42 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Pittsfield | 1 | 42,588 | 43,807 | -0.57% | 1,052 | 40 | City |
| Pittsfield | 2 | 42,466 | 43,807 | -0.71% | 1,049 | 40 | City |
| North Adams | 3 | 12,353 | 12,751 | -0.52% | 607 | 20 | City |
| North Adams | 4 | 12,304 | 12,751 | -0.72% | 605 | 20 | City |
| Adams | 5 | 7,865 | 8,141 | -0.82% | 344 | 23 | Town |
| Williamstown | 6 | 7,347 | 7,518 | -0.26% | 157 | 47 | Town |
| Great Barrington | 7 | 7,130 | 7,181 | -0.45% | 159 | 45 | Town |
| Dalton | 8 | 6,110 | 6,319 | -0.73% | 281 | 22 | Town |
| Adams | 9 | 5,774 | 5,689 | 0.31% | 2,357 | 2 | CDP |
| Lee | 10 | 5,642 | 5,780 | -0.46% | 216 | 26 | Town |
| Lenox | 11 | 5,048 | 5,095 | -0.16% | 238 | 21 | Town |
| Williamstown | 12 | 4,541 | 4,565 | 0.31% | 1,336 | 3 | CDP |
| Sheffield | 13 | 3,279 | 3,326 | -0.58% | 69 | 47 | Town |
| Cheshire | 14 | 3,147 | 3,253 | -0.76% | 117 | 27 | Town |
| Lanesborough | 15 | 2,973 | 3,045 | -0.57% | 103 | 29 | Town |
| Lenox | 16 | 2,080 | 1,984 | 1.32% | 1,043 | 2 | CDP |
| Stockbridge | 17 | 1,974 | 2,013 | -0.5% | 87 | 23 | Town |
| Becket | 18 | 1,899 | 1,932 | -0.58% | 41 | 46 | Town |
| Hinsdale | 19 | 1,882 | 1,915 | -0.37% | 91 | 21 | Town |
| Great Barrington | 20 | 1,805 | 2,213 | -1.53% | 1,253 | 1 | CDP |
| Clarksburg | 21 | 1,628 | 1,655 | -0.37% | 128 | 13 | Town |
| Otis | 22 | 1,599 | 1,634 | -0.62% | 45 | 36 | Town |
| New Marlborough | 23 | 1,479 | 1,528 | -0.8% | 32 | 47 | Town |
| Richmond | 24 | 1,395 | 1,409 | -0.21% | 75 | 19 | Town |
| Lee | 25 | 1,371 | 1,508 | -3.18% | 1,035 | 1 | CDP |
| Egremont | 26 | 1,363 | 1,370 | -0.29% | 73 | 19 | Town |
| West Stockbridge | 27 | 1,311 | 1,340 | -0.53% | 71 | 18 | Town |
| Monterey | 28 | 1,068 | 1,092 | -0.56% | 40 | 26 | Town |
| Sandisfield | 29 | 977 | 985 | -0.2% | 19 | 52 | Town |
| Housatonic | 30 | 954 | 682 | -1.04% | 1,071 | 1 | CDP |
| Windsor | 31 | 807 | 825 | -0.49% | 23 | 35 | Town |
| Peru | 32 | 790 | 808 | -0.63% | 30 | 26 | Town |
| Hancock | 33 | 731 | 748 | -0.54% | 20 | 36 | Town |
| Florida | 34 | 661 | 691 | -1.05% | 27 | 24 | Town |
| Savoy | 35 | 647 | 646 | 0% | 18 | 36 | Town |
| Cheshire | 36 | 555 | 683 | 0.54% | 1,445 | 0 | CDP |
| Washington | 37 | 498 | 492 | 0.2% | 13 | 38 | Town |
| Alford | 38 | 477 | 486 | -0.42% | 41 | 12 | Town |
| Tyringham | 39 | 412 | 428 | -0.96% | 22 | 19 | Town |
| Lenox Dale | 40 | 319 | 337 | 7.05% | 583 | 1 | CDP |
| New Ashford | 41 | 247 | 246 | 0% | 18 | 13 | Town |
| Mount Washington | 42 | 155 | 160 | -0.64% | 7 | 22 | Town |
Pittsfield is the largest city in Berkshire County, with a population of 42,588.
Mount Washington is the smallest city in Berkshire County, with a population of 155.
There are 42 cities in Berkshire County, Massachusetts.