The patio at Bellwoods Brewery in summer on Ossington Street


Arguably one of the city’s trendiest strips, Ossington is hugely popular with the under-30 crowd. It’s the spot for a great night out. You can make a reservation in advance or walk the main drag and hit a great spot to settle in for the evening. If live music is more your jam, stop in at The Dakota Tavern for nightly Southern-style live music.

Don’t miss:

  • Bellwoods Brewery, which specializes in puckeringly sour and tartly hoppy ales
  • Taking the kids for the city’s most popular ice cream sandwich at Bang Bang Ice Cream & Bakery
  • A luxurious spread of Latin American-by-way-of-Asia dishes at Foxley, a favourite of local foodies 
  • Stopping at Telegramme Prints and Custom Framing for a retro poster, or Rotate This for must-have vinyl records
  • The laneways leading off Ossington Avenue, where you’ll spot some of the city’s coolest art

BOUNDARIES: Ossington Avenue, between Dundas Street West and Queen Street West. 

PUBLIC TRANSIT (TTC): 501 streetcar from downtown. Or Ossington subway station, then take the 63 bus southbound.

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The Westside is the liveliest and trendiest part of the city. It’s open all hours, and the streets are lined with hip restaurants, bars and all manner of local boutiques.