The Hippest Streets in Toronto

9 streets you've got to check out

Toronto is full of unique businesses, local boutiques, tasty restaurants, out-of-the-box bars, and so much more.

There are certain streets that tend to boast some of the most distinctive character, the most unique art, and the most creative businesses that this city has to offer. Check out this list of some of the hippest streets in Toronto below.

Augusta Avenue

Augusta Avenue is the main strip of Toronto’s bohemian neighbourhood, Kensington Market. The Augusta strip is full of indie shops, vintage clothes, and art spaces. There’s also tons of Instagram-worthy graffiti and art installations like a car that is filled with a garden. Some of Toronto’s best eats can be found along Augusta from the tasty vegetarian treats at Wanda’s Pie in the Sky to yummy Chilean dishes at Jumbo Empanadas.

Bloor Street West

Bloor Street West boasts some of Toronto’s best eats, clothes, and bars from Christie Pitts to The Annex. Bloor runs through old Mirvish Village, which has always been known for its creativity and public art. If you tour the street as far as Yorkville, you’ll even hit one of Toronto’s tourist artistic spots, the Royal Ontario Museum.

Carlaw Avenue

Carlaw Avenue is a pretty condo-heavy area, but tons of colourful stores from niche furniture stores to homey cafes still trickle throughout this hip street on Toronto’s East end. A lot of the up and coming stores that have set up shop along Carlaw actually have converted old warehouse spaces into chic, modern storefronts.

College Street

The main strip of college is home to Little Italy and is filled to the brim with hip bars, tasty restaurants, and family-run businesses. If you’re looking for some tasty Italian eats this is the place to go. From cheesy slices at Bitondo’s to the classic patio at Cafe Diplomatico, you can find a great restaurant every couple of feet on College.

Dundas Street West

Dundas Street West is a local hot spot for vintage clothes, fashion, and a hip nightlife scene. Little Portugal also boasts some of Toronto’s best spots for seeing art, or creating your own in a studio. Steambox Dumplings recently opened up along the Dundas West strip, which is supposed to be Toronto’s best new handmade dumplings with vegan and gluten-free options as well.

Gerrard Street East

Head to Gerrard Street East if you want to walk through the streets and see stretches of businesses painted in pastel rainbows, or enjoy a meal and a beverage at any of the hip bars like Poor Romeo, Pinkerton’s Snack Bar, Chula Taberna Mexicana, or Farside. Although this street may not be the most famous on the list, it’s quickly becoming one of the most exciting, especially for food lovers. From Kid Chocolate to Mi Mi Restaurant, there’s more good eats than you could ever fit in your stomach along Gerrard!

Ossington Avenue

Ossington Avenue is getting trendier and trendier every day from the Trinity-Bellwoods neighbourhood up to Bloorcourt Village. With acclaimed fashion boutiques like Jonathan + Olivia and the best Korean fusion food you’ll ever have at Odd Seoul, you’ll never run out of things to do on Ossington.

Queen Street West

West Queen West was named with second-coolest district in the world in 2014, with boutique hotels like the Drake and the Gladstone, stylish local clothing stores like Frances Watson, and renowned venues like the Cameron House and the Horseshoe Tavern. Queen Street West is the place to go for tourists and locals alike, whether it’s day or night this is one Toronto street you won’t want to skip.

Roncesvalles Avenue

The homey, family loving community of Roncesvalles is known for its beautiful characteristic homes, cute cafes, and tasty Polish restaurants. Lovingly known to its habitants as “Roncy,” this street has a small town European charm with many family-owned shops and intoxicatingly delicious smelling bakeries.

Lead Photo Copyright Queen’s Printer for Ontario, photo source: Ontario Growth Secretariat, Ministry of Municipal Affairs