22 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Torrington | 1 | 35,750 | 35,363 | 0.22% | 899 | 40 | City |
| Winchester | 2 | 10,337 | 10,242 | 0.27% | 318 | 33 | Township |
| Burlington | 3 | 9,865 | 9,487 | 0.62% | 332 | 30 | Township |
| Litchfield | 4 | 8,365 | 8,182 | 0.38% | 149 | 56 | Township |
| New Hartford | 5 | 6,739 | 6,614 | 0.43% | 182 | 37 | Township |
| Harwinton | 6 | 5,760 | 5,474 | 1.27% | 187 | 31 | Township |
| Salisbury | 7 | 4,310 | 4,189 | 0.72% | 75 | 57 | Township |
| Barkhamsted | 8 | 3,754 | 3,645 | 1% | 104 | 36 | Township |
| Washington | 9 | 3,748 | 3,639 | 0.73% | 98 | 38 | Township |
| Goshen | 10 | 3,295 | 3,150 | 0.92% | 76 | 44 | Township |
| North Canaan | 11 | 3,229 | 3,197 | 0.28% | 167 | 19 | Township |
| Kent | 12 | 3,100 | 3,017 | 0.52% | 64 | 49 | Township |
| Sharon | 13 | 2,766 | 2,678 | 0.4% | 47 | 59 | Township |
| Roxbury | 14 | 2,323 | 2,253 | 0.56% | 88 | 26 | Township |
| Morris | 15 | 2,308 | 2,247 | 0.79% | 133 | 17 | Township |
| Hartland | 16 | 1,930 | 1,896 | 0.47% | 58 | 33 | Township |
| Norfolk | 17 | 1,607 | 1,582 | 0.37% | 35 | 45 | Township |
| Cornwall | 18 | 1,593 | 1,566 | 0.5% | 35 | 46 | Township |
| Warren | 19 | 1,388 | 1,349 | 0.73% | 53 | 26 | Township |
| Colebrook | 20 | 1,374 | 1,353 | 0.29% | 44 | 32 | Township |
| Litchfield | 21 | 1,216 | 1,189 | 0.41% | 886 | 1 | Borough |
| Canaan | 22 | 1,093 | 1,076 | 0.46% | 33 | 33 | Township |
Torrington is the largest city in Northwest Hills Planning Region, with a population of 35,750.
Canaan is the smallest city in Northwest Hills Planning Region, with a population of 1,093.
There are 22 cities in Northwest Hills Planning Region, Connecticut.