Known as one of the most scenic and magnificent states in the country, Connecticut is small but mighty. Those who live in the state prefer to stay there, and those who visit don’t want to leave!

Memorial Chapel by Night

Its location at the southern tip of New England may only hold a little over 5,000 square miles, but what land there is is packed with diversity and history. Connecticut is well-known for its impressive college campuses, breathtaking landscapes, and long history.

As traditional as the state may be, there are plenty of big cities to choose from that offer the conveniences of modern living. Some are known for their proximity to colleges, while others are better for finding jobs in innovative industries like finance or cannabis retail now that the Constitution State has legalized weed. (Note that if you don’t want to pay exorbitant excise taxes for your cannabis and you want access to high-quality products, invest in an MMJ license from reputable companies like Veriheal.)

Here, we’ll discuss the three largest cities in Connecticut and their pros and cons to help you decide where your next home will be!

1. Bridgeport

Connecticut’s population hovers at around 3.6 million people, making it the second-most populous state in New England. Of those millions, nearly 150,000 residents choose Bridgeport as their home city.

This city is made up of over 70 different neighborhoods. Bridgeport is home to 70 different neighborhoods, all close to nearby LaGuardia Airport and Bradley International Airport.

Because it’s only a little over an hour from Manhattan, many people who work in the Big Apple live in Bridgeport to save on expenses. Although the cost of living here is slightly higher than the national average, it’s typically cheaper than living in NYC. Bridgeport is one of the wealthiest cities in America.

The city is known for its beautiful sandy beaches, vast forests, and expanses of open nature.

One more interesting tidbit about this city is that it is nicknamed “Park City” due to its many public parks. Seaside Park and Beardsley Park are two of the most popular, and both were designed and built by Frederick Law Olmsted, the same designer of Central Park in NYC.

2. New Haven

With a population of just over 131,000 residents, New Haven is a bustling city that also retains the traditional air of its rich cultural history — including its location as home of one of the most prestigious universities in the world, Yale.

In addition to its top-tier education, New Haven is also known for its impressive music and arts scene and culinary opportunities.

Although it’s a large city, much of the heart of New Haven is walkable, with vast stretches of sidewalks, forest paths, and trails. Neighborhoods are close to each other, and it’s easy to find convenient shopping and restaurants wherever you live.

On the downside, having a prestigious university and some of the top restaurants in the country means you’ll have to pay for those privileges. New Haven’s cost of living and housing is higher than the national average, with homes ranging anywhere up to 35% more than in other cities.

3. Stamford

Stamford has a reputation as home to some of the most educated people in the country, which is likely related to its high safety rating (using the statistic of having lower than average property and violent crime).

In keeping with its reputation, Stamford houses multiple top-tier schools and an up-to-date arts and entertainment area downtown. In fact, some say that this city is the best place to live in the state.

What makes it so impressive? Stamford has a coveted balance of urban and suburban living, including parks, shops, restaurants, and museums. It’s also popular with young professionals and families due to the jobs and top schools in the area. However, the cost of living is higher than the national average.

While not as walkable as New Haven, Stamford does give you plenty of places to explore the great outdoors. If you’re looking for a solid place to raise your children (or start a family) or an excellent city geared toward professionals, consider Stamford.


No matter where you move to in Connecticut, you’re going to have some consistent benefits: gorgeous scenery, rich history, diverse culture, and a vibrant mix of seasons. From there, the final decision comes down to which of these three major cities holds your preferred lifestyle.

, 3 of the Largest Cities in Connecticut to Consider Moving to, Days of a Domestic Dad