34 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Pittsfield | 1 | 43,049 | 43,836 | -0.17% | 1,064 | 40 | City |
| Pittsfield | 2 | 42,942 | 43,836 | -0.42% | 1,061 | 40 | City |
| North Adams | 3 | 12,467 | 12,754 | -0.2% | 613 | 20 | City |
| North Adams | 4 | 12,426 | 12,754 | -0.53% | 611 | 20 | City |
| Williamstown | 5 | 9,185 | 8,717 | -0.04% | 197 | 47 | Town |
| Adams | 6 | 7,968 | 8,146 | -0.3% | 348 | 23 | Town |
| Great Barrington | 7 | 7,287 | 7,174 | 0.58% | 163 | 45 | Town |
| Dalton | 8 | 6,180 | 6,325 | -0.29% | 284 | 22 | Town |
| Lee | 9 | 5,663 | 5,777 | -0.33% | 217 | 26 | Town |
| Lenox | 10 | 5,072 | 5,091 | 0% | 239 | 21 | Town |
| Sheffield | 11 | 3,326 | 3,324 | 0.06% | 70 | 47 | Town |
| Cheshire | 12 | 3,183 | 3,253 | -0.22% | 119 | 27 | Town |
| Lanesborough | 13 | 2,999 | 3,038 | -0.17% | 104 | 29 | Town |
| Stockbridge | 14 | 1,988 | 1,999 | 0.1% | 87 | 23 | Town |
| Becket | 15 | 1,921 | 1,931 | -0.05% | 42 | 46 | Town |
| Hinsdale | 16 | 1,891 | 1,906 | 0.05% | 91 | 21 | Town |
| Clarksburg | 17 | 1,632 | 1,656 | -0.31% | 129 | 13 | Town |
| Otis | 18 | 1,616 | 1,634 | -0.19% | 45 | 36 | Town |
| New Marlborough | 19 | 1,498 | 1,528 | -0.33% | 32 | 47 | Town |
| Richmond | 20 | 1,404 | 1,411 | -0.07% | 75 | 19 | Town |
| Egremont | 21 | 1,377 | 1,371 | 0.15% | 74 | 19 | Town |
| West Stockbridge | 22 | 1,322 | 1,336 | -0.08% | 72 | 18 | Town |
| Monterey | 23 | 1,088 | 1,090 | 0.28% | 41 | 26 | Town |
| Sandisfield | 24 | 984 | 986 | 0% | 19 | 52 | Town |
| Windsor | 25 | 818 | 825 | 0.12% | 23 | 35 | Town |
| Peru | 26 | 796 | 808 | -0.25% | 31 | 26 | Town |
| Hancock | 27 | 740 | 747 | 0% | 21 | 36 | Town |
| Florida | 28 | 671 | 690 | -0.3% | 28 | 24 | Town |
| Savoy | 29 | 662 | 645 | 1.07% | 18 | 36 | Town |
| Washington | 30 | 497 | 492 | 0% | 13 | 38 | Town |
| Alford | 31 | 482 | 488 | -0.21% | 42 | 12 | Town |
| Tyringham | 32 | 418 | 426 | -0.24% | 22 | 19 | Town |
| New Ashford | 33 | 248 | 248 | -0.4% | 18 | 13 | Town |
| Mount Washington | 34 | 157 | 160 | 0% | 7 | 22 | Town |
Pittsfield is the largest city in Berkshire County, with a population of 43,049.
Mount Washington is the smallest city in Berkshire County, with a population of 157.
There are 34 cities in Berkshire County, Massachusetts.