29 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Poughkeepsie | 1 | 45,690 | 45,165 | -0.02% | 1,601 | 29 | Town |
| Poughkeepsie | 2 | 32,655 | 31,568 | 0.56% | 6,347 | 5 | City |
| East Fishkill | 3 | 29,773 | 29,719 | 0.03% | 526 | 57 | Town |
| Wappinger | 4 | 28,266 | 28,204 | 0.07% | 1,044 | 27 | Town |
| Fishkill | 5 | 23,771 | 23,179 | 1.76% | 872 | 27 | Town |
| Hyde Park | 6 | 21,616 | 20,980 | 0.65% | 590 | 37 | Town |
| LaGrange | 7 | 16,963 | 15,980 | 0.99% | 425 | 40 | Town |
| Beacon | 8 | 15,776 | 14,323 | 1.56% | 3,329 | 5 | City |
| Beekman | 9 | 14,366 | 14,116 | 0.52% | 476 | 30 | Town |
| Red Hook | 10 | 11,282 | 10,947 | 0.37% | 312 | 36 | Town |
| Pleasant Valley | 11 | 9,835 | 9,796 | 0.14% | 302 | 33 | Town |
| Dover | 12 | 8,375 | 8,395 | 0.04% | 152 | 55 | Town |
| Pawling | 13 | 8,295 | 7,977 | 0.92% | 189 | 44 | Town |
| Rhinebeck | 14 | 7,666 | 7,581 | 0.37% | 215 | 36 | Town |
| Wappingers Falls | 15 | 6,053 | 6,104 | -0.13% | 5,400 | 1 | Village |
| Union Vale | 16 | 4,617 | 4,561 | 0.37% | 125 | 37 | Town |
| Washington | 17 | 4,520 | 4,498 | 0.24% | 78 | 58 | Town |
| Amenia | 18 | 4,083 | 3,768 | 1.39% | 94 | 43 | Town |
| Stanford | 19 | 3,722 | 3,679 | 0.3% | 75 | 50 | Town |
| North East | 20 | 2,999 | 2,970 | 0.17% | 69 | 43 | Town |
| Rhinebeck | 21 | 2,528 | 2,702 | -1.13% | 1,679 | 2 | Village |
| Milan | 22 | 2,343 | 2,255 | 0.77% | 65 | 36 | Town |
| Pine Plains | 23 | 2,315 | 2,218 | 0.26% | 76 | 31 | Town |
| Fishkill | 24 | 2,137 | 2,164 | -0.19% | 2,569 | 1 | Village |
| Pawling | 25 | 2,109 | 1,991 | 0.96% | 1,079 | 2 | Village |
| Red Hook | 26 | 1,947 | 1,973 | -0.21% | 1,845 | 1 | Village |
| Millbrook | 27 | 1,438 | 1,458 | -0.21% | 773 | 2 | Village |
| Tivoli | 28 | 1,016 | 1,024 | -0.1% | 659 | 2 | Village |
| Millerton | 29 | 883 | 892 | -0.11% | 1,433 | 1 | Village |
Poughkeepsie is the largest city in Dutchess County, with a population of 45,690.
Millerton is the smallest city in Dutchess County, with a population of 883.
There are 29 cities in Dutchess County, New York.