Southwest Connecticut Cities

City	Rank	County	2026 Pop. ↓
Bridgeport	1	Greater Bridgeport Planning Region	153,542
Stamford	2	Western Connecticut Planning Region	140,964
Waterbury	3	Naugatuck Valley Planning Region	116,917
Norwalk	4	Western Connecticut Planning Region	95,043
Danbury	5	Western Connecticut Planning Region	89,990
Fairfield	6	Greater Bridgeport Planning Region	67,470
Greenwich	7	Western Connecticut Planning Region	65,798
Bristol	8	Naugatuck Valley Planning Region	62,920
Stratford	9	Greater Bridgeport Planning Region	54,934
Shelton	10	Naugatuck Valley Planning Region	43,826
Trumbull	11	Greater Bridgeport Planning Region	39,015
Cheshire	12	Naugatuck Valley Planning Region	33,380
Naugatuck	13	Naugatuck Valley Planning Region	32,427
New Milford	14	Western Connecticut Planning Region	29,253
Westport	15	Western Connecticut Planning Region	28,622
Newtown	16	Western Connecticut Planning Region	28,389
Ridgefield	17	Western Connecticut Planning Region	25,640
Darien	18	Western Connecticut Planning Region	23,204
Watertown	19	Naugatuck Valley Planning Region	22,787
Bethel	20	Western Connecticut Planning Region	22,784
New Canaan	21	Western Connecticut Planning Region	21,434
Southbury	22	Naugatuck Valley Planning Region	20,624
Monroe	23	Greater Bridgeport Planning Region	19,765
Wilton	24	Western Connecticut Planning Region	19,501
Ansonia	25	Naugatuck Valley Planning Region	19,344
Brookfield	26	Western Connecticut Planning Region	18,922
Seymour	27	Naugatuck Valley Planning Region	17,389
Wolcott	28	Naugatuck Valley Planning Region	16,739
New Fairfield	29	Western Connecticut Planning Region	13,769
Oxford	30	Naugatuck Valley Planning Region	13,444
Derby	31	Naugatuck Valley Planning Region	13,216
Plymouth	32	Naugatuck Valley Planning Region	12,011
Weston	33	Western Connecticut Planning Region	10,616
Woodbury	34	Naugatuck Valley Planning Region	10,094
Prospect	35	Naugatuck Valley Planning Region	9,685
Redding	36	Western Connecticut Planning Region	8,916
Middlebury	37	Naugatuck Valley Planning Region	8,157
Easton	38	Greater Bridgeport Planning Region	8,037
Thomaston	39	Naugatuck Valley Planning Region	7,634
Beacon Falls	40	Naugatuck Valley Planning Region	6,375
Sherman	41	Western Connecticut Planning Region	3,681
Bethlehem	42	Naugatuck Valley Planning Region	3,477
Bridgewater	43	Western Connecticut Planning Region	1,693

City

Rank

County

2026 Pop. ↓

Bridgeport

Greater Bridgeport Planning Region

153,542

Stamford

Western Connecticut Planning Region

140,964

Waterbury

Naugatuck Valley Planning Region