A Defense of Boston’s Coolness
If you’re from anywhere cool, Boston feels like the place you reluctantly ended up in. For sure, you can sip an overpriced pint at a walkable bar, but what is that worth if the bar has 6 TV screens playing every sport at once with the plainest crowd you’ve ever seen donning the greyest sweatshirts. The politics are good, but where does that get you when you’re easily the only person of color in most spaces you occupy. The economy is strong, but all the jobs are in biotech or tech-tech and everyone can’t seem to get enough of rock climbing. It's old and charming, but unaffordable and segregated. It’s pretty in the fall, but standoffish and stuck in time, defined by its fear of change along pristine avenues and boulevards. Boston is the city of dreams on paper, outperforming almost every quality-of-life metric1 to measure places in the US, but the criticisms of its coolness are real and heard often in passive conversation. Even a slight public confession of satisfaction with this city is met with a crowd of boos, making one (me) defensive and weird for secretly liking my experience here through its ups and downs. I grew up in Koreatown, Los Angeles, which, to be totally unbiased, is very cool. It's dense, diverse, affordable, and unique. Most importantly, it's not Boston, which is synonymous for even base level coolness. Either I’m actually really uncool or being gaslit, but this doesn’t feel fair, and Boston’s judgement deserves an exploration. Is Boston really that uncool? To whom is it cool? Can it become cool? Is coolness masked language for transplant satisfaction? Let’s talk about it!
To be clear, I think Boston is cool, but its coolness has been revealed to me through a process of discovery over many years. This discovery has largely been through meeting people and slowly gaining ownership of the city by interacting with it in unique and interesting ways. My work as an urban planner provided me the space for this ownership because I often found myself in positions where I had to hear Bostonians out on the future of their city and how they view themselves, gradually becoming part of their community. Bostonians love participating in their city and take a lot of pride in their urban imaginations, which is very cool. MBTA Board Meetings are a perfect place to witness this because they begin with a rambunctious public comment period where people of all identities yell at the board about what they want from the T and its importance to them. I attended these meetings as part of my job but really looked forward to public comments because of everyone’s investment in the success of the T. One consistent figure was (and is!) Louise Baxter, a member of the T riders union who came to almost every meeting I attended to talk about the importance of the system to her life, the city, and the climate. I have never talked to Louise, but learned a lot about her through these meetings, like how she’s a lifelong Boston resident and how she does not own a car and relies on the accessibility of the T as a senior citizen. She always took her time to speak about her values and wore several pins to proudly demonstrate her love for transit. Louise saw herself as powerful at these meetings and an owner of her (sometimes janky) transit system, which I think is unique to Boston and pretty inspiring (cool).
As part of this exploration of coolness, I had a sit-down conversation with Alula Hussen, a friend and editorial manager at the Boston Ujima Project, an organization that advocates and furthers cooperative ownership of business, arts, and culture for communities of color in Boston. Alula, like me, came here from somewhere else (Cleveland, Ohio) and when asked if Boston is cool, responded with a resounding “Hell Yea!” He approached finding Boston’s cool-factor with an exceptional degree of patience and has largely described it in the context of his community-oriented friends and through the creative spaces and events where he’s felt welcome. His story of discovery included his first basement show in Dorchester, which he ended with a “I didn’t think something like this existed here,” prompting me to tell a story about a jazz show I went to at a rowdy retirement home in Allston, ending it with the same sentiment. We agreed that, despite not having the density of activity found in cities like New York, the spirit of discovering “that cool thing” which speaks to you is alive and well in Boston. We both agreed that the process of our own discoveries was worth it as we were sitting outside The Buttery in the historic South End also discussing the complete gentrification of this formally Black and Puerto Rican neighborhood. In the same breath as our excitement for the city, we both landed on the fact that racism is not cool, and Boston has tons of it. When asked about how he reconciles being feeling racially excluded in Boston, or where he finds solace from the uncool, Alula discussed his community and work from the Cambridge Community Center to the Ujima Project. He named spots in Uphams Corner, Nubian Square, and Roxbury (I’m not giving them away), and hoped some of the ones that closed post-COVID come back. Alula, like Louise, doubled down on Boston and is actively making it cooler through his work (check some of it out here), proving that Boston can become cool past the cheap drink. We ended our conversation by talking about skateboarding and Jahmal Williams (a Boston skater) and made plans to skate spots on Saturday.
The first person that came to mind when I was embarking on this exploration was Sam Kaufman. As a Jamaica Plain native and self-proclaimed certified yapper, Sam will let you know how much cooler Boston is than New York or any other city. “I can’t have sun every day!” she said on our walk and yap session, discussing her recent summer in California. As a lover of seasons, I agreed while we dissected Boston’s coolness. As someone who grew up here and worked in the Massachusetts Executive Office for eight years, Sam has seen Boston through a lot of change, and despite being incredibly different from Alula, aligns with him in her love for people she’s found in this city. Sam credits the cultural institutions, the museums, and the universities for bringing unlikely and extraordinary folks together, really valuing the intellectualism of the city. Despite the nerdiness being too much at times, she thinks it's central to the city’s identity. Reflecting on the shifts in Boston’s coolness, Sam also reminisced about things lost through change and development. “The MFA at night was truly an all-night party,” but is now, she admits, much more inaccessible because it’s always sold out. “Garment District was a place you had to discover” she also stated, referring to the thrift store in Kendall when the neighborhood was just industrial buildings compared to today’s biotech hub. As a witness to change, Sam also discussed neighborhoods that are truly uncool, like the Seaport, filled with corporate architecture and luxury housing along with spots that were lost, like River Gods with its funky décor. It was clear through our conversation that gentrification had taken a toll on the coolness of Boston despite making it cleaner and safer. It had sanitized the city in many ways, displacing the artists and creatives who thrived on cheap rents and bad roads. Despite this, Sam could list a thousand things that were still cool, most focused on what isn’t displaced. Sam always came back to the vibe of the people, specifically those from here: not-nice but kind. When asked about her spots for solace, she focused inwards, discussing the localness and Boston’s vibe as “a city of neighborhoods.” Anyone who knows Sam knows that she’s a people person, even attracting folks on our walk for a quick chat or a dinner invite. Sam is real and so is Boston, which is cool. Best of all, “you don’t have to go to fucking Times Square.”
Both Sam and Alula see Boston’s coolness from a perspective of values, community, and keeping things local. Boston has changed (and lost) a lot over the past few decades due to displacement and America’s reemerging love for walkable cities. Despite the boom in land values, shadows of red-lining, the 1970s busing policy, and growing income-inequality loom over the city.
Unaffordability is a top concern and a significant barrier to accessible arts and culture, elements that seem to be important for coolness. The spirit of discovery is alive in Boston but it’s also essential because most spaces are heavily commodified and expensive. What is cool also has to be found (or kept safe). The cheap drink is not central to the cool city but, as Sam pointed out, it is a framework for general unaffordability. These concerns are real, but so are the people working everyday to create spaces and work on their communities despite the odds. Boston has tons of that, and it has Louise, Alula, and Sam, which makes it cool.
1. https://www.boston25news.com/news/local/massachusetts-ranked-best-place-live-america-2024/PXJEX3YSLBDXLNOACOI73SOSO4/#:~:text=BOSTON%20%E2%80%94%20Massachusetts%20has%20been%20ranked,according%20to%20a%20new%20study.