Things to do in Toronto this week: October 25–31

This week the weather does the planning for you. Sunday breaks clear and mild—a 16°C high begging you outside—but by midweek Toronto settles into overcast cool, dipping to single digits Tuesday and Wednesday. Come Thursday, drizzle moves in and sticks through the weekend. It's not a washout, but it is a week that favours indoor culture early and cosy spots when the rain comes.

Start Sunday while the sun's still out. The Sheepdogs hit Phoenix Concert Theatre Thursday at 7 p.m., but they deserve the mention here because a Canadian rock band with four Juno Awards and multi-platinum sales doesn't play the 6ix every month—their roots run deep in Saskatoon, and their catalogue spans two decades of radio staples and deeper cuts that rewards a packed room. If you're catching live rock this week, this is the one. Tickets run the standard Phoenix range; get there early for the pit.

That same Sunday, you've got competing draws. Sienna Spiro plays History Toronto at 6 p.m.—she's a British singer-songwriter who built a following on TikTok sharing viral covers and original work, and History's intimate room suits her stripped-down approach. An hour later, The Army, The Navy (a folk-pop duo out of New York) takes The Mod Club stage at 7 p.m., while over at The Drake, Chanpan and SHEBAD spin electronic and drum-and-bass for the late crowd (19+). That's three solid options on a night when the weather won't stop you.

If comedy's your lane, Greg Fitzsimmons—an Emmy-winning comedy writer and stand-up—performs two shows at Rivoli on Tuesday at 7 p.m. He's been working the circuit for years and brings a sharp, observational edge. Tuesday's chilly and dry, perfect for a basement room and a drink.

Thursday also brings Big Wreck to Pickering Casino Resort at 8 p.m., if you're willing to drive out to Pickering (about 35 km east). They're a Canadian rock institution formed in Boston back in '92, and if you're deep enough into rock to know the name, you know the show's worth the road trip.

Beyond the stages, this week marks a turning point for the city's food scene. Crosstown Craft BBQ—the Texas-style barbecue pop-up that has been selling out in hours—opens its first permanent location on Comstock Road on November 7. That's not this week, but it's worth marking your calendar. More immediately, if you're planning a cosy indoor dinner as the drizzle settles in, PAI on King West remains one of Toronto's best Thai rooms, tight and flavourful; or if you want something more formal, Blu Ristorante Toronto pulls off Italian without pretence. Both work well before or after a show.

One more: Bushido, a new Japanese Kaiseki restaurant, opens Friday inside Casa Loma with an immersive blind dining experience at $350 per person—no menus until service, four rooms, fully committed to the ritual. It's pricey but genuinely singular for the 6ix.

If you've got a single night to give this week, make it Thursday for The Sheepdogs at Phoenix. Canadian rock, a band that actually deserves the room, and drizzle outside that makes the room feel like the only place to be.