24 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Randolph town | 1 | 4,835 | 4,772 | -0.14% | 101 | 47.97 | Town |
| Williamstown town | 2 | 3,623 | 3,521 | 0.3% | 90 | 40.16 | Town |
| Thetford town | 3 | 2,856 | 2,775 | 0.28% | 66 | 43.55 | Town |
| Bradford town | 4 | 2,841 | 2,790 | 0.11% | 96 | 29.66 | Town |
| Newbury town | 5 | 2,378 | 2,292 | 0.13% | 37 | 64.05 | Town |
| Randolph | 6 | 2,019 | 2,044 | 0.15% | 451 | 4.47 | CDP |
| Williamstown | 7 | 1,594 | 1,253 | 1.79% | 475 | 3.36 | CDP |
| Corinth town | 8 | 1,508 | 1,458 | 0.47% | 31 | 48.24 | Town |
| Bradford | 9 | 1,393 | 925 | 2.96% | 1,465 | 0.95 | CDP |
| Tunbridge town | 10 | 1,381 | 1,343 | 0.29% | 31 | 44.64 | Town |
| Brookfield town | 11 | 1,288 | 1,249 | 0.31% | 32 | 40.88 | Town |
| Chelsea town | 12 | 1,271 | 1,232 | 0.39% | 32 | 40.05 | Town |
| Topsham town | 13 | 1,234 | 1,199 | 0.33% | 25 | 48.92 | Town |
| Braintree town | 14 | 1,218 | 1,205 | -0.08% | 32 | 38.45 | Town |
| Strafford town | 15 | 1,099 | 1,095 | -0.27% | 25 | 44.09 | Town |
| Orange town | 16 | 1,094 | 1,057 | 0.55% | 28 | 38.69 | Town |
| Fairlee town | 17 | 1,060 | 987 | 1.53% | 53 | 19.97 | Town |
| Washington town | 18 | 1,056 | 1,030 | -0.09% | 27 | 38.98 | Town |
| Vershire town | 19 | 692 | 673 | 0.29% | 19 | 36.10 | Town |
| West Fairlee town | 20 | 635 | 617 | 0.32% | 28 | 22.62 | Town |
| Chelsea | 21 | 608 | 463 | 7.23% | 685 | 0.89 | CDP |
| Newbury | 22 | 468 | 442 | 1.08% | 94 | 4.96 | Village |
| Wells River | 23 | 461 | 436 | 1.1% | 244 | 1.89 | Village |
| Fairlee | 24 | 102 | 163 | -4.67% | 169 | 0.60 | CDP |
Randolph town is the largest city in Orange County, with a population of 4,835.
Fairlee is the smallest city in Orange County.
There are 24 cities in Orange County, Vermont.