Why I’m moving to Portland, Maine

Old Port, Portland, Maine. Photo by Jeff Gunn.

Yesterday my wife and I bought a house in Portland, Maine. We’ll be moving there soon.

I thought you might be interested in how we chose Portland, after 40 years of living near Boston.

Why New England?

I moved to New England — Cambridge, Massachusetts — in 1979 at age 20 and I’ve been here ever since. That’s basically my whole adult life.

During that time, I developed an affinity for New England. As my career developed, I thought it might be advantageous to move to Silicon Valley, but when I proposed that move to my wife, she said “Well, I’ll miss you.” That was too high a price for me, and in all this time in the suburbs of Boston I’ve put down roots and made friends.

Even though I’ve lived near Boston, my connection is to the whole region. In contrast to bigger states like Pennsylvania or California, in the New England states all of us share a connection. We’re all (or almost all) Red Sox and Celtics fans. We share a respect for the winter snow and the beaches on Cape Cod and The Islands. With a due nod to Yale, we know Harvard is the center of the academic universe, and education is important to us. We’re hardy and hard workers. We’re not all liberal, but a lot of us are.

Boston (metro area population 4.6 million) is the hub that the whole region revolves around — nobody would seriously attempt to put Hartford (1.2 million) or Providence (1.6 million) in that role. We read the Boston papers, mostly the Boston Globe, and we all have friends across state lines.

At this point in our lives, my wife and I didn’t even need to talk about it. We knew we’d end up in New England somewhere, because we needed to be close enough to see our friends and family here — we have two kids now living in central Massachusetts.

But where?

Why Maine?

Here’s a series of completely unfair thumbnail impressions of the New England states.

Connecticut lost any appeal it might have had for me based on my memories of unpleasant visits with my in-laws from my first marriage in West Hartford. My impressions of Connecticut are of a state with a bunch of rich New York suburbs at one end and an insurance-industry-dominated city in the middle. I’m sure that’s not fair, but there was no way we were going to end up in Connecticut.

Rhode Island is just what you’d expect — too small. There’s nothing there to draw me in. In any case, I believe global warming is real — it’s getting hotter, and I wasn’t going to live in “The Ocean State.” This meant that we wanted to live in a place that’s not too hot, and not all on the seacoast: Vermont, New Hampshire, Massachusetts, or Maine.

Vermont is too rugged and rural. The biggest city is Burlington at just 43,000 people and there are only 600,000 people in the whole state. We considered it, but wanted to be closer to a more urban environment. Burlington is on Lake Champlain, but Vermont has no seacoast, and we wanted to be somewhere near the ocean.

New Hampshire is known for being flinty, with low taxes and a stingy government. We wanted better services than that, and didn’t want to be part of the once-every-four-years circus that is the New Hampshire presidential primary. New Hampshire also has only the tiniest sliver of seacoast.

Massachusetts still held some appeal, and we considered moving west to the Berkshires portion of the state. There were three reasons we didn’t — first, we were ready to try something different; second, we wanted to give our kids some breathing space; and third, Maine sucked us in first.

As for Maine, people from outside the state often take their impressions from Stephen King novels about small and insular towns. But Maine is the biggest state in New England by land area, and it has everything — a rocky seacoast, lots of beaches, impressive mountains, and Portland, a small but amazing city only two hours from Boston. Its politics is mixed, split between the left-leaning southeastern coast and the vast rural parts of the state.

Mainers certainly aren’t warm and friendly on the surface like lots of people in the South, but I’ve always found them to be willing to give you a fair shake if you give them a chance.

We also had some connections to the state. My wife had been coming to Maine since she was a child to visit her grandparents and uncle. And her mother lived in Freeport, Maine, for a long while in her retirement until she died a few years ago, which meant a lot of fond memories of our family visiting her up there. Maine sure isn’t Boston, but I grew to love it.

Why Portland?

Portland, Maine, is an amazing place.

Portland is the biggest city in Maine, but only has 67,000 people. Into that small city is packed a lot of culture and diversity. The Old Port district is bustling with creative activity, including art galleries and diverse restaurants. There’s plenty of access to big retailers, but most of it is tucked away in South Portland rather than spreading through the whole city. There are lots of suburban neighborhoods, but they’re very close to the small city. It has a farmer’s market that’s been going since 1768.

It’s 15 minutes to the small but well-connected airport, and from there you can go anywhere. (It will actually be faster to jet to see my parents in the Philadelphia area than it used to be when I lived in the Boston suburbs and had to deal with the congestion getting to and through Boston’s Logan Airport.) Staring from my house in Portland, I can be in New York City two hours after I set foot out my front door.

Portland is close to a bunch of awesome things. The ocean beaches are close by, but so are beautiful mountains.We can be back to see our friends in Boston or visit the theaters and culture in Boston in a couple hours. Acadia National Park is three hours away. Quebec City and Montreal are five hours away, and on a fast ferry, Halifax is just three and half hours travel.

The neighborhood we chose is ten minutes from a beautiful nature preserve on the Presumpscot river. But it seemed like everywhere in Portland is close to a green space or a beach.

If you want to be near the coast, the beach towns south of Portland are swollen with tourists in the summer, and we didn’t want to deal with that. Portland doesn’t get that big seasonal surge. North of Portland it thins out, and while there are are cute spots like Freeport (home of L.L. Bean and a hundred retail outlets) and Brunswick (home of Bowdoin college), you begin to get too far from anything that could properly be called a city. Inland is mostly pretty rural, and while we looked at some houses there, we didn’t want to be at the end of a dirt road and far from the services and health-care of a decent-sized city.

All of this somehow doesn’t get to what really matters, though. We just feel comfortable with this new place. It’s going to be fun to explore, but it feels like home. And since I’m shading into retirement, it’s going to be our home for quite a while.

15 responses to “Why I’m moving to Portland, Maine

  1. Portland is also a great town for dining out. That’s another huge bonus, to me at least. Good luck with your move!

  2. You forgot to mention all the lakes! I visited Moosehead Lake once, and that area is stunning. Thank you for sharing your decision process and realization that a finding a place that feels like home is the most important criteria of all!

  3. I would have never guessed the population of Maine or that Portland contributes so little of it. Keep us updated on your adventures.

  4. Welcome to Maine. I live in Kittery, but love to visit Portland, often when heading downeast for a visit to rural oceanfront. Maine is a big place. You’ll find that an awful lot of Mainers think Portland and south is not really Maine, but an extension of the Massahampshire seacoast. Portland is no Boston; too small, not enough academia. But it’s diverse (at least for Maine) and friendly. And it has Otto’s Pizza.

  5. Thanks for the explanation. I’ve visited Portland a couple of times when living in Salem, MA. I am considering moving to the Portland area, and have these questions:
    1. I would be looking to settle down and have a family – how open are local families to outsiders? Or are there enough transplants in the Portland area?
    2. What is the work/life culture of Portland like? As a native midwesterner, the culture here is focused on working hard. I am wondering if the culture in Portland is a little more focused on enjoying leisure time?
    3. Where do you find yourself traveling or exploring during weekends?

  6. Having vacationed in Portland right before the pandemic, and having lived in Houston since 2014, I absolutely fell in love with the city. I’ve encouraged my high school senior to apply to University of Southern Maine, and I 100% plan to move there once my last kiddo graduates. There’s something cozy and happy about the place, and you’re right about the political mix of people. I find that comforting. Thanks for the great run down of your reasons!

  7. Great info! We’re contemplating moving to Portland from Phoenix next summer, if all stars align. My wife is a dentist and visited there for a job interview before the pandemic. I’ve worked in juvenile probation/corrections since 2009. We’re starting to look for job leads. If anyone can point us in the right direction or if you have any contacts that we can network with, we’d certainly appreciate it!

    1. Hi Bryan,

      We live in Phoenix too and are so tired of the heat, traffic, bad air quality etc. We haven’t visited yet but I’ve been reading about the state like crazy. My husband is an attorney and we have a 2 year old. I’m a little worried about the winters. Please keep me informed of your progress! Mavis.enders@gmail.com

  8. Well,you moved into Portland and after 45 years of living there we moved out. The politics, cost of living the difficulty on getting from A to B, the.declining quantity and quality of services, the homeless problem. Open drug usage, the focus of City Hall on catering to the tourist industry at the expense of the neighborhoods, the rapidly declining school system cramming Woke indoctrination down the throats of the kids,….I am just warming up.
    Years ago it was a great place to live. We moved there in 1973, raised two kids there, and back then the school system was excellent. Our kids went on to earn advanced degrees and, like so many of Maine’s young people they moved away. We used to go to the Old Port, have a beer or three at Bull Feeney’s, catch h a ball game at Hadlock Field, and enjoy being out. Now when you go out you have st stop over some idiot lying on the doorstep strung out on dope, or run the gauntlet trying to get into the post office. Deering Oaks once was a gem…we would bring the kids there to enjoy the park. No more…it is too dangerous. Get the picture? So we sold out and moved to Florida. And we love it. Sure, there are some issues here, but we just got sick of the BS about Portland. And that is No Bullshiit.


    Robert Smith

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.