42 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Pittsfield | 1 | 42,588 | 43,807 | -0.57% | 1,052 | 40.47 | City |
| Pittsfield city | 2 | 42,466 | 43,807 | -0.71% | 1,049 | 40.47 | City |
| North Adams city | 3 | 12,353 | 12,751 | -0.52% | 607 | 20.35 | City |
| North Adams | 4 | 12,304 | 12,751 | -0.72% | 605 | 20.35 | City |
| Adams town | 5 | 7,865 | 8,141 | -0.82% | 344 | 22.89 | Town |
| Williamstown town | 6 | 7,347 | 7,518 | -0.26% | 157 | 46.73 | Town |
| Great Barrington town | 7 | 7,130 | 7,181 | -0.45% | 159 | 44.82 | Town |
| Dalton town | 8 | 6,110 | 6,319 | -0.73% | 281 | 21.77 | Town |
| Adams | 9 | 5,774 | 5,689 | 0.31% | 2,357 | 2.45 | CDP |
| Lee town | 10 | 5,642 | 5,780 | -0.46% | 216 | 26.15 | Town |
| Lenox town | 11 | 5,048 | 5,095 | -0.16% | 238 | 21.22 | Town |
| Williamstown | 12 | 4,541 | 4,565 | 0.31% | 1,336 | 3.40 | CDP |
| Sheffield town | 13 | 3,279 | 3,326 | -0.58% | 69 | 47.41 | Town |
| Cheshire town | 14 | 3,147 | 3,253 | -0.76% | 117 | 26.81 | Town |
| Lanesborough town | 15 | 2,973 | 3,045 | -0.57% | 103 | 28.85 | Town |
| Lenox | 16 | 2,080 | 1,984 | 1.32% | 1,043 | 2 | CDP |
| Stockbridge town | 17 | 1,974 | 2,013 | -0.5% | 87 | 22.74 | Town |
| Becket town | 18 | 1,899 | 1,932 | -0.58% | 41 | 46.06 | Town |
| Hinsdale town | 19 | 1,882 | 1,915 | -0.37% | 91 | 20.73 | Town |
| Great Barrington | 20 | 1,805 | 2,213 | -1.53% | 1,253 | 1.44 | CDP |
| Clarksburg town | 21 | 1,628 | 1,655 | -0.37% | 128 | 12.69 | Town |
| Otis town | 22 | 1,599 | 1,634 | -0.62% | 45 | 35.56 | Town |
| New Marlborough town | 23 | 1,479 | 1,528 | -0.8% | 32 | 46.88 | Town |
| Richmond town | 24 | 1,395 | 1,409 | -0.21% | 75 | 18.71 | Town |
| Lee | 25 | 1,371 | 1,508 | -3.18% | 1,035 | 1.32 | CDP |
| Egremont town | 26 | 1,363 | 1,370 | -0.29% | 73 | 18.67 | Town |
| West Stockbridge town | 27 | 1,311 | 1,340 | -0.53% | 71 | 18.45 | Town |
| Monterey town | 28 | 1,068 | 1,092 | -0.56% | 40 | 26.43 | Town |
| Sandisfield town | 29 | 977 | 985 | -0.2% | 19 | 51.80 | Town |
| Housatonic | 30 | 954 | 682 | -1.04% | 1,071 | 0.89 | CDP |
| Windsor town | 31 | 807 | 825 | -0.49% | 23 | 34.99 | Town |
| Peru town | 32 | 790 | 808 | -0.63% | 30 | 25.93 | Town |
| Hancock town | 33 | 731 | 748 | -0.54% | 20 | 35.68 | Town |
| Florida town | 34 | 661 | 691 | -1.05% | 27 | 24.36 | Town |
| Savoy town | 35 | 647 | 646 | 0% | 18 | 35.85 | Town |
| Cheshire | 36 | 555 | 683 | 0.54% | 1,445 | 0.38 | CDP |
| Washington town | 37 | 498 | 492 | 0.2% | 13 | 38 | Town |
| Alford town | 38 | 477 | 486 | -0.42% | 41 | 11.51 | Town |
| Tyringham town | 39 | 412 | 428 | -0.96% | 22 | 18.64 | Town |
| Lenox Dale | 40 | 319 | 337 | 7.05% | 583 | 0.55 | CDP |
| New Ashford town | 41 | 247 | 246 | 0% | 18 | 13.46 | Town |
| Mount Washington town | 42 | 155 | 160 | -0.64% | 7 | 22.25 | Town |
Pittsfield is the largest city in Berkshire County, with a population of 42,588.
Mount Washington town is the smallest city in Berkshire County.
There are 42 cities in Berkshire County, Massachusetts.