| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Pittsfield | 1 | 42,555 | 43,837 | -0.83% | 1,052 | 40 | City |
| North Adams | 2 | 12,279 | 12,732 | -0.72% | 603 | 20 | City |
| Williamstown | 3 | 9,145 | 8,719 | -0.45% | 196 | 47 | Town |
| Adams | 4 | 7,866 | 8,145 | -0.86% | 344 | 23 | Town |
| Great Barrington | 5 | 7,218 | 7,174 | -0.29% | 161 | 45 | Town |
| Dalton | 6 | 6,111 | 6,325 | -0.75% | 281 | 22 | Town |
| Lee | 7 | 5,649 | 5,770 | -0.42% | 216 | 26 | Town |
| Lenox | 8 | 5,037 | 5,088 | -0.43% | 237 | 21 | Town |
| Sheffield | 9 | 3,301 | 3,319 | -0.39% | 70 | 47 | Town |
| Cheshire | 10 | 3,157 | 3,249 | -0.72% | 118 | 27 | Town |
| Lanesborough | 11 | 2,979 | 3,045 | -0.67% | 103 | 29 | Town |
| Stockbridge | 12 | 1,974 | 1,998 | -0.4% | 87 | 23 | Town |
| Becket | 13 | 1,912 | 1,937 | -0.52% | 42 | 46 | Town |
| Hinsdale | 14 | 1,869 | 1,902 | -0.59% | 90 | 21 | Town |
| Clarksburg | 15 | 1,619 | 1,646 | -0.37% | 128 | 13 | Town |
| Otis | 16 | 1,598 | 1,632 | -0.75% | 45 | 36 | Town |
| New Marlborough | 17 | 1,490 | 1,531 | -0.67% | 32 | 47 | Town |
| Richmond | 18 | 1,394 | 1,410 | -0.43% | 75 | 19 | Town |
| Egremont | 19 | 1,367 | 1,365 | -0.15% | 73 | 19 | Town |
| West Stockbridge | 20 | 1,310 | 1,338 | -0.68% | 71 | 18 | Town |
| Monterey | 21 | 1,091 | 1,097 | -0.18% | 41 | 26 | Town |
| Sandisfield | 22 | 981 | 985 | -0.2% | 19 | 52 | Town |
| Windsor | 23 | 817 | 823 | 0% | 23 | 35 | Town |
| Peru | 24 | 783 | 810 | -1.01% | 30 | 26 | Town |
| Hancock | 25 | 744 | 751 | -0.53% | 21 | 36 | Town |
| Florida | 26 | 694 | 719 | -0.86% | 28 | 24 | Town |
| Savoy | 27 | 651 | 647 | -0.61% | 18 | 36 | Town |
| Washington | 28 | 504 | 495 | 0.4% | 13 | 38 | Town |
| Alford | 29 | 484 | 495 | -0.82% | 42 | 12 | Town |
| Tyringham | 30 | 422 | 427 | 0% | 23 | 19 | Town |
| New Ashford | 31 | 245 | 246 | -0.41% | 18 | 13 | Town |
| Mount Washington | 32 | 153 | 159 | -0.65% | 7.0 | 22 | Town |
Pittsfield is the largest city in Berkshire County, with a population of 42,555.
Mount Washington is the smallest city in Berkshire County, with a population of 153.
There are 32 cities in Berkshire County, Massachusetts.