19 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Stamford | 1 | 140,964 | 135,474 | 0.65% | 3,746 | 38 | City |
| Norwalk | 2 | 95,043 | 90,897 | 0.73% | 4,153 | 23 | City |
| Danbury | 3 | 89,990 | 86,095 | 0.73% | 2,141 | 42 | City |
| Greenwich | 4 | 65,798 | 63,328 | 0.92% | 1,379 | 48 | Township |
| New Milford | 5 | 29,253 | 27,982 | 0.88% | 475 | 62 | Township |
| Westport | 6 | 28,622 | 27,069 | 1.11% | 1,434 | 20 | Township |
| Newtown | 7 | 28,389 | 27,037 | 0.64% | 493 | 58 | Township |
| Ridgefield | 8 | 25,640 | 24,955 | 0.67% | 743 | 35 | Township |
| Darien | 9 | 23,204 | 21,445 | 1.48% | 1,834 | 13 | Township |
| Bethel | 10 | 22,784 | 20,324 | 2.92% | 1,344 | 17 | Township |
| New Canaan | 11 | 21,434 | 20,535 | 0.64% | 966 | 22 | Township |
| Wilton | 12 | 19,501 | 18,403 | 0.63% | 728 | 27 | Township |
| Brookfield | 13 | 18,922 | 17,469 | 1.98% | 959 | 20 | Township |
| New Fairfield | 14 | 13,769 | 13,531 | 0.43% | 674 | 20 | Township |
| Weston | 15 | 10,616 | 10,320 | 0.6% | 537 | 20 | Township |
| Redding | 16 | 8,916 | 8,732 | 0.48% | 283 | 31 | Township |
| Sherman | 17 | 3,681 | 3,515 | 1.1% | 168 | 22 | Township |
| Newtown | 18 | 2,016 | 1,907 | 0.9% | 875 | 2 | Borough |
| Bridgewater | 19 | 1,693 | 1,651 | 0.65% | 103 | 16 | Township |
Stamford is the largest city in Western CT Planning Region, with a population of 140,964.
Bridgewater is the smallest city in Western CT Planning Region, with a population of 1,693.
There are 19 cities in Western CT Planning Region, Connecticut.