New York has Carnegie, London has the Royal Albert Hall, and Toronto has Massey Hall, a stage where legends are made. First opened in 1894, the 2700-seat theater played a crucial role in the rise of Canadian rock royalty like Neil Young. Today it’s a grand yet intimate venue where Janelle Monáe and Mitski opt to play multi-night stands instead of trading up to arenas. In 2023, it expanded to include an adjacent 500-capacity space, TD Music Hall, to nurture the Massey headliners of tomorrow.

Built in 1919, the Danforth has retained the classic architectural details of an old-school neighborhood bijou, but the Riverdale venue adapts to the occasion. When veteran alt-rock acts like Sparks come to town, it feels like a classy sit-down theater, but when the unruly likes of IDLES roll in, floor seating is removed to make way for the mosh pit. (Those who’d rather not fend off crowd-surfers can watch the mayhem from the balcony.)

You can tell a Torontonian’s age based on what they call this building at 1 Front Street East. Since opening in 1960, the venue in the St. Lawrence Market has changed names many times over, settling on Meridian Hall in 2019. While some of its seats were torn out by rowdy fans at an infamous Clash show in 1979, Canada’s largest soft-seat theater remains a midcentury modernist marvel—the ideal place to see icons like Robert Plant, Nick Cave, and Kraftwerk.

Each August, the Canadian National Exhibition grounds transform into Canada’s biggest fair, but the Queen Elizabeth Theatre brings A-list entertainment to the site year-round. This beautifully preserved midcentury auditorium first opened along the Ontario lakefront in 1956. Since being renovated in 2019, it shifts between an 1140-seat theater (for heritage acts like Lucinda Williams) and a 2400-capacity GA space (for big pop draws in the vein of Ed Sheeran).

When it opened in 2021, HISTORY became an instant fixture on Toronto’s concert map, thanks in no small part to Drake, who helped design the flashy space. With its generous sight lines and sharp-dressed staff, this venue in The Beaches has a VIP vibe, even if you haven’t forked out for upper-level table service tickets. Beyond its steady stream of zeitgeist-y rap, R&B, and pop acts (Lil Yachty, Brent Faiyaz, Rina Sawayama), it’s also become part of Drake’s OVO Fest ecosystem.

Hidden at the end of an industrial street in the Port Lands district, Rebel’s tough to get to without a car. But once you’re there, Toronto’s largest club is a futurist feast for the senses, with trippy LED-lined walls and an outdoor terrace with a postcard view of the skyline. Headliners are a mixed bag: You might catch a DJ set from Travis Scott, a performance from OVO’s dvsn, or a band like Cannibal Corpse who wouldn’t otherwise be caught dead in a bottle service club.

Few venues have altered Toronto’s cultural landscape as dramatically as the Drake (no relation to the rapper). The hotel’s history dates back to 1890, but its modern era began in 2004 when it was reimagined just in time to catch the indie-sleaze wave and shift the city’s nightlife epicenter to downtown’s western fringe. Its small, cabaret-like basement venue, the Underground, has been a launchpad for game changers like M.I.A. and Billie Eilish, who performed here long before they hit stardom.

The downtown venue’s curved glass exterior makes it one of Toronto’s boldest architectural landmarks. The inside is equally striking, with balconies that ripple toward the venue’s crown jewel: a towering pipe organ that cost $650,000 (in 1982 dollars) to build. It’s primarily home to the Toronto Symphony Orchestra but also welcomes visiting virtuosos like Yo-Yo Ma as well as contemporary music acts (Sigur Rós, Kamasi Washington) who might be looking for some extra pomp with their circumstance.

The century-old Masonic temple has a hallowed rock history that dates back to the late ’60s, when it became known for showcasing cutting-edge bands (Led Zeppelin, Grateful Dead, The Ramones, The Cure) before they graduated to arenas. The Yorkville venue was converted into a studio for CTV and MTV Canada in the ’90s, but in 2023, it reopened its doors as a concert hall, hosting rising rockers like Black Country, New Road and hometown heroes like Broken Social Scene.

The main concert space inside Toronto’s Royal Conservatory of Music is an architectural gem, with warm wood paneling and a canopy of carved oak tendrils rippling over the stage. The sleek design complements Koerner’s impeccable sound design: The pianist Lang Lang called it “the best acoustic hall in the world.” But the theater doesn’t limit itself to classical music. Since opening in 2009, it has hosted jazz trios, folk festivals, soul music tributes, and more.