Your Little Italy, Toronto Guide: Cafés & Culture in Downtown Toronto

Little Italy offers a heady mix of history and contemporary culture. With its cool restaurants and nightlife—plus live music and Italian festivals—it demands more than one visit. Here are the best things to do in Little Italy, Toronto.

Discover Toronto’s vibrant and diverse Little Italy. While the main drag runs east-west along bustling College Street, the community also includes stretches of Dundas Street West between Bathurst Street and Ossington Avenue. This charming district boasts a rich history dating back to the 1920s and is easily accessible via car, bus, streetcar or subway.

Discover the quieter side of Toronto’s Little Italy by walking side streets lined with Victorian-era houses before sitting on a lively patio with a cortado or Negroni. Food is a major draw here, with some of the best Italian restaurants in Toronto, as well as tasty vendor offerings during its annual street festivals.

Top things to do in Little Italy, Toronto

College Street, Toronto’s nightlife is a strong draw. Hail Mary is a speakeasy that draws a youthful crowd with its DJ, drink deals, neon-lit glow, plus an inclusive no cover charge/no guest list policy. (There’s also a photo booth, so you can commemorate your night out.)

More College Street nightlife worth a peep: Track & Field (located on street level beneath Hail Mary), where you can play bocce, tabletop shuffleboard or hit the dance floor; and El Convento Rico, a College Street institution. The Latin 2SLGBTQ+ focused nightclub is locally loved for its drag shows, dancing and ladies’ nights.

Or catch a comedy show at the Royal Theatre, a former rep cinema that has found new life hosting standup performances and candlelight concerts (classical live music concerts that take place in the glow of thousands of LED candles).

For a quiet moment, stroll over to the Church of St. Mary Magdalene, a peaceful sanctuary that serves as the perfect spot for a moment of tranquillity and contemplation. Continuing down the sidewalk, you’ll come across the Italian Walk of Fame, where stars on the pavement pay homage to prominent Italian figures.

Little Italy, Toronto cafés and restaurants

Trattoria Taverniti will transport you to Nona’s kitchen. Begin your dining adventure with antipasto before indulging in a plate of house-made pasta.

Contrada is an intimate date-night spot offering shareable fare like hamachi crudo, burrata toast and elevated mains like crab-and-roe-stuffed anolini, or halibut alla vignarola with sorrel, fava beans, asparagus and mustard greens.

Another must-visit is Bar Raval, a tapas bar with a wild Gaudi-esque aesthetic. Sip craft cocktails as you nosh on meat and seafood dishes, setting the stage for a delightful night of good food and conversation.

Pro tip: if you’re looking for one of the best gelato spots in Little Italy, Toronto, make a stop at Sicilian Sidewalk Café, the city’s oldest authentic gelato shop. Other cafés worth a visit include Café Diplomatico (which revolutionized outdoor dining in Toronto when it opened in 1968) and Snakes & Lattes board game café.

Support local: Little Italy, Toronto shopping

Karyn Ruiz of Lilliput Hats is one of Canada’s finest milliners. Most famously, Ruiz’s intricate feather-trimmed designs were worn by Gord Downie during The Tragically Hip’s final tour. Drop by her atelier to find your own handmade Panama, beret or fascinator.

Neurotica Records brims with new and preloved LPs, 45s, cassettes and CDs. Their collection spans genres and decades: where else will you find forest green pressings of “Chet Baker: Live in Sendai, Japan, 1986” alongside headbangers Dead Sara or the 25th anniversary reissue of the Virgin Suicides soundtrack?

It’s always fruitful to browse the shelves at Balfour Books, a cherished second-hand bookstore in a neighbourhood renowned for its indie shops.

Little Italy must-try experiences

Taste of Little Italy is a must-attend. The alfresco festival takes over College Street with live performances by Italo-Canadian musicians, a projection art show and—yes!—food truck fest and street eats.

In late November each year, Little Italy kicks off the holidays with its Cavalcade of Lights, an evening of live music, seasonal snacks and visits with Santa in Lombardi Square (College and Grace Streets).

Getting to Little Italy, Toronto

Little Italy is readily accessible on foot and by bike.
TTC public transit: take the Line 1: Yonge-University subway to Queen’s Park station, then catch the 506 College streetcar westbound to Bathurst Street.
Car parking is available at metered spots, with limited free options on side streets.