56 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Middlebury | 1 | 9,234 | 9,147 | 0.22% | 235 | 39 | Town |
| Middlebury | 2 | 9,234 | 9,149 | 0.22% | 235 | 39 | Town |
| Middlebury | 3 | 6,994 | 6,929 | 0.39% | 493 | 14 | CDP |
| Bristol | 4 | 3,777 | 3,779 | -0.05% | 93 | 41 | Town |
| Bristol | 5 | 3,777 | 3,775 | -0.05% | 93 | 41 | Town |
| Ferrisburgh | 6 | 2,705 | 2,644 | 0.56% | 57 | 47 | Town |
| Ferrisburgh | 7 | 2,705 | 2,642 | 0.56% | 57 | 47 | Town |
| Vergennes | 8 | 2,589 | 2,554 | 0.27% | 1,054 | 2 | City |
| Vergennes | 9 | 2,589 | 2,554 | 0.27% | 1,054 | 2 | City |
| Monkton | 10 | 2,222 | 2,075 | 1.18% | 62 | 36 | Town |
| Monkton | 11 | 2,222 | 2,076 | 1.18% | 62 | 36 | Town |
| Bristol | 12 | 1,937 | 2,095 | -0.36% | 812 | 2 | CDP |
| Starksboro | 13 | 1,823 | 1,756 | 0.61% | 40 | 45 | Town |
| Starksboro | 14 | 1,823 | 1,757 | 0.61% | 40 | 45 | Town |
| New Haven | 15 | 1,749 | 1,699 | 0.29% | 42 | 41 | Town |
| New Haven | 16 | 1,749 | 1,701 | 0.29% | 42 | 41 | Town |
| Lincoln | 17 | 1,395 | 1,328 | 1.16% | 31 | 46 | Town |
| Lincoln | 18 | 1,395 | 1,328 | 1.16% | 31 | 46 | Town |
| Addison | 19 | 1,348 | 1,355 | -0.22% | 32 | 42 | Town |
| Addison | 20 | 1,348 | 1,353 | -0.22% | 32 | 42 | Town |
| Cornwall | 21 | 1,315 | 1,209 | 1.62% | 46 | 29 | Town |
| Cornwall | 22 | 1,315 | 1,209 | 1.62% | 46 | 29 | Town |
| Shoreham | 23 | 1,298 | 1,251 | 0.85% | 30 | 43 | Town |
| Shoreham | 24 | 1,298 | 1,249 | 0.85% | 30 | 43 | Town |
| Salisbury | 25 | 1,259 | 1,222 | 1.04% | 44 | 29 | Town |
| Salisbury | 26 | 1,259 | 1,220 | 1.04% | 44 | 29 | Town |
| Orwell | 27 | 1,256 | 1,249 | 0.08% | 27 | 47 | Town |
| Orwell | 28 | 1,256 | 1,247 | 0.08% | 27 | 47 | Town |
| Bridport | 29 | 1,252 | 1,227 | 0.4% | 29 | 44 | Town |
| Bridport | 30 | 1,252 | 1,227 | 0.4% | 29 | 44 | Town |
| Leicester | 31 | 1,025 | 989 | 0.69% | 49 | 21 | Town |
| Leicester | 32 | 1,025 | 990 | 0.69% | 49 | 21 | Town |
| Weybridge | 33 | 845 | 811 | 0.96% | 49 | 17 | Town |
| Weybridge | 34 | 845 | 812 | 0.96% | 49 | 17 | Town |
| Ripton | 35 | 742 | 735 | -0.27% | 15 | 49 | Town |
| Ripton | 36 | 742 | 735 | -0.27% | 15 | 49 | Town |
| Panton | 37 | 666 | 649 | 0% | 43 | 15 | Town |
| Panton | 38 | 666 | 652 | 0% | 43 | 15 | Town |
| Roxbury | 39 | 666 | 679 | -1.19% | 16 | 42 | Town |
| Roxbury | 40 | 666 | 678 | -1.19% | 16 | 42 | Town |
| East Middlebury | 41 | 497 | 381 | 0.81% | 680 | 1 | CDP |
| Waltham | 42 | 453 | 447 | 0.44% | 50 | 9 | Town |
| Waltham | 43 | 453 | 446 | 0.44% | 50 | 9 | Town |
| Whiting | 44 | 407 | 404 | -0.25% | 30 | 14 | Town |
| Whiting | 45 | 407 | 403 | -0.25% | 30 | 14 | Town |
| Hancock | 46 | 359 | 355 | 0.28% | 9 | 38 | Town |
| Hancock | 47 | 359 | 354 | 0.28% | 9 | 38 | Town |
| Lincoln | 48 | 324 | 225 | 7.28% | 137 | 2 | CDP |
| Granville | 49 | 303 | 301 | -0.33% | 6 | 51 | Town |
| Granville | 50 | 303 | 301 | -0.33% | 6 | 51 | Town |
| New Haven | 51 | 210 | 139 | 7.14% | 79 | 3 | CDP |
| South Lincoln | 52 | 191 | 150 | 7.3% | 80 | 2 | CDP |
| Goshen | 53 | 188 | 174 | 1.62% | 9 | 21 | Town |
| Goshen | 54 | 188 | 174 | 1.62% | 9 | 21 | Town |
| Huntington Center | 55 | 148 | 150 | 7.25% | 493 | 0 | CDP |
| Hanksville | 56 | 41 | 23 | 7.89% | 313 | 0 | CDP |
Middlebury is the largest city in Addison County, with a population of 9,234.
Hanksville is the smallest city in Addison County, with a population of 41.
There are 56 cities in Addison County, Vermont.