| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Torrington | 1 | 35,888 | 35,361 | 0.26% | 903 | 40 | City |
| Winchester | 2 | 10,374 | 10,259 | 0.14% | 319 | 33 | Township |
| Burlington | 3 | 9,926 | 9,484 | 0.53% | 334 | 30 | Township |
| Litchfield | 4 | 8,412 | 8,185 | 0.37% | 150 | 56 | Township |
| New Hartford | 5 | 6,775 | 6,612 | 0.4% | 183 | 37 | Township |
| Harwinton | 6 | 5,807 | 5,474 | 0.97% | 189 | 31 | Township |
| Salisbury | 7 | 4,300 | 4,190 | 0.23% | 75 | 57 | Township |
| Barkhamsted | 8 | 3,750 | 3,625 | 0.64% | 103 | 36 | Township |
| Washington | 9 | 3,743 | 3,636 | 0.27% | 98 | 38 | Township |
| Goshen | 10 | 3,324 | 3,150 | 0.79% | 76 | 44 | Township |
| North Canaan | 11 | 3,240 | 3,199 | 0.28% | 167 | 19 | Township |
| Kent | 12 | 3,118 | 3,016 | 0.55% | 64 | 49 | Township |
| Sharon | 13 | 2,804 | 2,681 | 0.75% | 48 | 59 | Township |
| Roxbury | 14 | 2,344 | 2,252 | 0.69% | 89 | 26 | Township |
| Morris | 15 | 2,311 | 2,243 | 0.48% | 133 | 17 | Township |
| Hartland | 16 | 1,932 | 1,898 | 0.21% | 59 | 33 | Township |
| Norfolk | 17 | 1,606 | 1,583 | 0.06% | 35 | 45 | Township |
| Cornwall | 18 | 1,590 | 1,567 | 0.06% | 35 | 46 | Township |
| Warren | 19 | 1,398 | 1,350 | 0.65% | 53 | 26 | Township |
| Colebrook | 20 | 1,391 | 1,365 | 0.22% | 44 | 32 | Township |
| Canaan | 21 | 1,093 | 1,076 | 0.18% | 33 | 33 | Township |
Torrington is the largest city in Northwest Hills Planning Region, with a population of 35,888.
Canaan is the smallest city in Northwest Hills Planning Region, with a population of 1,093.
There are 21 cities in Northwest Hills Planning Region, Connecticut.