| Rank | City | 2000 Population |
|---|---|---|
| 1 | Groton Long Point | 669 |
| 2 | Waterbury | 107,311 |
| 3 | Groton | 9,292 |
| 4 | Norwalk | 83,061 |
| 5 | New Britain | 71,558 |
| 6 | Bristol | 60,288 |
| 7 | Milford | 50,695 |
| 8 | Middletown | 45,681 |
| 9 | Bantam | 802 |
| 10 | Norwich | 36,131 |
| 11 | Fenwick | 52 |
| 12 | Derby | 12,400 |
| 13 | Danielson | 4,261 |
| 14 | Jewett City | 3,053 |
| 15 | Newtown | 1,844 |
| 16 | Naugatuck | 31,027 |
| 17 | New London | 26,183 |
| 18 | Ansonia | 18,570 |
| 19 | Woodmont | 1,713 |
| 20 | Litchfield | 1,328 |
| 21 | Stonington | 1,032 |
| 22 | Bridgeport | 139,650 |
| 23 | Hartford | 124,178 |
| 24 | New Haven | 123,759 |
| 25 | Stamford | 117,483 |
| 26 | Danbury | 75,112 |
| 27 | Meriden | 58,271 |
| 28 | West Haven | 52,372 |
| 29 | Shelton | 38,201 |
| 30 | Torrington | 35,239 |
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