Southwest Connecticut Cities

43 cities

City
Rank
County
2026 Pop.
Bridgeport1Greater Bridgeport Planning Region153,542
Stamford2Western CT Planning Region140,964
Waterbury3Naugatuck Valley Planning Region116,917
Norwalk4Western CT Planning Region95,043
Danbury5Western CT Planning Region89,990
Fairfield6Greater Bridgeport Planning Region67,470
Greenwich7Western CT Planning Region65,798
Bristol8Naugatuck Valley Planning Region62,920
Stratford9Greater Bridgeport Planning Region54,934
Shelton10Naugatuck Valley Planning Region43,826
Trumbull11Greater Bridgeport Planning Region39,015
Cheshire12Naugatuck Valley Planning Region33,380
Naugatuck13Naugatuck Valley Planning Region32,427
New Milford14Western CT Planning Region29,253
Westport15Western CT Planning Region28,622
Newtown16Western CT Planning Region28,389
Ridgefield17Western CT Planning Region25,640
Darien18Western CT Planning Region23,204
Watertown19Naugatuck Valley Planning Region22,787
Bethel20Western CT Planning Region22,784
New Canaan21Western CT Planning Region21,434
Southbury22Naugatuck Valley Planning Region20,624
Monroe23Greater Bridgeport Planning Region19,765
Wilton24Western CT Planning Region19,501
Ansonia25Naugatuck Valley Planning Region19,344
Brookfield26Western CT Planning Region18,922
Seymour27Naugatuck Valley Planning Region17,389
Wolcott28Naugatuck Valley Planning Region16,739
New Fairfield29Western CT Planning Region13,769
Oxford30Naugatuck Valley Planning Region13,444
Derby31Naugatuck Valley Planning Region13,216
Plymouth32Naugatuck Valley Planning Region12,011
Weston33Western CT Planning Region10,616
Woodbury34Naugatuck Valley Planning Region10,094
Prospect35Naugatuck Valley Planning Region9,685
Redding36Western CT Planning Region8,916
Middlebury37Naugatuck Valley Planning Region8,157
Easton38Greater Bridgeport Planning Region8,037
Thomaston39Naugatuck Valley Planning Region7,634
Beacon Falls40Naugatuck Valley Planning Region6,375
Sherman41Western CT Planning Region3,681
Bethlehem42Naugatuck Valley Planning Region3,477
Bridgewater43Western CT Planning Region1,693

About Southwest Connecticut

Western CT Planning Region, Naugatuck Valley Planning Region, and Greater Bridgeport Planning Region are the counties generally considered part of Southwest Connecticut.