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 |
|---|---|---|---|---|---|---|---|
| Poughkeepsie | 1 | 45,453 | 45,179 | -0.14% | 1,593 | 28.5 | Town |
| Poughkeepsie | 2 | 31,841 | 31,564 | 0.22% | 6,189 | 5.1 | City |
| East Fishkill | 3 | 29,506 | 29,715 | -0.43% | 522 | 56.6 | Town |
| Wappinger | 4 | 27,965 | 28,205 | -0.53% | 1,033 | 27.1 | Town |
| Fishkill | 5 | 22,365 | 23,184 | -0.44% | 820 | 27.3 | Town |
| Hyde Park | 6 | 21,169 | 20,962 | 0.21% | 578 | 36.6 | Town |
| LaGrange | 7 | 16,387 | 15,978 | -0.11% | 411 | 39.9 | Town |
| Beacon | 8 | 15,259 | 14,322 | 1.56% | 3,220 | 4.7 | City |
| Beekman | 9 | 14,169 | 14,114 | 0.47% | 469 | 30.2 | Town |
| Red Hook | 10 | 11,118 | 10,942 | 0.04% | 308 | 36.1 | Town |
| Pleasant Valley | 11 | 9,731 | 9,792 | -0.25% | 299 | 32.6 | Town |
| Dover | 12 | 8,291 | 8,394 | -0.55% | 150 | 55.2 | Town |
| Pawling | 13 | 8,070 | 7,978 | 0.39% | 184 | 44.0 | Town |
| Rhinebeck | 14 | 7,468 | 7,586 | -1.19% | 209 | 35.7 | Town |
| Wappingers Falls | 15 | 6,027 | 6,103 | -0.31% | 5,376 | 1.1 | Village |
| Union Vale | 16 | 4,539 | 4,567 | -0.37% | 123 | 37.0 | Town |
| Washington | 17 | 4,453 | 4,495 | -0.38% | 77 | 58.0 | Town |
| Amenia | 18 | 3,978 | 3,769 | 1.87% | 92 | 43.3 | Town |
| Stanford | 19 | 3,657 | 3,675 | -0.3% | 74 | 49.6 | Town |
| North East | 20 | 2,969 | 2,972 | -0.1% | 69 | 43.2 | Town |
| Rhinebeck | 21 | 2,543 | 2,707 | -1.59% | 1,689 | 1.5 | Village |
| Pine Plains | 22 | 2,341 | 2,218 | 2.27% | 77 | 30.6 | Town |
| Milan | 23 | 2,282 | 2,254 | 0.13% | 63 | 36.1 | Town |
| Fishkill | 24 | 2,133 | 2,164 | -0.37% | 2,564 | 0.8 | Village |
| Pawling | 25 | 2,023 | 1,991 | 0.4% | 1,035 | 2.0 | Village |
| Red Hook | 26 | 1,941 | 1,972 | -0.41% | 1,840 | 1.1 | Village |
| Millbrook | 27 | 1,436 | 1,458 | -0.42% | 772 | 1.9 | Village |
| Tivoli | 28 | 1,009 | 1,021 | -0.3% | 654 | 1.5 | Village |
| Millerton | 29 | 877 | 889 | -0.34% | 1,424 | 0.6 | 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.
Poughkeepsie is the largest city in Dutchess County.
Millerton is the smallest city in Dutchess County.
There are 29 cities in Dutchess County, New York.