Don't Move to Boston

Don’t Move to Boston, Massachusetts

So you are thinking about moving to Boston. Well wait just a moment… It may not be all that it is cracked up to be! It's hard to believe, but there are some negatives to this world class city. Especially if you are coming from an area that is not as…. We will go with prestigious!

Take it from me as I was not born and raised here… There is a little bit of a culture shock, so I want you to know some of the negatives of our fair city ahead of time. This way you can be well prepared!

Hey, it’s Jeff Chubb. I am a recovering investment banker turned real estate agent that has sold more than a 1,000 (One Thousand) homes and am one of the top agents in the state of Massachusetts. If you have any real estate questions, then I look forward to being your resource for answers.

As I mentioned, I will be covering some of the most negative items about moving to Boston and I will tell you what… There are some good ones in here. But we are going to start out with the Weather of course.

Weather: You say you are from Boston to someone in pretty much any area that is South of us… And they look back at you with puppy dog sorrowful eyes saying something along the lines of, “oh, it’s cold up there”. We have these things called the seasons in Boston. We get them all. Spring, Summer, Fall and the yes… the Winter. There are some days that you will wake up and leave the house in a jacket to only be wishing you had shorts on by the afternoon and to then be complaining how cold it is by dinner time… But then there are the days that are just pure perfection.

Yes. We get snow. No, it’s not as much as you think. It’s true. Some years are worse than others, Personally, I like the snow. Not the 10 feet of snow and I can’t stand the 1-inch snowstorms... But it’s pretty and it can be fun.

Plus, without experiencing the bad… Can you really appreciate the good? Maybe that is why our summers are so darn awesome.

Expense. Boston is not cheap. It’s true. But is any world class city affordable? I remember moving from New York City to Boston and thinking “WOW, what a great value Boston is!”. It really is all relative because if I had come straight from where I grew up in which is Delaware to Boston… Then I think I would have had a minor heart attack.

As a whole, we are definitely more expensive, but there are areas that offer people more affordability than others.

It’s like everything else in life… If you want the best, then it’s going to cost you. You don’t walk into a Ferrari dealership expecting to pay Ford prices. And yes, I am saying that Boston is the Ferrari of a city… Especially compared to the second-rate city located a little South of us!

Density: Being able to stretch out may not be that easy in Boston… However, some neighborhoods may be easier then others. Boston has a density of 13,841 people per square mile. Greater Boston is the 4th most densely populated region in the United States after New York Metro Area, Los Angeles Metro Area and South Florida Metro Area.  

When it comes to the actual population of Boston, it’s not as big as most people think. The population of Boston is about 700,000 people as the city itself is only 48 square miles. Some neighborhoods like West Roxbury are going to be FAR less dense then compared to some of Boston’s most dense neighborhoods like Allston and Brighton.

Traffic: Boston traffic is bad enough to make a grown man cry. Daily. In 2020 we were blessed with the “worst traffic in the US” title… Again. Drivers in Boston lost 149 hours in 2019 due to traffic congestion. If I hated myself… Then this may be a stat that I would start to keep track of.

Then Covid happened. And now traffic is back, but the patterns have changed. Traffic is back to 2019 levels, but it seems that it has improved in some areas with some commute times improving. It seems that people are not working the traditional 9 to 5 day.

To speak frankly… Even with the “improvements”, it still SUCKS. 93 is one of the worst roads in America. Whether you are going North or South… it’s gonna get you and own you. And the Mass Pike is no dream either. Which leads to Mass transit as an option… But don’t get so excited as Mass Transit is on this list as well.

Driving & Parking:  For those that are thinking that this is one of the same as Traffic and that I am beating a dead horse… Oh no. Patience is more then a virtue if you are driving in Boston. You want to drive Boston without a GPS… Forget about it. Cities that work in grids make a lot of sense… Boston does not work on a grid. Then there are the constant detours to just screw with you some more.

THEN on top of it… Boston has decided to get rid of a lot of driving lanes throughout the city in order to give bikers their own special parking lane. This preference to bikers has only helped make traffic worse and decrease the amount of parking…. And oh yes. Parking. It’s cutthroat.

Quick story. I am not originally from here. My first house was in East Boston. I got home around 1 or 2am about a week and a half after a snowstorm. There was no parking except for a “marked” spot. This spot was marked with a cinder block and a 2x4. It had been over a week and a half since this storm happened. I moved them. And then woke up to that cinder block thrown on the hood of my car.

Parking is cutthroat. Some neighborhoods are worse than others. But it is a city. Parking is a premium.

Mass Transportation: I have already talked about how traffic sucks… So that must mean that our Mass Transit city is awesome, right? How do I describe Boston’s mass transit? It’s like a drunk guy took some of his kids crayons and started drawing some lines in different colors on a map of Boston. A red, green, orange, blue and purple crayon to be exact.

Let’s start with the purple line. This is the Commuter Rail. Now I know what you are thinking. There must be a central spot where the lines in the North, South and West all come together. And that you could ride a train from the Northern spot in Massachusetts down to the most Southern spot in Massachusetts. That would make sense… And because it makes sense, then that means that isn’t the case. The north commuter lines arrive in to Boston at North Station. Meanwhile the West, Southern and Amtrak lines meet up at South Station.

Now lets move to the oldest subway in North America. That would be the Green line. This is the line where that drunk guy really found his creative streak. The green line breaks off at the Copley stop with the E line going one way and the B, C and D line going straight out towards the West. THEN at the Kenmore stop, the B, C and D line goes their separate ways throughout Boston and through Brookline. The are currently extending the Green line throughout Somerville… And no, that is not the A line. It is an extension of the E line.

The Red line goes from Cambridge through Boston down to Braintree. While the Orange line goes from Roslindale up through Malden. Then there is the Blue Line. The Blue line starts in Beacon Hill and goes through Revere.

Oh ya, then there is the Silver Line. Sorry, I kind of consider this a joke line because it is a bus. There are buses all throughout Boston so I still don’t get it. But the Silver line goes throughout Roxbury, Seaport District, the Airport and up to Chelsea. But it’s a bus…

It is okay to be confused. I am pretty sure it’s by design.

Taxes: Welcome to Taxachusetts. I actually think that is a little unfair. I think it is really Feeachusetts with a little higher tax rate thrown into the mix. This negative really doesn’t fall on the city of Boston though… They are actually pretty great when it comes to taxes. There is no separate city tax like they have in New York City. And I have to say that their property tax rate is reasonable. 

Reputation for unfriendliness: Recently Business Insider ranked Boston as the fifth rudest city in the nation. I think Bostonians would be pretty insulted at this ranking… We strive to be first at everything! It seems New York, LA, Washington D.C and Chicago beat us out. Chicago, really?

At the end of the day, 14.9% of respondents said Boston. I mean we have aggressive driving, bad traffic, will go to fists over parking and have a rabid sports fandom that we will shortly talk about. A Bostonian is not afraid to hold back and tell it like it is… Someone who is accustomed to being a Keyboard warrior could find a different fate here in the Bay State.

What many in the nation don’t understand is that when you call us a “Masshole”, the typical born and bread will say “hell yeah”… Actually they won’t say hell. I am just trying to keep this PG-13. But I will tell you this… The buttoned-up culture begins to grow on you. Then all of a sudden you will find yourself dropping a wicked in a sentence and before you know it… You are calling a sub a hoagie and the shoulder a breakdown lane. And for the record… It’s not about being unfriendly. It’s about being reserved. But in the end… We all have a certain love and are die hard for one another.

I will say… People not holding the door for one another still drives me up the wall.

Very “Neighborhoody”:

Boston is a city. But there are a lot of neighborhoods that make up that city. I actually did a video breaking down all the neighborhoods which I will have at the end of the video. Definitely worth a watch.

The neighborhoody stature can get annoying, but it is also great. There are those that seem to never make it out of their neighborhood as many have all they need. But the best part is that there is literally a neighborhood for everyone. And some neighborhoods are more pigeon holed then others.

Example? Allston and Brighton are known for the college folk. Southie used be known as the Irish section of town, but has now been taken over by young professionals. The South End used to have a big gay community, but that community is starting to migrate over to Dorchester. At this point I don’t know if you can find any Italians living in the North End… Just their food!

It’s not about THE neighborhood though. It’s about YOU. What is important to you? Because at the end of the day, I promise you will be able to find your little enclave and most likely you may just begin to love the neighborhoody feeling.

Love their sport teams: This one is great if you happen to love the same sports teams. If you love the Pats, Bruins, Celtics and Sox then you are going to make a lot of friends real fast.

If you have any other allegiance to another sub tiered sports team, then Bostonians may just look at you a little more cautiously from the onset.

I can remember many years ago someone pelting me with a snowball as I was walking away from the bar with my hometown jersey on… The buddy I was walking with recommended that I don’t look back and keep on going.

Here is the thing… This has really been toned down a lot in the last couple decades. Bostonians refer to their city as Titletown… And it has been a pretty incredible couple decades. With all the good times, they have become tamer… And in their defense. The curse of the Bambino was not an easy 86 years for fans.

If you love passion. If you love being around a diehard culture. Then you will love Boston.

No Happy Hour & Lackluster Night Life: I spent a couple years working for an investment bank in New York and then moved to Boston. I got a taste for both of social scenes at a time that my Liver was in tip top shape.

I remember us leaving our apartments at 11am in New York City. Bars closed at 4am. In Boston bars either close at 1 or 2am. As I have gotten older, I will say with certainty that nothing good ever happens after 2am! As an old man, Boston wins there. But the cover charges and lines drove me up the wall in Boston. I don’t remember standing in line or paying a cover charge to get in a bar.

Side bar, but cover charges always drove me up the wall. You mean I am paying to go into a place where I am only going to be paying you a lot more?!?  For the most part, Boston is not known for their night life, but I can tell you with certainty and experience that it is better then Delaware. So, depending on where you are coming from... All things are relative.

Schools: Massachusetts is considered to have the best Public School System in the country. However the Boston School system as a whole is not considered as one of the best. I say as a whole, because Boston does have a couple schools that do achieve high national standings. Boston Latin School ranks #26 in the NATION. It is also the oldest public school in the United States. Currently they have redone how kids are admitted into this top school. 20% of an incoming class is accepted based on top grades and the other 80% are based on grades and zip codes with students from zip codes in lower-income communities receiving preferential treatment.

As a whole, the Boston School System enrolls nearly 50,000 students in grades of Pre-Kindergarten through 12th. They have a student to teacher ratio of 10 to 1 with a graduation rate of 73%. According to, the district ranks in the bottom 50%. Their math proficiency is 35% compared to a Massachusetts Public School average of 51% while their reading proficiency score is 37% compared to the Massachusetts average of 54%.

That is a wrap on this video as to what I consider the biggest downsides of moving to Boston. It’s really important to remember that just like any place… There will always be some negatives.

Yes, these are the negatives. But when you start adding in all the positives, then that is where you will see it all balance out and quickly take the lead! Boston is an incredible place to live. I lived in many places in my life… And Boston by far has been the best.

It’s a city that acts like a town. It can be as big or as small as you like. Many of the things I just talked about is pretty much city life no matter what city you live in. If the city isn’t for you, then we have some really incredible towns right outside of the city. Including many towns that are located right on the Massachusetts coastline.

This was all things to mention so that you could keep them in mind, but none of this is unmanageable. Frankly. Our city is awesome.

I hope you found some value in this video. Whether you are moving in 9 days or 90, be sure to give me a call or shoot me an email. All of my contact information is in the description below. I would love to meet you and get to know you a bit better and talk more about your goals.

Let me know if you have any questions and until next time!

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