985 | -0.3% | 54 | 56 | Town |
| Chester | 16 | 2,984 | 2,985 | -0.3% | 54 | 56 | Town |
| White River Junction | 17 | 2,886 | 2,528 | 1.41% | 1,235 | 2 | CDP |
| Weathersfield | 18 | 2,813 | 2,838 | -0.74% | 65 | 44 | Town |
| Weathersfield | 19 | 2,813 | 2,838 | -0.74% | 65 | 44 | Town |
| Royalton | 20 | 2,723 | 2,746 | -0.87% | 67 | 40 | Town |
| Royalton | 21 | 2,723 | 2,748 | -0.87% | 67 | 40 | Town |
| Windsor | 22 | 2,156 | 2,042 | 0.28% | 1,750 | 1 | CDP |
| Ludlow | 23 | 2,149 | 2,170 | -0.69% | 62 | 35 | Town |
| Ludlow | 24 | 2,149 | 2,169 | -0.69% | 62 | 35 | Town |
| Bethel | 25 | 1,900 | 1,943 | -0.84% | 42 | 45 | Town |
| Bethel | 26 | 1,900 | 1,942 | -0.84% | 42 | 45 | Town |
| Sharon | 27 | 1,547 | 1,563 | -0.83% | 39 | 40 | Town |
| Sharon | 28 | 1,547 | 1,564 | -0.83% | 39 | 40 | Town |
| Cavendish | 29 | 1,384 | 1,394 | -0.86% | 35 | 39 | Town |
| Cavendish | 30 | 1,384 | 1,395 | -0.86% | 35 | 39 | Town |
| West Windsor | 31 | 1,356 | 1,349 | -0.51% | 55 | 25 | Town |
| West Windsor | 32 | 1,356 | 1,348 | -0.51% | 55 | 25 | Town |
| Chester | 33 | 1,120 | 1,023 | 0.72% | 682 | 2 | CDP |
| Rochester | 34 | 1,080 | 1,098 | -0.64% | 19 | 57 | Town |
| Rochester | 35 | 1,080 | 1,097 | -0.64% | 19 | 57 | Town |
| Barnard | 36 | 989 | 990 | -0.8% | 21 | 48 | Town |
| Barnard | 37 | 989 | 991 | -0.8% | 21 | 48 | Town |
| Pomfret | 38 | 960 | 914 | 0.42% | 24 | 39 | Town |
| Pomfret | 39 | 960 | 913 | 0.42% | 24 | 39 | Town |
| Woodstock | 40 | 924 | 936 | -0.32% | 783 | 1 | Village |
| Woodstock | 41 | 924 | 936 | -0.32% | 783 | 1 | Village |
| Bridgewater | 42 | 893 | 902 | -1% | 18 | 49 | Town |
| Bridgewater | 43 | 893 | 903 | -1% | 18 | 49 | Town |
| Norwich | 44 | 829 | 621 | -0.36% | 571 | 1 | CDP |
| Ludlow | 45 | 780 | 784 | -0.13% | 583 | 1 | Village |
| Ludlow | 46 | 780 | 784 | -0.13% | 583 | 1 | Village |
| Stockbridge | 47 | 725 | 715 | -0.41% | 16 | 46 | Town |
| Stockbridge | 48 | 725 | 715 | -0.41% | 16 | 46 | Town |
| Bethel | 49 | 690 | 891 | 1.17% | 362 | 2 | CDP |
| Hartland | 50 | 686 | 537 | 3% | 631 | 1 | CDP |
| Reading | 51 | 681 | 684 | -0.44% | 17 | 41 | Town |
| Reading | 52 | 681 | 684 | -0.44% | 17 | 41 | Town |
| Plymouth | 53 | 653 | 638 | 0.46% | 14 | 48 | Town |
| Plymouth | 54 | 653 | 638 | 0.46% | 14 | 48 | Town |
| Weston | 55 | 626 | 628 | -0.32% | 18 | 35 | Town |
| Weston | 56 | 626 | 628 | -0.32% | 18 | 35 | Town |
| Hartford Village | 57 | 599 | 334 | 7.16% | 512 | 1 | CDP |
| Andover | 58 | 569 | 570 | -1.04% | 20 | 29 | Town |
| Andover | 59 | 569 | 571 | -1.04% | 20 | 29 | Town |
| West Woodstock | 60 | 496 | 164 | 7.13% | 593 | 1 | CDP |
| North Hartland | 61 | 444 | 274 | 2.07% | 443 | 1 | CDP |
| South Royalton | 62 | 420 | 609 | -4.11% | 378 | 1 | CDP |
| North Springfield | 63 | 416 | 740 | -2.35% | 338 | 1 | CDP |
| Ascutney | 64 | 401 | 380 | -2.2% | 238 | 2 | CDP |
| Proctorsville | 65 | 335 | 287 | -2.33% | 412 | 1 | CDP |
| Rochester | 66 | 295 | 247 | -0.34% | 465 | 1 | CDP |
| Quechee | 67 | 261 | 369 | -9.06% | 141 | 2 | CDP |
| Baltimore | 68 | 234 | 231 | 0% | 49 | 5 | Town |
| Baltimore | 69 | 234 | 231 | 0% | 49 | 5 | Town |
| Cavendish | 70 | 215 | 184 | 0.94% | 256 | 1 | CDP |
| Weston | 71 | 49 | 33 | 6.52% | 263 | 0 | CDP |
| South Woodstock | 72 | 30 | 107 | 7.14% | 33 | 1 | CDP |
Hartford is the largest city in Windsor County, with a population of 10,578.
South Woodstock is the smallest city in Windsor County, with a population of 30.
There are 72 cities in Windsor County, Vermont.