The Embrace, Boston Common © Aleney de Winter
An open letter to Boston, a city where cobblestones, cannoli and chance encounters spark a special kind of romance.
Dear Boston,
Well, this is a little awkward.
You see, I came to you with absolutely no expectations beyond a bit of history, a quiet museum and maybe a hot bowl of chowder. And thank you, you gave me all that, and then some.
But I have to tell you something, and I’ve been going back and forth about saying it, mostly because I didn’t want to come off as, you know… weird. I’m not, I swear. It’s just…. well, I’ve spent months mentally formulating what to say, like I’m in some painfully earnest rom-com where I blurt out a rehearsed confession and it’s awkward and cute and you laugh and everything fades to soft focus…
But real life is less Nora Ephron-coded. So here I am, Boston, and I’m just going to tell you straight… because I know you appreciate that kind of thing.
I am completely, head-over-sensible-walking-shoes-smitten with you.
So I’ve skipped the soft launch and went straight for the hard reveal. But please don’t run. I’m basically harmless… more the awkwardly waving from across the street type than crazed stalker.
So how did we get here? Let’s rewind a bit.
I was warned about you. Your stubborn charm, your mix of grit and grace and the way you cling to your revolutionary past while sprinting towards the future with a raised middle finger.
Historic? Undeniably. Smart? Wicked smaht, but also “a little… scrappy,” I was told by a friend who pointed to the Boston Tea Party as Exhibit A. Because, let’s be honest, it did involve grown men hurling crates of perfectly good tea into a harbour. Not exactly a masterclass in chill. But drawn as I am to the mature, the unpredictable and the occasionally ornery, my curiosity was aroused.
“You’ll probably get yelled at in the street. Probably by someone double-parked and waving a Dunkin’ Donut,” added my friend. And sure, that happened before I’d even left the airport, though minus the Dunkin’… probably due to the late hour. There I was, fresh off the plane, muttering to myself about airline delays or the structural integrity of my suitcase zipper or something, when another taxi cut in front of mine and, well, a shouty exchange ensued… you know how these things go. But those creative Boston-flavoured swears? Pure poetry.
Anyway, bug-eyed and running on fumes, it was close to midnight by the time I finally collapsed into the Lenox Hotel, a quietly brooding beauty tucked into Back Bay. All velvet chairs and dim lighting, as if someone’s eccentric but tasteful aunt had designed the place while marinating herself in whisky. Even at the late hour, a fireplace crackled in the lobby. The whole scene was so darkly atmospheric that I half expected Vincent Price to emerge from behind the concierge desk. Instead, a kindly young gentleman sorted out my keys and made sure a warm bowl of clam chowder and a glass of red followed me to my room. Smooth move.
Waking up to you, I sauntered down Commonwealth Avenue, your glorious brownstones flirting with me the whole way to the Boston Public Garden. By the time I hit the lagoon, resplendent with swan boats and surrounded by cherry blossoms that I swear literally threw themselves in my path like confetti (man, your game was cranked to eleven that morning), I just had to just stop and soak you in.
First impression? You’re really quite a looker. Like, seriously gaw-juss. The second? Your squirrels are suss! I watched, intrigued, as three of them, in full mobster mode, conducted what looked like a turf dispute. Not wanting to stick around and become a witness to whatever shady squirrel business was going down, I followed the crowd to Boston Common. And that’s when I found things starting to become a little, well, unusual.
I’d been expecting the usual urban park experiennce… joggers, squealing kids, someone loudly dissecting their rat-bahstahd ex on speakerphone. Instead, just beyond all the green, I stumbled into an outdoor museum of mortality .
Most cities try to impress first-time visitors with their greatest hits album. “Look at our famous bridge!” “Admire our iconic skyline!” You, though? You open with graveyards. Actual graveyards. Where other cities hide their dead like shameful secrets, you plonk them right there in the centre of everything. Weather-beaten old burial grounds where people walk their golden retrievers and eat breakfast next to lichen-clad tombstones that lean and squint like old men in a pub. It was a little unexpected, but also disarmingly charming.
Still, you played it cool at first. Gave me history before heart. Revolutionary War. Founding Fathers. The Freedom Trail. But then you snuck in those cobbled alleys in the North End that looked like they came straight from a historic fanfic. All wrought-iron fences, crooked bricks and windows I wanted to be on the other side of, gazing longingly to the street, as if the Bostonian equivalent of Mr Darcy might roll up in a Red Sox cap, hand me the keys to his brownstone and slip me a cannoli.
There was no Darcy. But there was a chap called Vinny, who told me with conviction that “Mike’s has the best cannoli. Don’t listen to no one else,” before mumbling something along the lines of showing me where Paul Revere took his last leak. Honestly, he was bang on about the cannoli, though I politely passed on the tour.
You went straight for the jugular with Isabella Stewart Gardner. The woman who built a Venetian palazzo in the middle of Boston to fill with art because she could. She’s been dead for over a century, and she’s still one of the coolest people in town. The way you still let her ghost run that palazzo, which is now a museum, exactly as she wanted, the artworks left exactly where she put them, and the empty frames of long-stolen paintings still hanging there like gorgeous, expensive wounds. I swooned. Literally swooned.
You’re a creative type, Boston, and you know that leaves me weak at the knees. Your Museum of Fine Arts is packed with masterpieces that hit me right in the feels. And the Institute of Contemporary Art refused to let me fake my way through as if I actually understood conceptual art. Spoiler alert… I don’t. But where most museums let me wander around, making thoughtful humming noises at stuff that could be profound or just expensive, yours demanded actual engagement and thought. Honestly, it was a bit like cerebral foreplay.
Then you threw in the SoWa Arts District, edgy and alternative but somehow still perfectly organised, like Brooklyn curated by someone’s very efficient mother. The galleries are legitimately brilliant, though, and the art? Be still, my heart.
But we really started to get to know each other over a string of meet-cute-worthy meals. Those lobster rolls so indecently buttery I thought about them for days. That candlelit dinner at Woods Hill Pier 4. A romantic soiree at the public library, all carefully crafted sandwiches, pretty cakes and scones smothered in cream and lemon curd. The almond croissants from Tatte Bakery, which are so good I’m fairly sure they are responsible for the city’s emotional wellbeing. Cannoli… from Mike’s, of course (thanks, Vinny). And then the Union Oyster House, where they’ve been slinging chowder and oysters for over 200 years, in a building that was standing before my own country was even a twinkle in a coloniser’s eye. I ordered both, obviously, and briefly considered quitting my day job to write sonnets about shellfish.
I have to mention your Red Sox. I never made it to a game, but one evening I stepped off the T and got swallowed by a crowd of jerseys, chants and faces flushed with beer and tribal pride. It moved as one, like a friendly invasion force in matching jerseys. At one point, someone shoved a foam finger at me as if I were part of this loveable, loud and slightly crazy family. I kind of wished I was.
But I have to make a confession. I did cheat on you. Only a little. A side fling. With Salem. A brief affair involving broomsticks and salt air. But even then, I was thinking about you. Sure, Salem had witches, whimsy and lantern-lit taverns that turned my head, but I couldn’t help picturing you rolling your eyes at the drama and dress-ups. Then handing me a well-footnoted book with a wink, like, “Here’s what actually happened. in Salem.” So pragmatic. So smart. So… Boston.
I returned to your streets and everything already felt familiar, even after only a few days. I knew where to find good coffee. I was on first-name terms with the staff at a local bookshop. I even had a favourite bench. (Still didn’t trust the squirrels though. Shifty little guys. Way too cocky for something that fluffy.)
And that’s when it hit me. I was in deep.
I wasn’t supposed to fall for you. I was supposed to pass through, nibble a lobster roll, tick off a couple of historic sites and move on with my life. But no, Boston, you had other plans.
You didn’t chase me. You didn’t dress up for me. You waltzed in wearing cobblestones and red brick, threw a Fenway Frank at my face and then romanced me with your history and your stories and the kind of sarcasm that cuts just deep enough to leave a mark without drawing blood. You were friendly without being in-your-face. Generous without being showy. Confident without being smug. Smart without being pretentious. Funny in that dry, clever way that makes my brain fizz.
My entire visit felt less like a holiday and more like a blind date with some aloof intellectual —the deliciously brooding kind who smells faintly of old books and Jameson, rocks perpetually rumpled hair, and somehow still looks like he walked straight out of a magazine shoot. The type who acts like he’s above it all but secretly binge-reads Romantic poetry, knows his wine, and then, just when you think he’s too cool to care, says something so utterly charming it completely sweeps you off your feet.
Because sweep me off my feet, you did, Boston. So much so that I appear to have left a chunk of my heart somewhere between Cambridge and Back Bay… probably in some dodgy bar with existentialist doodles on the bathroom wall.
Now I sit, writing this missive clad in an oversized souvenir Harvard T-shirt (pronounced without the r, of course), afflicted by what can only be described as an acute case of city-induced infatuation.
Sure, since our tryst, other cities have tried to win me over with their sensible grid systems and weather that doesn’t demand hourly wardrobe rethinks. But I just keep thinking about you and your green spaces, your bookish corners, your revolutionary past and your streets that follow no earthly logic because some well-meaning Puritan in 1630 decided a cow path and a tree stump made for a perfectly good property line.
You don’t make it easy, Boston. You’re complicated and opinionated, and your personality… well, it’s a cocktail of contemplation, cold shoulder and charm… served with a wink and a side-eye. But once you decide someone’s worth your time, you give them everything… fun, friendship, the best cannoli in America and enough cultural ammunition to make them feel smugly superior at dinner parties.
I’ll be back. Probably sooner than is reasonable or financially responsible. Not just for the food or the art or the Red Sox. Not even for the way your name sounds when the locals say it. Baw-stin… like a sneeze that changed its mind halfway through.
No, I’ll be back because it turns out I rather liked who I was when I was in your company.
Yours,
A Hopelessly Smitten Traveller.
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An award-winning travel writer and photographer, Aleney de Winter was fresh from school when she first set off to explore the far reaches of Australia with a two-man tent and a beaten-up Kingswood for company. Three decades, and two kids later, and she's still on the go, with her itchy-footed offspring in tow. 