27 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Stamford | 1 | 140,049 | 135,474 | 0.66% | 3,722 | 38 | City |
| Norwalk | 2 | 94,352 | 90,897 | 0.74% | 4,123 | 23 | City |
| Danbury | 3 | 89,341 | 86,095 | 0.73% | 2,126 | 42 | City |
| Greenwich | 4 | 65,196 | 63,328 | 0.93% | 1,366 | 48 | Township |
| New Milford | 5 | 28,999 | 27,982 | 0.88% | 471 | 62 | Township |
| Westport | 6 | 28,309 | 27,069 | 1.12% | 1,418 | 20 | Township |
| Newtown | 7 | 28,209 | 27,037 | 0.64% | 490 | 58 | Township |
| Ridgefield | 8 | 25,470 | 24,955 | 0.67% | 738 | 35 | Township |
| Darien | 9 | 22,866 | 21,445 | 1.5% | 1,807 | 13 | Township |
| Bethel | 10 | 22,137 | 20,324 | 3.01% | 1,305 | 17 | Township |
| New Canaan | 11 | 21,297 | 20,535 | 0.65% | 960 | 22 | Township |
| Wilton | 12 | 19,378 | 18,403 | 0.64% | 723 | 27 | Township |
| Brookfield | 13 | 18,554 | 17,469 | 2.02% | 940 | 20 | Township |
| Greenwich | 14 | 14,328 | 12,967 | 0.65% | 2,959 | 5 | CDP |
| New Fairfield | 15 | 13,710 | 13,531 | 0.43% | 671 | 20 | Township |
| Bethel | 16 | 12,052 | 10,839 | 1.41% | 1,956 | 6 | CDP |
| Weston | 17 | 10,553 | 10,320 | 0.6% | 534 | 20 | Township |
| Redding | 18 | 8,873 | 8,732 | 0.49% | 282 | 31 | Township |
| New Canaan | 19 | 8,579 | 7,256 | 7.14% | 5,538 | 2 | CDP |
| Ridgefield | 20 | 7,657 | 7,228 | 0% | 1,224 | 6 | CDP |
| New Milford | 21 | 7,238 | 6,749 | 0.67% | 1,780 | 4 | CDP |
| Sherman | 22 | 3,641 | 3,515 | 1.11% | 166 | 22 | Township |
| Newtown | 23 | 1,998 | 1,907 | 0.91% | 867 | 2 | Borough |
| Bridgewater | 24 | 1,682 | 1,651 | 0.66% | 103 | 16 | Township |
| Weston | 25 | 996 | 632 | 7.1% | 664 | 1 | CDP |
| Bridgewater | 26 | 178 | 159 | 7.23% | 654 | 0 | CDP |
| Sherman | 27 | 41 | 60 | 7.89% | 117 | 0 | CDP |
Stamford is the largest city in Western CT Planning Region, with a population of 140,049.
Sherman is the smallest city in Western CT Planning Region, with a population of 41.
There are 27 cities in Western CT Planning Region, Connecticut.