The James

James Street in Hamilton tells the city’s story through every block, every shopfront, every gathering that spills into the street. It has two distinct ends: the north, which historically belonged to Italian and Portuguese communities, and the south, where the city’s hospitals sit and where larger houses reveal the old geography of class. For decades, the steel mills shaped everything here. Management families lived further south, away from the smoke, while workers stayed closer to the industry. That stratification is still visible in the houses today.

The real cultural heartbeat of James is its north end. This is where the Art Crawl began in 2007, a monthly ritual where galleries opened late, shops welcomed visitors, and people lingered on sidewalks with wine in hand. It was a spark that transformed the neighbourhood overnight, pulling energy and attention into Hamilton’s downtown. Out of it grew Supercrawl, a massive annual festival each September that shuts the street down entirely and fills it with tens of thousands of people, live music, murals, installations, food stalls, and community. For one weekend, James becomes a pedestrian commons, alive with every layer of Hamilton’s cultural life.

James is defined by contrast and coexistence. You’ll see old Italian and Portuguese social clubs tucked between cafés and new restaurants, Jewish clothing stores holding ground beside barber-bars and design shops. Collective Arts Brewery, born in Hamilton and now nationally known, still carries its roots here by commissioning artists for every can. That mix of immigrant history, creative experimentation, and entrepreneurial spirit gives the street a texture unlike anywhere else in the city.

People often compare James to Ossington in Toronto, and the comparison makes sense. Both strips carry that sense of discovery: art galleries next to bars, a little grit alongside ambition. But James hasn’t been entirely priced out yet. It’s still grounded. Families who’ve been here for generations walk the same sidewalks as newcomers setting up studios, shops, and restaurants. That coexistence is delicate. Like Ossington, James faces gentrification pressures as Toronto’s rising costs send people west. But James still belongs to Hamiltonians first, and that’s what keeps it alive. A street can’t sustain itself on day-trippers; it needs the people who walk it every day.

Walking James is to watch Hamilton negotiating its past and its future in real time. The immigrant-founded businesses are still here, though some close under redevelopment. New creative ventures open in their place, while long-running institutions hold the history. And the street itself has been marked by decades of city planning decisions, some disastrous — like one-way traffic corridors and mid-century malls — that disrupted the fabric. Today, movements are underway to bring two-way streets back, to make the downtown more walkable, to let people stop instead of just driving through.

James Street is more than just a commercial strip. It is Hamilton’s cultural artery, carrying the city’s identity and aspirations block by block. It thrives not because of big institutions but because people keep showing up — to crawl, to celebrate, to shop, to live. It’s not polished, but it’s alive. And that, more than anything, is what makes it vital. ─Ryan Moran 

The Ossington

“Meet me on Ossington” ─ that’s the slogan that rallies the smattering of shops, cafés, and restaurants lining the commercial stretch between Dundas St. and Queen St. What was once a modest strip of mechanics, Portuguese bakeries, and unassuming storefronts has, over the past two decades, transformed into one of Toronto’s most dynamic cultural corridors. In my earliest memory of Ossington, I’m running towards Bellwoods Brewery circa fall 2014, after my date had left her phone on their patio. The phone was still there when I arrived, and Bellwoods too is still there 12 years after first opening its doors. In fact, Bellwoods has grown, taking over property next door — a home decor shop I used to work at — and its Jelly King sour ales have become a Toronto staple.

On any given Sunday, weather permitting, the strip is buzzing with an assortment of artists, students, retirees, young parents, academics posing as socialites, fellow broke millennials YOLO-spending, nepo babies posing as penny-pinchers, and influencers posing next to everybody else. It’s the place to be, if you can afford it. 

The past decade has been one of relentless gentrification, and my gripes are born of watching the more modest businesses and residents get routinely priced out of Ossington as landlords and other culture-vultures cash in on the cool they didn’t contribute to. Yet, there are rarely any villains here: for, at bottom, everyone is struggling against the social inertia that keeps consumers at home and online. In that sense, Ossington is a bit of a miracle, a rare shining example that the brick-and-mortar model still works for retail and service industries in Toronto. It’s the result of small businesses (and sneaky corporate conglomerates) giving the good ol’ college try in the belief that a street isn’t just a collection of buildings. That you really can build a place to be out of thin air (and thick wallets); and, with enough municipal buy-in, you have something verging on a real cultural destination—a place that you can connect to emotionally, a place built to last.

In the early 2000s, Ossington was far from the glamorous hyped-hub that it is now. Auto body shops dominated alongside cheap rentals and family-run businesses serving the area’s large Portuguese community. The strip’s affordability and vacancy, however, also made it fertile ground for artists and entrepreneurs originally priced out of Queen West. Bellwoods is the rare example of a business that first benefited from this vacancy and is still whinnying with us today. The Portuguese bakery at Ossington and Argyle Street gave up the ghost during the pandemic; not even the corporate funding behind the eyewear store I used to work at could keep up with the rent; and Superpoint Pizza — the best pizza in the city, I’ll die on this hill — couldn’t survive 2025. Life in the big city.

Nevertheless, something truly special persists in the oeuvre of this strip. It’s hard to pinpoint what makes Ozzy special, except that there’s nowhere else like it in Toronto. Last year, after a dearth of not getting even a single interview, I suddenly found myself with three offers from medical schools across the province. Two of these schools could make a good case for leaving Toronto for good, one program even promised to turn you into a doctor in three years instead of four. So I found myself in a real conundrum about what makes the headaches of Toronto worthwhile, and why so many young professionals have been exiting the city since the pandemic. Walking down the strip one Sunday, in the middle of this deliberation, the choice suddenly became clear, and I resolved to the conviction that I should avoid anything that could take me away from my Ossington heart.

I’ve got The Ossington on my wrist as I write this at I Deal Coffee & Wine—another spot that’s been on the strip since forever. It’s a beautiful Sunday. Locke & King’s dual mottos — “Upward and Onward” and “Make Your Own Time” ─ feel especially relevant to this time and place. Toronto’s hustle culture is truly breakneck stuff, the constant hurry, the relentless reinvention. It’s easy to forget that the things that make the upward climb worthwhile are not found at the top of wherever it is you’re trying to get to. You really do have to make your own time for the things that matter. You have to find something genuine and real amidst the gentrified layers of wherever it is you’re reading this. —Michael Zarathus-Cook