Things to do in Toronto this week: June 14–20

This week the weather does you no favours — heavy rain Sunday, scattered showers through Thursday, with only Friday offering a real break. Plan accordingly: lead with the indoor marquee events, pivot to patios and walks when the forecast clears, and use the wet stretches to explore the dining scene and neighbourhoods on foot.

Sunday is your busy day indoors. British and Irish comedian Jimmy Carr plays Scotiabank Arena at 7 p.m., and at 5:30 p.m. the same evening Dan + Shay, the American country music duo, perform at The Opera House as part of NXNE's Billboard THE STAGE series. Dan + Shay have released six albums through Warner Records Nashville and built a career on contemporary country and country pop; if you want a solid country evening before or after Carr's sharper observational comedy, this is your window. Earlier on Sunday, Minneapolis indie group TWINSICK plays Cabana Pool Bar at 1 p.m., and Seattle-based indie folk singer Noah Gundersen takes the Horseshoe Tavern at 7:30 p.m. — a smaller, looser evening if arena-scale crowds don't appeal.

By Tuesday the rain lightens slightly, though it'll still be cool. That's when the Marcus King Band brings their American rock sound to Massey Hall at 8 p.m. — South Carolina-born, formed in 2013, and a natural fit for the hall's intimate scale. Wednesday brings another rain window (63% chance), making it a night for covered venues; Arkells, the Hamilton-born Canadian rock band on the Universal Music Canada roster, play Lee's Palace at 7 p.m. — a hometown band in a room they know well.

Friday clears meaningfully. That's your moment to pivot outdoors or to a place with serious natural light. If you're hunting an exceptional dinner with a view or a civilized cocktail, estiatorio Milos Toronto — fine dining, serious wine list — becomes a smart play that night when the weather actually cooperates. The Keg Steakhouse + Bar on York Street is equally solid for a drink and a meal with more breathing room than the week's indoor rush.

Beyond the stages, the city has been moving fast. Playa Bowls, the California acai bowl chain, opens its first Canadian location at The Well on Thursday — the first 100 customers get a free bowl, so if you're in that neighbourhood and keen on the thing, timing matters. Hayden's Cheesesteaks, launched by Toronto corporate lawyer Max Solomons to honour his late father's passion for Philadelphia sandwiches, has been drawing obsessed lines; a solid lunch pick if you're downtown and want something beyond the usual.

One thing worth holding in your mind: FIFA World Cup 2026 is coming to Toronto this summer, and matches will flood the city's stadium from mid-June onward. The full schedule lives at /toronto/fifa-world-cup — bookmark it now because the logistics will matter once the matches start.

If you've got one night to give this week, spend it on Jimmy Carr at Scotiabank Arena on Sunday — a world-class comedian in a room built for scale, dry wit before the rain really settles in.