I planned the ultimate date night in Toronto then just brought my dog instead

The Distillery District has all the ingredients for the perfect summer date night in Toronto: historic brick laneways, beautiful patios, festivals, great food, cocktails and an atmosphere that begs you to slow down and stay awhile. 

But who says you actually need a date? Or, more specifically, a human one?

As a dog owner, my favourite summer evenings in Toronto are usually spent with my four-year-old cockapoo, Lainey. She's my adventure buddy, my excuse to explore another neighbourhood and, judging by the number of strangers who stop to say hello every time we go out, easily the more popular half of our duo — which I'm perfectly okay with.

The Distillery Historic District.

So instead of waiting for someone to ask me out, I planned what I thought would be the ultimate summer date night in the Distillery District with the one companion who's always happy to come along.

Dinner and a movie might be the classic date-night formula, but thanks to the Lavazza IncluCity Festival, the Distillery District puts a one-of-a-kind spin on it every summer. The annual outdoor film festival transforms the neighbourhood into an open-air cinema village, complete with tasting stations, live activations and nightly screenings beneath the stars.

It had been sitting on my Toronto summer bucket list for weeks, so I planned our evening around it: dinner on Cluny Bistro's dog-friendly patio, followed by a movie at the festival, which I was delighted to discover welcomes dogs, too.

Sniffany & Co.

The moment we stepped into the Distillery District, Lainey confidently led me straight to Sniffany & Co. We've visited enough times that she seems to know exactly where it is, and I laughed as she practically dragged me through the front door.

It's one of my favourite shops in the Distillery, too. Inspired by Tiffany & Co., the boutique is decorated in the brand's signature robin's-egg blue and is filled with clever dog toys and accessories that always make me giggle. Before we left, the staff handed her a complimentary treat from behind the counter, which she accepted like a regular customer.

We then made our way to Cluny for our dinner reservation, and while it was only a short walk, Lainey turned it into a much longer one. 

We're used to this.

Every few steps, someone politely stopped to ask if they could say hello. She greeted passing dogs while I chatted with their owners about her breed, her age and, inevitably, how cute she was. As long as people ask first, those little interactions are one of my favourite parts of having a dog in Toronto.

It's funny how bringing my dog changes the feeling of going out "alone." By the time we reached Cluny Bistro, we'd already struck up conversations with so many people, met a handful of dogs and shared more smiles than I probably would have on most dinner dates. I certainly didn't feel like I was dining alone.

Cluny Bistro.

The staff greeted both of us just as warmly, welcoming Lainey with the same enthusiasm they had shown me before, then quickly returned with a fresh bowl of water for her. As a dog owner, little touches like that never go unnoticed.

Our table was tucked into Cluny's lush courtyard patio, where climbing ivy, twinkling fairy lights and shaded corners make it feel as though you've stumbled into the French countryside. Lainey curled up beside my chair while the buzz of the Distillery District faded into the background.

My meal was just as memorable. I had their new summer chèvre, a creamy goat cheese brûlée served with compressed watermelon, New Farm arugula, Anaheim chili and basil, followed by the handmade ramp tagliatelle with Toulouse sausage, spring greens, Parmesan and aglio e olio. 

Sitting on one of Toronto's prettiest patios with a summer cocktail in hand and a happy cockapoo snoozing under the table, it was all absolutely lovely.

Cluny Bistro.

Instead of instinctively reaching for my phone between courses, I found myself scratching behind Lainey's ears and smiling back at fellow guests who stopped to admire her. Some asked if they could say hello. Others smiled as they walked past or laughed as she made eye contact with them from beneath my table.

As we were getting ready to leave, the staff surprised Lainey with a dog cookie. By the look on her face, she's decided Cluny is absolutely worth returning to. 

Cluny Bistro.

One of the things I love most about the Distillery District is that it's designed for wandering, so having the Lavazza IncluCity Festival woven throughout its streets felt like a natural extension of the evening rather than a separate event.

Every festival ticket includes access to a tasting experience, with food and drink stations scattered throughout the village alongside art installations and interactive activations before the nightly outdoor film.

One minute I was sipping an iced Lavazza cold brew that ended up being exactly the boost I needed to stay awake for a late-night movie, and the next I was sampling bites from Barilla, Eataly, Ferrero and Rio Mare before picking up a glass of Masi Prosecco to enjoy as we wandered. By the end of the night, my tote bag was filled with little souvenirs from the festival, including Kinder eggs, Tic Tacs and enough boxes of Barilla pasta to make several dinners at home.

Around us, people lined up beneath the giant G Adventures hot air balloon for photos, ducked into the AiRTIFICIAL Visions exhibition, posed in the Lavazza photo booth and lingered wherever music happened to be playing.

Of course, Lainey wasn't about to let me have all the treats.

Scooped by Demetres (Distillery District).

We made one final stop at Scooped, where she was handed a pup cup that was considerably larger than either of us expected (I didn't let her finish it, poor thing.) While she happily worked her way through that, I enjoyed a cup of their Dubai chocolate flavour. I'm still not over the Dubai chocolate obsession, and I hope that trend sticks around for a while.

As the sky began to darken, people slowly started making their way toward the festival's outdoor theatres.

ICFF.

I picked up my wireless headphones and found one of the oversized inflatable couches waiting beneath the screen. This might be one of the most dog-friendly movie experiences I've come across. Instead of projecting the sound through loud outdoor speakers, everyone listens through headphones, so the atmosphere stays remarkably calm for four-legged guests while still feeling completely immersive for everyone else.

That night's film was Five Seconds (2025), an Italian drama. I don't mind subtitles in the slightest, and within a few minutes I'd completely forgotten I was reading them. Beside me, Lainey curled into a little ball on the couch, occasionally glancing up as people settled into their seats before drifting off to sleep.

I couldn't think of a better way to end a Toronto summer evening.

A summer night well spent.

The Lavazza IncluCity Festival runs until July 19, so there's still time to experience one of Toronto's most unique summer date nights. And if your favourite plus-one happens to have four legs, the Distillery District might just be one of the best places in the city to spend a summer evening together.

Lainey went home with a complimentary cookie, a giant pup cup and several new admirers.

I went home, reminded that the best date nights aren't always the romantic ones. Sometimes they're the ones where you laugh with strangers, discover new places and spend time with your fur baby by your side.