Extreme Layover: Calgary, Alberta, Canada

To The Extreme
It’s been a minute since I pulled off what I like to call an “Extreme Layover.” For the uninitiated, that’s when the universe hands you a layover long enough to do something stupid, brilliant, or both—like running headfirst into a city with barely enough time to taste its grit and maybe get lost on purpose. This time, it was Calgary. Nearly 24 hours. Just enough time to get into a little trouble.

Now, yeah—flying from San Diego to Calgary en route to Tokyo doesn’t exactly make sense on paper. But travel, like life, isn’t always about straight lines. It was the cheapest route, sure. But I saw an opportunity to get a taste of Alberta, and I took it. Calgary: oil money, cowboy boots, snowy peaks in the distance, and a skyline that’s somehow both futuristic and grounded in the dirt.

This was Canada visit number five for me, but Alberta? That was uncharted territory. And that gets my blood going. A new city, a new story. No expectations. Just curiosity, cold air, and whatever was cooking downtown. I was ready.

There’s something quietly thrilling about trying a new airline—especially when it doesn’t suck. WestJet, in this case. Not bad. I managed to swing a decent fare in business, which meant a few hours of cushy, uneventful cruising from San Diego to Calgary before the long haul to Japan. No drama, no screaming babies. Just altitude and anticipation. By 5PM, I was on the ground. By six, I was tossing my bag onto the hotel bed. By 6:30, boots on pavement, heading out into the cold Canadian evening in search of something edible, something real.

The walk took me out of downtown, across the Bow River and through Prince Island—snow still clinging to the ground like a leftover thought. It was peaceful, quiet in that distinctly Canadian way. Along the path, I saw it: this absurdly large, impossibly white rabbit. Like something conjured from a Scandinavian children’s book—beautiful, serene, maybe slightly demonic. Wild? A runaway? No idea. But it stopped me cold. Calgary was already full of surprises.

RAMBLIN’ TIP: Find a great hotel in Calgary HERE.

Then came the stairs. Wooden, steep, and seemingly designed to punish the unprepared. I climbed, lungs burning, rewarded with sweeping views of that clean, photogenic skyline. I kept going, eventually threading through a quiet neighborhood—the kind of place where people barbecue in hoodies and kids leave bikes on the lawn. I like seeing where people live. Not the postcard version of a city, but the real thing. That’s where the stories are.

Dinner Plans
Dinner was at a place called Sallora—no white tablecloths, no pretense, just a counter, a steam table, and the unmistakable smell of garlic, cumin, and something slow-cooked and honest. Middle Eastern joint. The kind of place where the food does all the talking, and thank God for that.

I ordered the veggie plate: rice, roasted potatoes, fattoush salad, falafel, dolma. A heavy tray of comfort and spice for about 14 bucks. And let me tell you—this was good. Like, dangerously good. The kind of good that makes you wish this was in your own neighborhood so you could abuse the privilege three times a week until your pants stopped fitting.

Against my better judgment—and any sense of self-control—I went back for round two. Chicken and rice, plus a massive round of flatbread the size of a car tire. No regrets. The guy behind the counter, Syrian, had that easy smile of someone who’s survived things you can’t imagine and still manages to care how your plate looks.

I left painfully full, slightly ashamed, but also happy. The kind of full that makes you walk a little slower, breathe a little heavier. Luckily, I had a mile and a half ahead of me to digest it all—food, experience, and that quiet Canadian night.

Snooze Button
I probably slept in a little longer than I should have. Rookie move, sure—but sometimes a warm bed in a cold city wins the battle. Time was short, but I made the most of what I had. Priority one: pastries. Always.

I ended up at a place called Yann Haute Patisserie—bright yellow house, French as hell, and dangerously inviting. I wasn’t expecting much beyond the usual morning sugar bomb, but then I bit into what can only be described as pastry perfection: an apricot-passion fruit kouign-amann. Sticky, buttery, flaky—this thing didn’t just sing, it screamed. Straight onto the Ramblin’ Randy “Best-Of” list, no hesitation. That kind of pastry changes you.

The only downside? No coffee. Not even a sad drip machine hiding behind the counter. So I made the short pilgrimage to Purple Perk, a cozy local spot slinging lattes and good vibes. While waiting for my caffeine fix, I spotted a lonely little tart near the register. It looked at me. I looked at it. Resistance was futile.

“What kind of fruit is that?” I asked, pointing.

“Saskatoon,” the cashier replied, like I’d just asked what planet I was on.

Saskatoon? No clue. Some regional berry that clearly missed the export memo. But damn, it was good—subtle, not cloying, just the right amount of sweet. A quiet little revelation surrounded in a tart shell. Calgary, you weird and wonderful breakfast date—you are starting to win me over.

Booking It
Stuffed with sugar and butter and whatever the hell a Saskatoon is, I made my way to the Calgary Central Library. Now, look—I’ve been to a lot of libraries. Most smell like carpet glue and disappointment. But this? This place is a temple.

It’s a swirling, sensual mass of Scandinavian-feeling wood and glass—like if a spaceship and a sauna had a baby and filled it with books. The curves, the ramps, the endless, flowing ribbons of warm yellow wood wrapping themselves around staircases and ledges… it’s obscene, honestly. Sexy, even. Yes, I said it. This library is sexy. You don’t expect to feel things in a library, but there I was—floored. I could’ve spent a week here, wandering between the shelves and admiring the lines like they were fine art. But I had a flight to catch, and time, like always, was out for blood.

Walking back to the hotel, I soaked up the last of the city—its absurdly clean streets, its skyline built like it actually gave a damn about looking good, and a weird sense of calm that blanketed everything. Not once—not once—did I hear a car horn. In a city. That alone should earn Calgary some sort of medal. It’s a place that knows how to breathe. And maybe, just maybe, it taught me to do the same—for a moment.

The TELUS Sky in Calgary is the city’s third tallest building and named after “Telus Communications,” a Canadian telecommunications company:

Oh, and lots of these indoor “Skywalks…”

…86 bridges and over 16 kilometres of elevated, weather-protected and climate controlled walkways throughout downtown Calgary.

Back 2 the Hotel
Back at the hotel, collecting my things before the 12:30 cab, I couldn’t help but stew in that familiar traveler’s regret—the kind that creeps in when you know you could have done more. Should’ve dragged myself out of bed earlier. Should’ve squeezed in Studio Bell. Should’ve gone up the Calgary Tower, done the tourist thing, stared out over it all from a thousand feet in the air like a proper wide-eyed idiot. But I didn’t. And that stings a little.

Still, this “Extreme Layover” in Calgary? It was a win. A solid, unexpected punch of architecture, flavor, and quiet civility wrapped in snow and skyline. I’d come back—no question. Next time for a proper stay. Two days minimum. Maybe rent a car. Maybe drive up to Banff and lose myself in those postcard mountains people won’t shut up about.

There’s always more to see, more to eat, more to feel. That’s the deal we make when we travel. You never really finish a place—you just run out of time.

See more Extreme Layovers HERE.