| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Poughkeepsie | 1 | 46,259 | 45,529 | 0.59% | 1,621 | 29 | Town |
| Poughkeepsie | 2 | 32,668 | 31,571 | 0.52% | 6,349 | 5 | City |
| East Fishkill | 3 | 29,865 | 29,716 | 0.21% | 528 | 57 | Town |
| Wappinger | 4 | 28,226 | 28,199 | 0.04% | 1,043 | 27 | Town |
| Fishkill | 5 | 22,942 | 23,191 | 0.02% | 842 | 27 | Town |
| Hyde Park | 6 | 21,481 | 20,939 | 0.41% | 586 | 37 | Town |
| LaGrange | 7 | 16,750 | 15,985 | 0.37% | 420 | 40 | Town |
| Beacon | 8 | 15,064 | 14,329 | 0.89% | 3,179 | 5 | City |
| Beekman | 9 | 14,521 | 14,116 | 1.14% | 481 | 30 | Town |
| Red Hook | 10 | 11,180 | 11,017 | 0.46% | 309 | 36 | Town |
| Pleasant Valley | 11 | 9,834 | 9,791 | 0.12% | 302 | 33 | Town |
| Pawling | 12 | 8,507 | 7,969 | 2.3% | 193 | 44 | Town |
| Dover | 13 | 8,431 | 8,396 | 0.14% | 153 | 55 | Town |
| Rhinebeck | 14 | 7,714 | 7,578 | 0.73% | 216 | 36 | Town |
| Wappingers Falls | 15 | 6,035 | 6,101 | -0.21% | 5,384 | 1 | Village |
| Union Vale | 16 | 4,605 | 4,555 | 0.33% | 124 | 37 | Town |
| Washington | 17 | 4,509 | 4,501 | 0.16% | 78 | 58 | Town |
| Amenia | 18 | 4,126 | 3,766 | 1.83% | 95 | 43 | Town |
| Stanford | 19 | 3,713 | 3,678 | 0.27% | 75 | 50 | Town |
| North East | 20 | 2,990 | 2,972 | 0% | 69 | 43 | Town |
| Rhinebeck | 21 | 2,558 | 2,700 | -1.16% | 1,699 | 2 | Village |
| Milan | 22 | 2,350 | 2,257 | 0.95% | 65 | 36 | Town |
| Pine Plains | 23 | 2,316 | 2,218 | 0.39% | 76 | 31 | Town |
| Fishkill | 24 | 2,142 | 2,166 | -0.23% | 2,575 | 1 | Village |
| Pawling | 25 | 2,088 | 1,998 | 0.87% | 1,069 | 2 | Village |
| Red Hook | 26 | 1,951 | 1,974 | -0.26% | 1,849 | 1 | Village |
| Millbrook | 27 | 1,438 | 1,457 | -0.28% | 773 | 2 | Village |
| Tivoli | 28 | 1,017 | 1,026 | -0.2% | 660 | 2 | Village |
| Millerton | 29 | 878 | 890 | -0.23% | 1,425 | 1 | Village |
Poughkeepsie is the largest city in Dutchess County, with a population of 46,259.
Millerton is the smallest city in Dutchess County, with a population of 878.
There are 29 cities in Dutchess County, New York.