43 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Northampton | 1 | 31,824 | 29,567 | 1.63% | 929 | 34 | City |
| Northampton | 2 | 31,824 | 29,279 | 1.63% | 929 | 34 | City |
| Northampton | 3 | 31,246 | 29,567 | -0.22% | 912 | 34 | City |
| Northampton | 4 | 31,246 | 29,279 | -0.22% | 912 | 34 | City |
| South Hadley | 5 | 17,958 | 18,153 | -0.4% | 1,014 | 18 | Town |
| South Hadley | 6 | 17,958 | 16,306 | -0.4% | 1,014 | 18 | Town |
| Belchertown | 7 | 15,337 | 15,351 | -0.23% | 292 | 53 | Town |
| Belchertown | 8 | 15,337 | 15,339 | -0.23% | 292 | 53 | Town |
| Ware | 9 | 10,172 | 10,060 | 0.3% | 296 | 34 | Town |
| Ware | 10 | 10,172 | 10,037 | 0.3% | 296 | 34 | Town |
| Ware | 11 | 6,274 | 5,978 | 0.11% | 1,009 | 6 | CDP |
| Southampton | 12 | 6,139 | 6,228 | -0.68% | 218 | 28 | Town |
| Southampton | 13 | 6,139 | 6,221 | -0.68% | 218 | 28 | Town |
| Granby | 14 | 6,045 | 6,109 | -0.31% | 217 | 28 | Town |
| Granby | 15 | 6,045 | 6,099 | -0.31% | 217 | 28 | Town |
| Hadley | 16 | 5,265 | 5,325 | -0.36% | 228 | 23 | Town |
| Hadley | 17 | 5,265 | 5,317 | -0.36% | 228 | 23 | Town |
| Hatfield | 18 | 3,308 | 3,344 | -0.39% | 208 | 16 | Town |
| Hatfield | 19 | 3,308 | 3,338 | -0.39% | 208 | 16 | Town |
| Belchertown | 20 | 2,585 | 3,037 | -0.81% | 514 | 5 | CDP |
| Williamsburg | 21 | 2,470 | 2,504 | -0.2% | 97 | 26 | Town |
| Williamsburg | 22 | 2,470 | 2,500 | -0.2% | 97 | 26 | Town |
| Huntington | 23 | 2,062 | 2,100 | -0.43% | 78 | 26 | Town |
| Huntington | 24 | 2,062 | 2,095 | -0.43% | 78 | 26 | Town |
| Westhampton | 25 | 1,627 | 1,619 | -0.12% | 60 | 27 | Town |
| Westhampton | 26 | 1,627 | 1,615 | -0.12% | 60 | 27 | Town |
| Pelham | 27 | 1,414 | 1,284 | 5.29% | 56 | 25 | Town |
| Pelham | 28 | 1,414 | 1,281 | 5.29% | 56 | 25 | Town |
| Hatfield | 29 | 1,334 | 1,154 | 0.08% | 544 | 2 | CDP |
| Worthington | 30 | 1,177 | 1,193 | -0.34% | 37 | 32 | Town |
| Worthington | 31 | 1,177 | 1,192 | -0.34% | 37 | 32 | Town |
| Chesterfield | 32 | 1,169 | 1,187 | -0.43% | 38 | 31 | Town |
| Chesterfield | 33 | 1,169 | 1,186 | -0.43% | 38 | 31 | Town |
| Granby | 34 | 1,128 | 1,183 | -1.4% | 325 | 3 | CDP |
| Goshen | 35 | 936 | 962 | -0.64% | 54 | 17 | Town |
| Goshen | 36 | 936 | 960 | -0.64% | 54 | 17 | Town |
| Huntington | 37 | 847 | 675 | -0.7% | 183 | 5 | CDP |
| Cummington | 38 | 815 | 829 | -0.49% | 36 | 23 | Town |
| Cummington | 39 | 815 | 827 | -0.49% | 36 | 23 | Town |
| Plainfield | 40 | 660 | 630 | 1.69% | 31 | 21 | Town |
| Plainfield | 41 | 660 | 630 | 1.69% | 31 | 21 | Town |
| Middlefield | 42 | 400 | 388 | 0.76% | 17 | 24 | Town |
| Middlefield | 43 | 400 | 389 | 0.76% | 17 | 24 | Town |
Northampton is the largest city in Hampshire County, with a population of 31,824.
Middlefield is the smallest city in Hampshire County, with a population of 400.
There are 43 cities in Hampshire County, Massachusetts.