drake in toronto

Drake just showed up at a Toronto bar and reportedly bought everyone shots

It seems like Toronto's favourite hometown celebrity, Drake, has been having quite the busy summer in the city.

The Grammy-winning singer was spotted making a surprise appearance at Cherry's High Dive over the weekend, the Wellington Street West hotspot known for its casual dive-bar-meets-pizza-tavern vibe.

Although a pleasant surprise for patrons at the bar that night, Drake's latest appearance is just the latest in a string of viral appearances around the 6ix. And while Cherry's isn't typically considered one of the city's major celebrity hotspots, that's arguably what makes the sighting so on-brand for Drake.

The multi-platinum-selling rapper, dressed in a casual red T-shirt and blue jeans, reportedly bought a round of shots for everyone in the venue, according to patrons there at the time.

This isn't the first time in recent weeks Drake has sent Toronto fans into a frenzy. His recent viral appearance at the CNE, strolling the midway dressed as Iron Man, came just days after he reportedly rented out all of Casa Loma for a date night with online personality Lin Lamar, better known by fans as Pinkchyu.

Drake's latest viral moments follow a string of bizarre album promotional stunts that made waves in the city ahead of the May 2026 drop of the Iceman, Maid of Honour, and Habibti albums.

I think it's safe to say that there's never a dull moment when Drake is in Toronto.

Lead photo by

@mrkrilliansexton


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