01 · the cities
Bridgeport
Bridgeport is the largest city in Connecticut, sitting on Long Island Sound with a working harbor and a real waterfront. P.T. Barnum lived here and the city's museum still pays tribute to his weird genius. It's a quick train ride to New York, with much cheaper housing and proper New England summers. The food scene punches above its weight, with old-school Portuguese and Brazilian spots packed every weekend.
full dispatch→Winston-Salem
Winston-Salem is Moravian cookie traditions, old tobacco wealth (R.J. Reynolds), and Krispy Kreme's hometown (the original hot doughnut sign is still here). Old Salem is a living history Moravian village downtown. The food scene has picked up nicely, the arts scene leans on the University of North Carolina School of the Arts. Slower-paced than its Triad neighbors. A little secret.
full dispatch→02 · the money
Median rent
Median rent
$2,767/mo
$1,508/mo
$1,259/mo less than Bridgeport (83%)
Median home price
Median home price
$768k
$283k
$485k less than Bridgeport
State income tax
State income tax
5.5%
4.5%
Gross left after rent
Gross left after rent
$5,108/mo
$6,450/mo
Winston-Salem has $1,342/mo more gross after rent at $100k
Gross left after rent reflects state income tax but not federal, based on $100k salary. Enter your salary to find your ideal city.
03 · the weather
Pleasant days/yr
Pleasant days/yr
172 days
186 days
14 more than Bridgeport
Extreme heat days
Extreme heat days
0 days
8 days
days above 95°F per year
Extreme cold days
Extreme cold days
15 days
6 days
days below 20°F per year
Winston-Salem has 8 more days above 95°F each year than Bridgeport. Bridgeport drops below 20°F on 9 more days per year than Winston-Salem.
04 · the life
OutdoorScore
OutdoorScore
64 / 100
54 / 100
10.0 pts behind Bridgeport
Nonstop flights
Nonstop flights
1 routes
0 routes
Metro size
Metro size
952k metro
696k metro
the verdict
2
Bridgeport
categories won
6
Winston-Salem
categories won
Winston-Salem wins on money and weather. Bridgeport has the edge on lifestyle.
run your numbers
How far does your Bridgeport salary go?
Enter your salary to see a full ranked list of cities where you would live better.
see your top citiesWe use a proprietary blend of data from the US Census, Zillow, Ticketmaster, and more.
Walk Score® is a trademark of Walk Score, a Redfin company. How Walk Score works

