| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Northampton | 1 | 30,767 | 29,299 | -0.9% | 898 | 34 | City |
| South Hadley | 2 | 17,638 | 16,305 | -0.73% | 996 | 18 | Town |
| Belchertown | 3 | 15,258 | 15,345 | -0.05% | 290 | 53 | Town |
| Ware | 4 | 10,187 | 10,037 | 0.58% | 296 | 34 | Town |
| Southampton | 5 | 6,030 | 6,221 | -0.9% | 214 | 28 | Town |
| Granby | 6 | 5,966 | 6,095 | -0.42% | 214 | 28 | Town |
| Hadley | 7 | 5,176 | 5,319 | -0.71% | 224 | 23 | Town |
| Hatfield | 8 | 3,272 | 3,338 | -0.43% | 206 | 16 | Town |
| Williamsburg | 9 | 2,434 | 2,500 | -0.45% | 95 | 26 | Town |
| Huntington | 10 | 2,023 | 2,093 | -0.78% | 77 | 26 | Town |
| Westhampton | 11 | 1,615 | 1,618 | -0.19% | 59 | 27 | Town |
| Pelham | 12 | 1,296 | 1,269 | -0.92% | 52 | 25 | Town |
| Worthington | 13 | 1,158 | 1,193 | -0.69% | 36 | 32 | Town |
| Chesterfield | 14 | 1,146 | 1,184 | -0.69% | 37 | 31 | Town |
| Goshen | 15 | 938 | 961 | -0.53% | 54 | 17 | Town |
| Cummington | 16 | 798 | 825 | -0.62% | 35 | 23 | Town |
| Plainfield | 17 | 642 | 630 | -0.16% | 30 | 21 | Town |
| Middlefield | 18 | 391 | 388 | -0.26% | 16 | 24 | Town |
Northampton is the largest city in Hampshire County, with a population of 30,767.
Middlefield is the smallest city in Hampshire County, with a population of 391.
There are 18 cities in Hampshire County, Massachusetts.