Note: As defined by the US Census Bureau, a city's official boundaries often extend miles beyond the city itself and may even cross county lines. As such, several thousand US cities officially exist in two or more counties (and therefore appear on multiple counties' lists of cities.)
City | Rank | 2024 Pop. | 2020 Pop. | Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Pittsfield | 1 | 42,771 | 43,807 | -0.71% | 1,057 | 40.5 | City |
| North Adams | 2 | 12,418 | 12,751 | -0.52% | 610 | 20.3 | City |
| Adams | 3 | 7,930 | 8,141 | -0.81% | 346 | 22.9 | Town |
| Williamstown | 4 | 7,366 | 7,518 | -0.26% | 158 | 46.7 | Town |
| Great Barrington | 5 | 7,162 | 7,181 | -0.45% | 160 | 44.8 | Town |
| Dalton | 6 | 6,155 | 6,319 | -0.73% | 283 | 21.8 | Town |
| Lee | 7 | 5,668 | 5,780 | -0.46% | 217 | 26.1 | Town |
| Lenox | 8 | 5,056 | 5,095 | -0.16% | 238 | 21.2 | Town |
| Sheffield | 9 | 3,298 | 3,326 | -0.57% | 70 | 47.4 | Town |
| Cheshire | 10 | 3,171 | 3,253 | -0.75% | 118 | 26.8 | Town |
| Lanesborough | 11 | 2,990 | 3,045 | -0.56% | 104 | 28.9 | Town |
| Stockbridge | 12 | 1,984 | 2,013 | -0.5% | 87 | 22.7 | Town |
| Becket | 13 | 1,910 | 1,932 | -0.57% | 41 | 46.1 | Town |
| Hinsdale | 14 | 1,889 | 1,915 | -0.37% | 91 | 20.7 | Town |
| Clarksburg | 15 | 1,634 | 1,655 | -0.37% | 129 | 12.7 | Town |
| Otis | 16 | 1,609 | 1,634 | -0.62% | 45 | 35.6 | Town |
| New Marlborough | 17 | 1,491 | 1,528 | -0.8% | 32 | 46.9 | Town |
| Richmond | 18 | 1,398 | 1,409 | -0.21% | 75 | 18.7 | Town |
| Egremont | 19 | 1,367 | 1,370 | -0.29% | 73 | 18.7 | Town |
| West Stockbridge | 20 | 1,318 | 1,340 | -0.53% | 71 | 18.5 | Town |
| Monterey | 21 | 1,074 | 1,092 | -0.56% | 41 | 26.4 | Town |
Note: City markers shown outside the county boundary mean that a part of the city extends into this county, but is primarily located in an adjacent county.
Pittsfield is the largest city in Berkshire County.
Monterey is the smallest city in Berkshire County.
There are 21 cities in Berkshire County, Massachusetts.