How to spend a perfect day on Toronto’s Ossington Avenue

Whether you’re new to Toronto or you’ve been here a long time, a day on Ossington is always in the cards. While the street is mostly residential between Davenport and College, the strip between Dundas and Queen is a hot spot for restaurants, bars, and shopping.

The thing is, there’s so much to do, it can be tricky to narrow down the options. Have no fear, though. As a lover of all things Ossington, I’ve been around the block a few times. Literally.

Here’s how to spend the perfect day on Ossington.

The morning

For this perfect day, you’re going to arrive at the strip at around 11:30 a.m. This is the ideal time for activity number one: a stroll to get coffee and a treat.

The coffee and the treat will be from separate places, but caffeine comes first. Nestled right by the intersection of Ossington and Argyle is Sam James Coffee, and while I’m not a coffee snob, some of my friends are, and they love it here. Not only is the coffee great, but the employees are sweet as pie.

Next stop, Andreas Cookies. You’ll want to get here before noon, as they open at 11 a.m. and there will likely be a line. This locally owned spot has the best cookies ever, and if the strawberry milkshake one is in stock, grab it. And a cinnamon bun cookie, too, if they have it.

The afternoon

It’s around 12:30 p.m. now, and it’s time for a little fun.

While this place is off Ossington, it’s only about a one-minute walk off the main strip. Penny’s Arcade is an amazing vintage shop that offers more than just one-of-a-kind finds. The store also has a vintage photo booth, and for less than $10, you can get some beautiful photo strips to keep forever.

The shopping continues back on Ossington at I Miss You Vintage, for more vintage (designer) finds, and The Latest Scoop, a trendy clothing and accessory store that has helped outfit me for nights and days out since 2022.

Now, it’s beer slushy o’clock. You heard that right.

Bellwoods Brewery sells its signature beer, the Jelly King, in slushy form. It’s truly life-changing. Grab one and relax on the patio, or stroll down the road to enjoy it at Trinity Bellwoods Park.

Getting hungry? While there are constant debates on what the best slice of pizza in the city is, I really love Superpoint. I crave the pizza very often, and it doesn’t hurt that the cocktail and wine list slaps.

The evening

Alright, we’ve made it to the evening and drinks (mocktails or cocktails, I don’t judge) are in order.

Two options for a pre-dinner cocktail or mocktail: Bar Banane or Bar Bowie. Both will likely require a reservation, especially if you’re going on the weekend. Bar Banane has a very cool interior, and a list of drinks that I couldn’t think up on my own if I tried. It’s also a perfect place for that “pre-dinner” Instagram story.

Bar Bowie is equally as cool, tucked behind a laundromat. This (literally) underground spot has one of the best dirty martinis I have ever had, so if that’s your jam, head on over.

My favourite time has arrived: dinner time.

Okay, so the options are kinda endless, and while most people will recommend somewhere like Mamakas (literally so good), I’m going to offer up a couple of other places.

Criminally underrated is Foxley, where Pan-Asian food is done so insanely right. From pan-fried lamb and duck prosciutto dumplings to marinated beef short ribs to steamed whitefish with asian greens and truffle sauce, it’s all incredible.

Recently, I tried The Lunch Lady, and guys. It is one of my new favourite restaurants. Known for their twist on Vietnamese street food, the dishes here are out of this world. One of my favourites was the Mi Xao Toi with egg noodles, XO garlic butter, parmigiano, slow-poached egg, and red crab. Yum.

Another awesome option is Linny’s, a somewhat new steakhouse with a bit of a fancier vibe, so if that’s the feel you’re going for, make that reservation.

Alright, folks. The day has come to an end. Ossington is truly one of the greatest places, and I hope my itinerary comes in handy!

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