29 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Poughkeepsie | 1 | 45,699 | 45,165 | -0.02% | 1,601 | 29 | Town |
| Poughkeepsie | 2 | 32,474 | 31,568 | 0.56% | 6,312 | 5 | City |
| East Fishkill | 3 | 29,764 | 29,719 | 0.03% | 526 | 57 | Town |
| Wappinger | 4 | 28,247 | 28,204 | 0.07% | 1,043 | 27 | Town |
| Fishkill | 5 | 23,359 | 23,179 | 1.8% | 857 | 27 | Town |
| Hyde Park | 6 | 21,477 | 20,980 | 0.65% | 586 | 37 | Town |
| LaGrange | 7 | 16,796 | 15,980 | 1% | 421 | 40 | Town |
| Beacon | 8 | 15,534 | 14,323 | 1.58% | 3,278 | 5 | City |
| Beekman | 9 | 14,292 | 14,116 | 0.52% | 473 | 30 | Town |
| Red Hook | 10 | 11,240 | 10,947 | 0.38% | 311 | 36 | Town |
| Pleasant Valley | 11 | 9,821 | 9,796 | 0.14% | 301 | 33 | Town |
| Dover | 12 | 8,372 | 8,395 | 0.04% | 152 | 55 | Town |
| Pawling | 13 | 8,219 | 7,977 | 0.93% | 187 | 44 | Town |
| Rhinebeck | 14 | 7,638 | 7,581 | 0.37% | 214 | 36 | Town |
| Wappingers Falls | 15 | 6,061 | 6,104 | -0.15% | 5,407 | 1 | Village |
| Union Vale | 16 | 4,600 | 4,561 | 0.37% | 124 | 37 | Town |
| Washington | 17 | 4,509 | 4,498 | 0.24% | 78 | 58 | Town |
| Amenia | 18 | 4,027 | 3,768 | 1.41% | 93 | 43 | Town |
| Stanford | 19 | 3,711 | 3,679 | 0.3% | 75 | 50 | Town |
| North East | 20 | 2,994 | 2,970 | 0.17% | 69 | 43 | Town |
| Rhinebeck | 21 | 2,557 | 2,702 | -1.12% | 1,698 | 2 | Village |
| Milan | 22 | 2,325 | 2,255 | 0.78% | 64 | 36 | Town |
| Pine Plains | 23 | 2,309 | 2,218 | 0.26% | 75 | 31 | Town |
| Fishkill | 24 | 2,141 | 2,164 | -0.23% | 2,573 | 1 | Village |
| Pawling | 25 | 2,089 | 1,991 | 0.92% | 1,069 | 2 | Village |
| Red Hook | 26 | 1,951 | 1,973 | -0.26% | 1,849 | 1 | Village |
| Millbrook | 27 | 1,441 | 1,458 | -0.28% | 775 | 2 | Village |
| Tivoli | 28 | 1,017 | 1,024 | -0.2% | 660 | 2 | Village |
| Millerton | 29 | 884 | 892 | -0.23% | 1,435 | 1 | Village |
Poughkeepsie is the largest city in Dutchess County, with a population of 45,699.
Millerton is the smallest city in Dutchess County, with a population of 884.
There are 29 cities in Dutchess County, New York.