| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Stamford | 1 | 140,509 | 135,447 | 0.7% | 3,734 | 38 | City |
| Norwalk | 2 | 95,205 | 90,926 | 0.74% | 4,160 | 23 | City |
| Danbury | 3 | 89,744 | 86,078 | 0.8% | 2,135 | 42 | City |
| Greenwich | 4 | 64,960 | 63,336 | 0.25% | 1,361 | 48 | Township |
| New Milford | 5 | 29,098 | 27,983 | 0.54% | 473 | 62 | Township |
| Westport | 6 | 28,629 | 27,040 | 1.16% | 1,434 | 20 | Township |
| Newtown | 7 | 28,288 | 27,050 | 0.37% | 492 | 58 | Township |
| Ridgefield | 8 | 25,448 | 24,945 | 0.3% | 738 | 35 | Township |
| Darien | 9 | 22,627 | 21,457 | 0.19% | 1,788 | 13 | Township |
| Bethel | 10 | 21,847 | 20,338 | 0.76% | 1,288 | 17 | Township |
| New Canaan | 11 | 21,262 | 20,515 | 0.25% | 958 | 22 | Township |
| Wilton | 12 | 19,570 | 18,430 | 0.69% | 731 | 27 | Township |
| Brookfield | 13 | 18,945 | 17,460 | 2.04% | 960 | 20 | Township |
| New Fairfield | 14 | 13,683 | 13,538 | 0.07% | 670 | 20 | Township |
| Weston | 15 | 10,536 | 10,320 | 0.18% | 533 | 20 | Township |
| Redding | 16 | 8,859 | 8,720 | 0.14% | 281 | 31 | Township |
| Sherman | 17 | 3,643 | 3,505 | 0.69% | 166 | 22 | Township |
| Bridgewater | 18 | 1,680 | 1,652 | 0.18% | 102 | 16 | Township |
Stamford is the largest city in Western Connecticut Planning Region, with a population of 140,509.
Bridgewater is the smallest city in Western Connecticut Planning Region, with a population of 1,680.
There are 18 cities in Western Connecticut Planning Region, Connecticut.