Southwest Connecticut Cities

City	Rank	County	2026 Pop. ↓
Bridgeport	1	Greater Bridgeport Planning Region	153,208
Stamford	2	Western Connecticut Planning Region	140,509
Waterbury	3	Naugatuck Valley Planning Region	116,177
Norwalk	4	Western Connecticut Planning Region	95,205
Danbury	5	Western Connecticut Planning Region	89,744
Fairfield	6	Greater Bridgeport Planning Region	66,622
Greenwich	7	Western Connecticut Planning Region	64,960
Bristol	8	Naugatuck Valley Planning Region	62,686
Stratford	9	Greater Bridgeport Planning Region	54,071
Shelton	10	Naugatuck Valley Planning Region	43,388
Trumbull	11	Greater Bridgeport Planning Region	37,999
Naugatuck	12	Naugatuck Valley Planning Region	32,380
Cheshire	13	Naugatuck Valley Planning Region	31,393
New Milford	14	Western Connecticut Planning Region	29,098
Westport	15	Western Connecticut Planning Region	28,629
Newtown	16	Western Connecticut Planning Region	28,288
Ridgefield	17	Western Connecticut Planning Region	25,448
Darien	18	Western Connecticut Planning Region	22,627
Watertown	19	Naugatuck Valley Planning Region	22,574
Bethel	20	Western Connecticut Planning Region	21,847
New Canaan	21	Western Connecticut Planning Region	21,262
Southbury	22	Naugatuck Valley Planning Region	20,597
Wilton	23	Western Connecticut Planning Region	19,570
Monroe	24	Greater Bridgeport Planning Region	19,343
Ansonia	25	Naugatuck Valley Planning Region	19,282
Brookfield	26	Western Connecticut Planning Region	18,945
Seymour	27	Naugatuck Valley Planning Region	17,196
Wolcott	28	Naugatuck Valley Planning Region	16,661
New Fairfield	29	Western Connecticut Planning Region	13,683
Oxford	30	Naugatuck Valley Planning Region	13,374
Derby	31	Naugatuck Valley Planning Region	13,071
Plymouth	32	Naugatuck Valley Planning Region	11,941
Weston	33	Western Connecticut Planning Region	10,536
Woodbury	34	Naugatuck Valley Planning Region	10,056
Prospect	35	Naugatuck Valley Planning Region	9,675
Redding	36	Western Connecticut Planning Region	8,859
Middlebury	37	Naugatuck Valley Planning Region	8,165
Easton	38	Greater Bridgeport Planning Region	7,837
Thomaston	39	Naugatuck Valley Planning Region	7,591
Beacon Falls	40	Naugatuck Valley Planning Region	6,341
Sherman	41	Western Connecticut Planning Region	3,643
Bethlehem	42	Naugatuck Valley Planning Region	3,468
Bridgewater	43	Western Connecticut Planning Region	1,680

City

Rank

County

2026 Pop. ↓

Bridgeport

Greater Bridgeport Planning Region

153,208

Stamford

Western Connecticut Planning Region

140,509

Waterbury

Naugatuck Valley Planning Region