Boston’s history and geography have shaped the city into something unique. It has its own specific way of doing and saying things, a local culture that many find charming, and a climate that really separates the snowbirds from the sunbirds. But just like 50 inches of snow can be a nightmare to some and a joy to others, the charm of some of Boston’s other traits depends on whom you’re talking to.

In order to find out what are the ups and downs of living in Boston, we asked Bostonians themselves. Their answers afforded us a glimpse into what life is like in “Beantown”, but also what people pay most attention to when thinking about the city they live in.

Pro: Boston Is Walkable

Boston was founded almost 400 years ago, which means the city’s layout doesn’t revolve around a grid system and is not as vehicle-centric as other U.S. cities, especially those on the West Coast. This means it is very pedestrian-friendly and you can reach a lot of places by foot.

historic street in boston with brick buildings and cobblestone

“It is a great place to live and work, many neighborhoods are walkable/close to food (casual, fancy, ethnic, grocery), music, bars, movies, subway stops, drug stores, post office, parks, bike trails, local shops, etc.,” said Paige Arnof-Fenn, founder and CEO of marketing firm Mavens & Moguls, based in Cambridge, right across the river from Boston.

Con: Boston Traffic Is Bad

Saying traffic is bad is like saying water is wet, but it seems to be a particularly annoying issue for Bostonians. Many praise the local infrastructure but blame the drivers themselves. Most traffic accidents occur around Morton Street and Gallivan Boulevard, and half of all accidents occur on weekends. Storrow Drive is notorious for trucks getting stuck underneath it, giving rise to the expression “getting Storrowed.” If you’re out driving in Boston, remember to keep your cool!

“There is a well-deserved reputation among Bostonians and eastern Massachusettsians in general for being terrible drivers,” confirmed Max Shak, founder at “In spite of the fact that we don’t necessarily lack skills, we are pretty impatient, which shows. Unless you’re careful, you will become one.”

Pro: Boston Schools Are Great

You’ve heard of MIT and Berklee, but Boston is filled to the brim with not only prestigious colleges but many high-performing public schools. The city is also home to the Boston Latin School, the oldest existing school in the U.S., so its educational history goes way back. In fact, Boston is one of the most educated cities in the country, with over half of its population over 25 years of age holding a bachelor’s degree.

Thomas Villalpando, online entrepreneur and co-founder of, said “There are many public schools and universities in Boston with high-quality education. There are more than 125 public schools. For example, Boston Latin School is ranked 36th in the entire country.”

students holding diplomas

Con: High Cost of Living

It’s no secret that Boston isn’t cheap. In fact, it’s quite the opposite, as Boston is slightly more expensive to live in than some West Coast cities like Los Angeles or San Diego, but it is still significantly cheaper than places like New York City or Washington, D.C. “The cost of living in Boston is very high, and many people need two jobs to make ends meet,” Shak told us.

The housing market is expensive as well, whether you’re looking to buy or rent in Boston. It’s a very densely packed city, and the average apartment size is just 812 square feet. This means residents must make the most of their available space by turning to alternative solutions like self storage. A 10’x10’ non climate-controlled storage unit in Boston goes for $193 per month on average, but there are places like Extra Space Storage in Roxbury where you can find such units for as cheap as $151 per month.

Pro: Boston Public Transport

To avoid traffic as much as possible, residents make good use of Boston’s public transportation system. In 2020, while the pandemic was in full swing, Boston still had almost 150 million people take public transportation, which shows just how much people either love the T or hate the turnpike. John Dave, founder and director at has lived in Boston since 2020 and thinks that “the infrastructure is top-notch, with reliable public transportation and a clean, well-maintained city.”

Con: Boston Public Transport

You might be a bit confused to see the same point again, but the truth is that the public transportation system in Boston seems to be a matter of intense debate among residents. You can either love it or hate it, and people do both! Just ask Shak: “As for the train, it’s awful. I just don’t understand. Other than the Blue Line, each of the other lines either breaks, fills with smoke, freezes or gets delayed by at least 20 minutes. For now, we must live with high blood pressure while they fix this problem — building new trains.”

boston green line metro

Pro: Great Job Market

With great education comes a great job market, and Boston certainly doesn’t disappoint! Some of the biggest companies and corporations in the world have a presence in the city, benefitting from all the young, highly educated graduates who are eager to put their knowledge to use.

Villalpando confirmed that “Boston has a very strong job market. There are lots of high-paying job opportunities available. Some big offices include Amazon, Microsoft, Google, Pfizer, and Fidelity Investments, also available in Boston. A lot of people decided to move to Boston because there is a big job market in different industries like technology, construction, financial, and health.”

The mean hourly wage for the Boston metropolitan area is 32% higher than the national average, and rightfully so, given what we know about the cost of living.

Con: Winters Are Bitter

Boston winters are no laughing matter! Ben Hartwig, web operations executive at InfoTracer confirms that “winters in Boston are notoriously known to be harsh, with ice and snow a staple for months, alongside gusty winds.”

You may have already heard about heavy snowfalls and the freezing temperatures, but there’s another thing that can get to you worse than the cold — the darkness. In December and January, the city of Boston gets an average of less than five hours of sunlight per day. If you’re visiting from farther up north or from Scandinavia, you’ll feel right at home!

city worker cleaning heavy snow on sidewalk in winter

Among other things that people appreciate about living in Boston are the food, the sports and the local culture. A small fraction feel that locals are impatient and reluctant to accept newcomers, but the overall sense you get when speaking to residents is one of pride. Bostonians don’t need others’ approval — they know their city has its ups and downs and they take criticisms on the chin. I’ll leave you with one last quote by local actress Lynn Julian from, that I think sums up this idea pretty well.

“Pro: you can say you’re from Boston, the best little city in the country.
Con: you say you’re from Bah-ston… and everyone laughs at your accent.”


George is a Real Estate Writer and Lifestyle Editor for Yardi, with a background in languages, marketing and YouTube content creation. He is now seeking to bring his love of detail and storytelling to the world of real estate. You can find him browsing Age of Sail books at your local bookstore, probably...

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