Disclaimer: This will vary from person to person.
For example, I will simply never understand those who yearn for small-town life — but they are in fact out there. I can imagine living in a suburb (within proximity to the city), but the Torontonians I've met who fantasize about moving as far north of the city as possible to surround themselves with the slow, stillness of the countryside? Permanently?
We are not the same.
But, in the name of public service and at the cost of exposing my classic Torontonian snobbery, I ranked a handful of Ontario cities based on how long I'd realistically think I could survive living there — my idea of the best and worst.
#1 — Vaughan
I really tried to be unbiased here, I really did.
I grew up here. I know it inside out, and if anyone has a reason to hate Vaughan, it would be a girl who was unwillingly stuck there her whole upbringing. However, if we look at it unbiased, it has everything you actually need to sustain long-term living, especially if you're tied to city life.
First of all, close access to the city. The subway connects to Vaughan directly. Some would even argue (not me, absolutely no true Torontonians come for me when I say this) that Vaughan is basically an extension of Toronto. More often than not, if you're out in the city and you ask a Vaughan girl where she's from, she'll probably say Toronto.
Next order of business, and arguably the most important for me: the food (sue me, I'm a food writer). If you know absolutely nothing about Vaughan, you really only need to know one thing: it's predominantly Italian-Canadians. Think: the cast of Jersey Shore. And if you know nothing about Italians, you really only need to know two things: Italians know how to eat, and therefore how to cook. Sorry, but ask anyone who's moved out of Vaughan — no one else in Ontario knows how to make bread like them. The bakeries, the restaurants, the cafes... all unmatched.
As for sites to see, Wonderland is a place for both tourists and locals alike, and it never gets old. Take it from someone who had a season's pass ages 10-17. This is the place most kids/teens only dream about spending their summer.
Yes, plazas on a summer night are filled with people smoking cigarettes. Yes, we all hate Vaughan Mills. But culturally? Socially? Logistically? It just works.
Verdict: Decades (against my better judgment)
#2 — Oakville
Okay, yes, Oakville technically is a town, not a city — but it is a decent size.
It's also beautiful in a way that feels cinematic. The kind of neighbourhood that feels like the Cheaper by the Dozen house fits right in. Or the kind of driveway where you'd see Steve Martin and his daughter having a basketball game followed by a heart-to-heart in Father of the Bride.
Between the lakeshore, the tree-lined streets, and the neighbourhood scenery – it's all there. The downtown strip is what the Kleinburg strip (in Vaughan) wishes it were. It also has incredible access to the train and gets you downtown within a half hour, which, as we've already established, is essential for me.
However, and I need to say this in the name of honest, boots-on-the-ground journalism — the food scene just doesn't hit the same. Yeah, they have Piano Piano – but anything else? And yes, I'm using bread as my benchmark, and I'll stand by that.
Oakville is close to perfect, but I'd eventually get bored.
Verdict: 5-8 years (before settling somewhere I can get a real salami sandwich)
#3 — Hamilton
Hamilton is in its glow-up era.
What used to be primarily known for its industrial roots has very quickly grown into a hub of culture, arts, and once again (the most important aspect), a foodie city. The restaurant scene is growing fast, with bars and restaurants that could rival Toronto. With the recent renovations to the TD Coliseum, who needs GO trains when concerts can happen in your own backyard?
Plus, the proximity to nature makes one hell of a case for moving. Waterfalls, hiking, views – it's everything a nature-junkie needs.
Distance-wise, there isn't a huge difference between Vaughan, Oakville, and Hamilton. The only con that comes up for me is the rising homeless population in Hamilton. One of the visible growing pains that the city's yet to address as it continues to evolve.
Still, I could see myself doing a chapter here.
Verdict: A few years (in a "cool, slightly removed from Toronto" sort of way)
#4 — Guelph
Guelph is a town that exists in a very specific phase of life. The earthy, crunchy, granola phase.
The major attraction here is the University, and more specifically, the arboretum that comes with it. Tons of green space associated with the university campus that serves as a living laboratory for teaching and research. Featuring extensive walking trails, botanical gardens, and specialized plant collections to conserve biodiversity.
In saying this, the food scene has a strong farm-to-table presence, which is always a win.
The party scene is decent, though mostly for the ultra-young university crowd. There's access to some incredible thrifting and honestly, the main street makes a case for appeal — for a minute.
Guelph is a casual fling, a summer romance until you come to your senses. Long-term? Incompatible.
The food scene is fine, not life-changing. There's no major mall, no real "big city" pull. It's charming, but limited. I could spend a summer here. Maybe even a soft cottagecore era.
But beyond that, I’d miss the chaos of the city.
Verdict: 2-3 months (no situationship should last more than this)
#5 — London
Up until now, I've had something nice to say about every town. Here's where we see the shift. I've been to London, Ontario, twice in my life. Both were against my will.
It's far. Like commitment-level far. And to drive all that way to be underwhelmed? Another University town, but outside of that, the city feels like it's missing something – or several things.
The nightlife is aggressively student-focused, the infrastructure feels dated, and getting there without a car is an experience I wouldn't recommend to my worst enemy.
They have parks, sure, and a drive-in movie theatre. But none of it feels like enough to justify staying.
Verdict: 36 hours at max (only because it's so far from Toronto, I need to stay overnight)
#6 — Waterloo
Yes, I hate university towns. I hated university towns when I was in university. Why is everything sticky? And why is everywhere loud?
With two universities side by side, Waterloo feels like a place where the only big player is a university. Everything revolves around it. The nightlife, the student-focused rental buildings, and the general state of chaos that runs through the streets anytime after midnight. And if you happen to land there on homecoming weekend (which I unfortunately did), it's game over.
Last time I went to Waterloo, I woke my friends up at 5 a.m. to catch the 6 a.m. first bus of the morning before the sun even rose.
Verdict: 12 hours (and that's generous)
I really would like to believe that I could thrive anywhere. But we all must unapologetically accept who we are. In reality, I'm needy. I have high expectations. I'm high maintenance, and I'm proud.
Some cities are for living. Some are for visiting. And some are meant to be left before sunrise. Use this information wisely.
This article has been updated from its original publication date.
The opinions expressed in this article are the author's own and do not necessarily reflect the views of Narcity Media.
