Middlebury (1/252)

a Vermont 251 Club post

this picture of a Middlebury house, from Unsplash, fits the mood and aesthetic of the place quite well

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This is an entry in my Vermont 251 Club series. The main post — which lists all 252 places in Vermont — is here. As I visit each one and write about it, the name will become a live link. Going forward, the entries will be for paid subs. This one is open for everyone as a free sample, so to speak.

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Today is Juneteenth — one of those odd holidays that lands when it lands. So I’m off work on a Thursday, which feels almost illegal.

Yesterday, I was desperate to finish something before signing off for the holiday… but I didn’t. My code has a logic error I still haven’t cracked. Sigh.

I’m a morning person, which works great for remote work. My brain’s best hours aren’t spent commuting, and I don’t show up to my desk already sliding out of peak cognitive form. Instead, I get to tackle my most complex problems when I’m mentally sharp — often before 7 a.m.

But coding and math are demanding, and when my brain is done, it’s done. Sometimes around 3:30 p.m., I realize I’ve turned into a zombie.

That was yesterday. And I was frustrated when it hit me that I wasn’t going to finish before the holiday.

Over lunch, I finished writing a post about managing depression that had been sitting in my drafts for a couple of weeks. And I decided to take my own advice: do something fun — something that brings me joy.

Google told me there was an independent, locally owned art supply store in Middlebury that would still be open when I got there.

So I headed out.

A Quintessentially Vermont Drive

The drive to Middlebury was, in a word, Vermont. All two-lane roads, of course — the kind where the speed limit signs are mostly decorative and “passing lane” is a phrase you vaguely remember from a driver’s ed textbook. I spent seven full minutes behind a tractor doing a stately 18 in a 45, a solemn little funeral procession for momentum.

Eventually, the tractor pulled over, and we all surged forward like horses loosed from a paddock.

For once, the weather cooperated. A rare non-rainy day in what’s otherwise been a summer of puddles pretending to be ponds. Umbrellas have gotten more use than grills. Walks have been tentative and upwardly paranoid, as if we all feared Jupiter, God of Weather, might smite us for enjoying the sun.

But this day? Sunlight filtered through the maples like it had just remembered how. The air smelled like wet grass, warming pavement, and distant cow.

Barns dotted the roadside in a kind of architectural bimodal distribution — half looked hand-crafted by Norman Rockwell, and half by his slightly grungier cousin. All had peeling red paint, leaned at charismatic angles, and seemed equally likely to host a wedding photoshoot or actual cows.

The houses ranged from classic white-clapboard saltboxes to what I can only describe as architectural identity crises — like someone tried to build a colonial and a ski lodge at the same time, got halfway through both, and shrugged.

People were out — real people — wearing shorts like a declaration of war against Jupiter and his demigods. Some were gardening. Some lounged on porches, sipping something cold. One guy stood in his yard, arms folded, gazing proudly at absolutely nothing.

It felt like the whole state had decided: we will have summer, even if we have to do it in defiance of the calendar and the clouds.

I also started counting political signs, because I’m me. Eight total. Eight total: four about Black lives and names worth saying, four about God, America, and the importance of pride. But American flags outnumbered everything — by far.

They were everywhere: porches, mailboxes, even one draped vertically on a barn like a Toby Keith fever dream.

Even in towns where you’d expect more cynicism, patriotism was in full bloom. And honestly? It felt kind of great.

By the time I pulled into Middlebury, I was already charmed. Downtown looked like a Hallmark movie set — but with better coffee and fewer fake snowflakes.

Of course, I knew what the picture-postcard charm was glossing over. Middlebury’s the kind of place where unpopular speakers get physically attacked by Middlebury College students — mostly spoiled, Woke kids whose private education runs close to ninety grand a year.

I did a quick self-scan for any visible signs of non-Wokeness and gave thanks I hadn’t worn my AMURICA, FUCK YEAH t-shirt.

Then I stepped out onto an actual sun-warmed sidewalk, which felt like a spiritual experience after the spring we’ve had.

Middlebury, you had me at decent parking and sunshine. Even knowing full well that some of your youth, if granted ten minutes of telepathy, would curb-stomp me, livestream it, and call it community service.

Still, I carried that cautious optimism into my first Vermont 251 Club adventure.

Sparrow Art Supply

Almost everything had closed in the previous hour, but Sparrow Art Supply was still open — a small miracle, really, considering how thoroughly Vermont seems to roll up its sidewalks after 4:00 p.m.

Sparrow was exactly the kind of place that makes you glad you didn't settle for Amazon. Tucked into a tidy space just off the main drag, it had a charming gallery wall showcasing local artists and the sort of curated chaos that tells you a real person is behind the inventory choices.

Most of the stock leaned toward painting supplies, but there was also an unusually high percentage of hands-on creative tools for kids — not just the usual shrink-wrapped markers and sticker kits, but things that encouraged actual imaginative play.

I picked up a reverse coloring book, which is exactly what it sounds like: the pages are already full of watercolor blotches, and you add the lines. Structure imposed on chaos. My kind of metaphor — a mathematician’s dream. Fun and also freeing, since I do it in pen and can neither correct my mistakes nor improve on my first, rough efforts.

I also grabbed a Blackwing pencil sharpener — one of the few types I’d never tried. It’s not ideal for colored pencils (too sharp an angle), but so far it’s doing beautiful work on graphite.

The owner was running the register, and she was everything you hope a small business owner will be. Warm, smart, unpretentious — the kind of entrepreneur who doesn’t just run the store but lives it. We got to talking, and she knew everything. Not just about which pastel brands play nicely together or how the Derwent Lightfasts hold up in sunlight — but also the corporate intrigue behind Faber-Castell’s U.S. distribution politics and the slow decline of Prismacolor’s quality control over the years.

I could have talked to her for an hour. She radiated that rare mix of expertise and joy — the kind of person who reminds you that small business isn't just an economic category; it’s an art form in its own right.

By shopping there, I even fulfilled one of my self-imposed goals for this Vermont 251 Club project: support a local business in each town I visit. I didn’t linger downtown long enough to take pictures — 5:00 traffic makes me nervous, especially as a deaf driver — but I got started.

And that counts.

Next time, I’ll plan ahead. Snap some more photos. Spend more time exploring. But for a spontaneous Thursday in June, it was a pretty great start.

Pictures below.

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