How to Spend a Day in Toronto: Dundas West & Ossington


In our how to spend a day in Toronto series, we share how to make the most of the city’s neighbourhoods and check out places that you wouldn’t find on your typical list of must-see sites. 

Toronto’s west end has established itself as the trendy place to eat, drink, shop, and just exist. Absent are the big retailers and chain restaurants of the core - rather, streets are lined with cool and quirky bars, restaurants, and acclaimed fashion boutiques. 

We’d like to hone in on the ever-so-contemporary Dundas West and Ossington area and the influx of unique places you can spend a day exploring. From morning to night, you can live your most in-the-know life with this How to Spend a Day guide. 

Let’s start with breakfast. Actually, we mean brunch - much cooler. Just a stone’s throw from Trinity Bellwoods Park, you can’t miss the new-to-the-neighbourhood Sisters & Co Restaurant. With upscale menu items such as the Mushroom Truffle Benedict and Earl Grey Pancakes, this eatery founded upon principles of friendship, diversity, and good food is sure to satisfy. And for a dining experience akin to a Paris bistro, we recommend Union for simple, yet hearty fare. Interestingly enough, Coldplay has eaten here which is plenty good reason to see what the hype is about! Late risers will be happy to know brunch is served until 3pm.

It’s now time to hunt for some fresh threads at the same boutiques and vintage shops that dress Toronto’s fashionistas. For the athletic (or athleisure) type of guy, The Local is the Lululemon men’s store that gives off sophisticated bachelor pad vibes. To really sport your love for the 6ix, head over to Peace Collective to pick up the iconic “Toronto Vs. Everybody” graphic tee. This pride runs deeps as Peace Collective is an offshoot of the Peace Foundation with a portion of proceeds from select items going to local Canadian charities. 

If you’re into the thrill-of-the-find, there are some great options for curated vintage shopping along Ossington and Dundas West as well. For the high-end maven, you can peruse designer garments at Rescue Vintage and perhaps give them a new home in your closet. A bit of a different feel is apparent at Penny Arcade Vintage on Dundas West just west of Ossington. From tawdry eighties stuff all the way up to pressed super-rare vintage, there is something for every style at this romantically cozy outfitter.

After a fruitful shopping spree, it’s time to refuel. Why not sit down to a traditional cream tea service at the Kitten and the Bear? A jam-based lunch sounds delightful. Reservations for the weekend can be made online and if you are visiting during the week you can dine in the cafe. You’ll feel like you’re sitting in an English countryside cottage while you sip premium teas and snack on buttermilk scones with unlimited jam. Yes, unlimited!

If jam and scones aren’t your ideal lunch pick, there are plenty of other choices in the neighbourhood for a more conventional afternoon meal. We suggest the all-day wine bar Paris Paris for French-inspired bites paired with a glass of vino. The atmosphere alone is reason enough to visit - with two skylights bringing natural light into the airy 1,500-square foot space adorned with plants and wood finishings, you’ll never want to leave.

A much needed recharge is now in order and what better place to lounge about and people watch (or dog watch) than Trinity Bellwoods Park? Here you’ll find three ball diamonds, eight tennis courts, two volleyball courts, an artificial ice rink, a dog off-leash area, a picnic area, wading pool, and playground. Not to mention slackliners galore. Grab a coffee from Pilot Coffee Roasters before heading over to the park for some R&R. And if lunch is still on your to-do list, you can pick up a pre-made picnic basket from H Bar conveniently located near the south-east corner of the park. Picnic basket options include the Simple Basket for Two at $30 or if you’re feeling a little fancy, opt for the Deluxe Basket for Two for $50. This is the perfect place to kick back, snack, and take in the scenery before getting ready for the fun-filled evening ahead.

Time for dinner already? Okay! This time, jaunt back over to Ossington for some Korean-American fusion at the hidden gem that is Oddseoul. Might we suggest starting with the Buffalo Fried Tofu? You won’t believe it’s not wings! For your main, the Sizzling Brick Chicken plate can easily be shared between 2-3 people and be sure to ask for more radish wraps if you need them!

It’s the moment we’ve all been waiting for: dessert! Just across the street, you might see a line forming down the sidewalk for the tried and true Bang Bang Icecream. With unique and questionable flavours such as Corn on the Cone and Double Smoked Bourbon Bacon, this place is a must-try, especially if you opt for an icecream sandwich with your choice of cookies. Bon appetit!

Bang Bang Icecream

Bang Bang Icecream

Dundas West and Ossington is well known for their bar crawl scene and we have a few recommendations for spots you can add to your list. 

The ever-so-popular Bellwoods Brewery is a great place to start your safari with the sour and hoppy Jelly King beer. Next, you can make the quick walk north to Communist’s Daughter, an artistic and homey hideaway that features live music on weekends. Going west on Dundas, pop into Get Well for a pint and game of pinball and then over to the local’s favourite hole-in-the-wall, E.L. Ruddy. The Dakota Tavern is another must-visit for live music with Neil Young once gracing the stage. If you’re into the hip-hop scene, there is no better bar than Red Light (especially if you’re ready for the dancefloor). Cap off your crawl with the bar that nearly broke the internet. Yes we’re talking about The Lockhart, a Harry Potter-themed bar at the corner of Dundas and Dufferin. Indulge in some magical potions and elixirs for an experience beyond mortal scale, or if that’s not your thing, there’s always craft beer on tap.

For a take-away eats you can end your night at Bobbie Sue’s, Toronto’s first all mac-and-cheese eatery. Located in a colourful shack, the to-go service concept operates solely as a walk-up window. As the cooler weather sets in, this cheesy comfort food serves as a great alternative to the popular post-bar poutine.

Make your visit to Toronto worthwhile and explore the city’s most happening neighborhoods with us on a guided tour! Make friends from near and far on a group tour or work with our travel planners to craft a customized private journey. Our expert Torontonian guides will take you beyond the obvious tourist spots to see Toronto’s charming personality.