Could I Live There? Boston, and Its New England Charm

A new column celebrating the possibilities from Sheri Radel Rosenberg. Boston is a great city, but could Sheri live there?

Here at AGEIST, we embrace opportunities and celebrate aging on our terms. I created this column to reframe our comfort zone into something expansive and full of curiosity.

The following few pieces in this series will continue to examine place. And next up is a place I recently visited to see some friends. It’s the salt-of-the-earth yet Ivy-strewn city of Boston, birthplace of Ben Affleck, Aerosmith, and some wicked good seafood.

So, with an oyster shot in hand and Good Will Hunting in the background, here’s a  question.

Could I live there? (I’ve rephrased the question from here to there, and it’s better that way.)

As a proud Northeasterner, Boston checks out. It’s charming and brimming with a historical patina, and it has a blue-collar mixed with a blue-blood vibe that reminds me of my hometown of Philadelphia. The seafood tower game is strong, and the shopping is full of the usual suspects on upscale Newbury Street (from Hermès to H&M) and cute,  independent boutiques on quaint Charles Street in Beacon Hill. 

There is not a place I travel to that I don’t think about what it would be like to live there, in almost forensic detail. What would I do? What kind of shop would I open? What style of living and what neighborhood is most “us”? 

Though there are things to love about Boston, it’s not a town that I feel in tune with and, in fact, both David and I noticed that the way people walk through Boston is very different from how people walk in Brooklyn. On President’s Day weekend, the tourists were hard to take, and there were hoards of them, and the claustrophobia and blood pressure felt fairly high on the cobblestone, narrow streets.

On the plus side, Boston is a city full of athletes with tons of runners due to the iconic marathon culture. People seem reasonably fit despite the frigid winters, and New Balance is based in Beantown, as is Converse. The city is also extremely dog friendly and, if you are a sports fan, one word: Fenway. Oh, one more word: Celtics. And several more words: Bruins and Patriots. Boston is a notorious sports town; being a fan is a full-tilt obsession. 

Boston has a fabulous food scene

Also, Boston has a fabulous food scene; as mentioned, the seafood is fantastic. There is no shortage of Italian and Chinese food, two must-haves for a New York girl like me. The academic options are world-class. Boston is a great walking city (though it’s not grid-like so navigating on foot is a challenge for newbies), and the public transportation is quite good.  It is a big biking town with a bustling international airport and train service to the entire Northeast corridor, with Acela service to NYC in under four hours. Oh, and summers on the Cape are worth the price of admission. The Cape is pure magic, a place where you immediately summon an all-American Kennedy prep that is beyond iconic.

As far as where to live, the whole city has a small-town feel, which some might dig. Beacon Hill is all about old architecture, while nearby Newbury Street in the Back Bay feels posh and grand. There are up-and-coming neighborhoods like Brighton and Allston, though, admittedly, I couldn’t catch a vibe there. The area around Fenway feels good, and suburbs like Weston feel very old money and, at 15 minutes from the city, a wealthy, wooded oasis with multimillion-dollar homes.

According to Realtor.com, the median listing home price in Boston, MA was $849K, trending up 6.9% year-over-year as of January 2023. The median listing home price per square foot was $804, and the median home sold price was $727K. Boston, MA, is a seller’s market, which means there are more people looking to buy than homes available.

I have always loved a college town

But my two favorite areas are Cambridge and Wellesley, two college towns that are just great. Cambridge is famously home to Harvard, and it’s hard not to fall in love with one of the most beautiful campuses in the world. And Wellesley is in the burbs but close to the city, and it’s a charming town with good shopping and food. I have always loved a college town, and I find something about being on or near a campus inspiring and exciting. All of that mind-opening and futurescaping. How can you not love that?

But Love Story fantasies aside, reality bites. And my reality needs endless stimulation of the creative variety. Sure, Boston is a cultured city, but a lack of creative energy makes it fall flat for me. The museums and ballet and opera are excellent. But it’s more the feel of the air vs the fine arts. There’s a difference. I also didn’t spot a lot of diversity, and the city feels salty like Philly but also bland at the same time. 

The weather can be awful in the winter. And the overall vibe could be better. If New York is a vibey live wire, Boston found me looking for an outlet.

But since I have a wonderful friend living there and never met an old, drafty building I didn’t like, was Boston an option, or could it ever be?

The Verdict

Boston is liberal and academic and has incredible hospitals. Its New England countenance is appealing, as is its location on the lovely River Charles. Hanging at Harvard makes my heart sing, and there’s a brusqueness to the people familiar to my Philadelphia DNA.

But the lack of creative culture is a dealbreaker for me, as is the rather conservative style.  Case in point: I wore a velour/velvet Norma Kamali jumpsuit to dinner that made me feel cute, but my friend, who owns a consignment business in Weston, said it “would be considered weird here.” If a girl can’t wear a jumpsuit as a ubiquitous wardrobe staple without judgment, this is a problem. In short, not my vibe and not an option. I am all about vibes, and Boston is a vibe I don’t feel. It lacks “edge,” and I need a bit of edge with my everyday coffee. Don’t even get me started on the traffic and the super sketchy driving. 

It must be that small-town thing that, though a plus to some, is a minus for me. Friedrich Engels said, “Boston is just a village, sprawling far and wide, more human than New York City.” 

Perhaps that’s true for some humans, but not this one. Speaking of everyday coffee, I love Dunkin’ Donuts, but I can get a latte light in Brooklyn, so I’m stayin’. 

Talk to me in the comments.  XO

See medical disclaimer below. ↓


  1. My jaw dropped and I mouthed an exaggerated “WHAT” when I read your friend’s comment about your Norma Kamali jumpsuit!

    My daughter is a Junior at Berklee College of Music, so I have spent time in Boston. I agree with your assessment and am counting down the months til she graduates.

    I guess you haven’t parked in an alley on a sliver of asphalt? SpotHero’s Customer Service had to talk me through finding that affordable parking spot😂

    • Amen. Thanks for reading. My father’s brother was a concert violinist and studied there and then later moved to New Orleans, a city that has always had me smitten.

  2. I must state up front that I am a Massachusetts resident, although I live in a small town and have never lived in Boston. I will also state that in the past and for 26 years (1978-2004)I lived in various neighborhoods (Clinton Hill, Kings Highway, Park Slope, and Carroll Gardens) in Brooklyn and am no longer a “city” guy. I think that it is very difficult to form a solid opinion about a place on such a short stay. I also think that one would have to visit several times at different times of year to determine the “vibe” of a place. You can get a partial read, but not a well informed one. I do not know what this sentence means as related to the arts: “But it’s more the feel of the air vs the fine arts.”

    As a former Brooklynite, I was proud to live there, but always thought that some of Brooklyn’s greatness owed a lot to its proximity to Manhattan. Of course Brooklyn changed dramatically from 1978 to 2004, and has changed much more since. Unfortunately, much of its wonderful grittiness and urban post-industrial atmosphere has been supplanted by places like Ikea, and others that serve latte light.

  3. Hi, Mike. Thanks for reading. I have been to Boston many times, and at different times of year. What I meant by the “air” comment is that I like a creative vibe in the air vs. attending the opera or the ballet. I like to be inspired by what people are doing and wearing on the street, if that makes sense. Completely disagree about your first thoughts on Brooklyn. It has its own vibe and true there’s Ikea here, but there’s also still a lovely, leafy feel in my neighborhood (Carroll Gardens) that is hard to beat. Stay tuned to read more about that soon and thanks again for your thoughts. Small town Mass sounds mighty good, ps. Ya never know.

    • sheri. I was a long time Carroll Gardens resident and lived on the top floor of a large brownstone with skyline views on First Place between Court and Clinton. The neighbor that lived below me, Anna, had lived there since 1930. It was a great apartment for a number of reasons, and the way I found it was a classic Brooklyn story that is too long to tell here. I would not be able to afford that apartment these days. New York profoundly effected my life path as I went to design school in Brooklyn, was a long-time designer in the city, and met my wife there along the journey.

      I am sure Brooklyn has its own vibe, and It will always be a part of me, but I was talking about the aspects of Brooklyn that have disappeared in the last 20 years, specifically its rich industrial coastline. I was a sponge when exploring or traveling anywhere in the city soaking up its textures, patina, and visual richness, especially old industrial landscapes. I used to explore abandoned power plants, the former Domino sugar refinery in Williamsburg (which I visited legally when it was still in operation), the sculptural sugar refinery and dry docks in Red Hook, various bridge towers and anchorages, and Industry City before it was repurposed. There is nothing wrong with what has happened at Industry City. In fact it has brought the neighborhood to life and is a great reuse story for those long underused buildings. Of course I know little of what is going on in Brooklyn nowadays as I have not lived there for almost 20 years. Change is the only constant in NYC or anywhere for that matter. My next and hopefully last stop will be the Connecticut coast.

      Your post is about Boston and here I am prattling on about Brooklyn.

      • Ha you can’t take the BK outta the boy! Love this comment. So glad you have such wonderful memories of this cuckoo place. PS what’s a Connecticut? 🤭

        • I am a museum exhibit designer focusing on historical exhibits, and have designed a few projects located near the Mystic, Connecticut area. I have loved the area for a long time, and a couple of years ago we purchased a modern house located on a large treed lot on the Mystic River. If all goes well we will move there full time in a year or so. Right now we rent it out on Airbnb.

          • That sounds amazing. What a wonderful journey. We were planning on stopping in Mystic on the way back but decided to stay a bit longer in Boston/Cambridge. You may have to do a dispatch from there when you move!

  4. My son went to Harvard so I got to spend some time there – in the nice weather. Cambridge is lovely as is the Charles River, but like you never yearned to live there and lord knows I’ve lived everywhere. I did hitch hike from Boston to western MA in the seventies and got a ride from a very nice truck driver. Good college town but on to NYC!!!

      • It was NYC in my twenties! What a time I had from museums, running up the East River after work, preview theater seats, a boyfrind with a brown convertible Porsche, getting a date every time I walked out the door, meeting my husband in the middle of Central Park, all night poetry reading at St Marks cathedral in the Village and walking home at 3 a.m., working at Meredith publishing and broadcasting for Howard, biking up Madison Ave with my Golden Retriever Jonah behind me….it never ended. Living above a restaurant on 54th between 1st and 2nd….the time of my life.

  5. Hi Sheri
    Totally agree with your assessment, especially on the art front. Food is fab, and love to visit, but not somewhere I want to live.

    I am loving these articles and look forward to reading them.


  6. WESTON??? The wealthiest, whitest suburb in metrowest Boston. No one who lives here thinks WESTON has a “vibe.” Weston isn’t Boston… Do your homework, Sheri.

  7. I was staying in Beacon Hill. My friend lives in Weston. The aforementioned vibe was about the city, not Weston. Thanks for reading.

  8. beacon Hill…but no mention of the Museum of African American History..?? Great programming there… Jamaica Plain?? Darryl’s Corner Bar?

  9. Thank you for your comments on Boston – I have only visited there but agree that I would not want to live there – too programmed for me. This comment is more for the comment preceding me – tell me – why is it so necessary to criticize so much?

  10. I’m a native New Yorker and haven’t visited Boston in about 25 years. But your assessment matches my impression of the city from my last visit. Nice but bland. No street energy. No thanks.

  11. In the 3 yrs we lived there, I rarely saw anyone dressing with pizazz…winter downtown was a sea of long grey, navy and black coats. We lived in Southie to save $ and loved Fort Point arts district and also the vibe of Jamaica Plain. At the time (early 2000s) there was a budding tech-art scene in cambridge that piqued my interest. But ultimately, we were glad to move and haven’t been back

  12. Sheri-
    I cannot wait for every opinion of every city you visit. I love how honest, funny and thorough you are using the lens of a New Yorker. You were respectful to Boston but carefully explained what was missing to make your heart beat faster. I get it. Where to next?

  13. A city like New Orleans has you smitten?!?! You must love the out of control crime. Hope you enjoy the “creativity”…
    You clearly aren’t sophisticated enough for my city.

    • I just happen to love New Orleans for its soulful, lively people, wonderful music and food, and European feel. If that’s unsophisticated, sue me. Also, I live in one of the most sophisticated cities in the world, so that comment feels a bit off. I do appreciate you reading but we all are allowed to like what we like and love what we love.


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The ideas expressed here are solely the opinions of the author and are not researched or verified by AGEIST LLC, or anyone associated with AGEIST LLC. This material should not be construed as medical advice or recommendation, it is for informational use only. We encourage all readers to discuss with your qualified practitioners the relevance of the application of any of these ideas to your life. The recommendations contained herein are not intended to diagnose, treat, cure or prevent any disease. You should always consult your physician or other qualified health provider before starting any new treatment or stopping any treatment that has been prescribed for you by your physician or other qualified health provider. Please call your doctor or 911 immediately if you think you may have a medical or psychiatric emergency.

Sheri Radel Rosenberghttps://unapologeticstyle.substack.com/
Sheri Radel Rosenberg is a Philly-born, Brooklyn-based writer who explores style, beauty, culture, and midlife with wit, warmth, and wisdom. Her story includes successful forays in the worlds of trend forecasting, ad agency photo production, ghostwriting, and strategic messaging development for fashion and beauty brands - all while amassing a slip dress collection that would make any Gen Xer proud. At the dawn of social media, Sheri launched her personal blog–which combines her passion for writing with her style obsession–and she hasn’t looked back. As Style Editor for the AGEIST, she’s inspired by the styles of the 70s and the 90s, along with all the beautiful people she sees daily in NYC.


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