Things to do in Toronto this week: September 27 – October 3

This is a week that splits cleanly in two: a clear, mild Sunday that rewards getting out, then a turn toward rain midweek that shifts your plans indoors. The 6ix's calendar reflects that split—some of the season's best live draws on the front end, followed by comedy and theatre that demand a roof.

Start Sunday while the weather holds. Logic, G-Eazy, and Juicy J hit the RBC Amphitheatre at 7 p.m., a three-act lineup built around hip hop and trap that will move the needle for anyone tracking the streaming charts. G-Eazy brings the West Coast trap-rap that defined the mid-2010s, and Juicy J's production legacy runs deep into trap's backbone. The Amphitheatre's outdoor setup means you want the clear skies—Sunday stays mild, hitting 24 degrees in the afternoon with almost no rain risk. Grab dinner before or after at El Catrin on King West; the place moves fast and the mezcal cocktails will warm you on the walk over.

If hip hop is not your lane, Rahat Fateh Ali Khan performs the same evening at Scotiabank Arena. Khan is one of Pakistan's most celebrated singers, rooted in Qawwali, a form of Sufi devotional music that layers spiritual weight into every phrase. This is not a casual show—it is one of those rare nights when a living master of his form comes through, and the Arena will reflect that reverence.

Theodore Katzman, the founding multi-instrumentalist of Vulfpeck and solo artist, takes the Great Hall that same Sunday at 7 p.m. Funk and precision musicianship in a room half the size of the Amphitheatre means you actually see the work. The Psycodelics play the Monarch Tavern at the same time for 27 dollars—a lower-stakes Sunday night if you want to feel out a new room.

By Wednesday the forecast turns. Rain arrives Thursday through Saturday, with Friday the wettest day of the week. That is when you move indoors with conviction.

John Cleese, the English actor and Monty Python architect, takes the Elgin and Winter Garden Theatre Centre for two shows September 30 and October 1. Cleese emerged from Cambridge Footlights in the 1960s and first broke through at the Edinburgh Festival Fringe before writing and performing on The Frost Report—credentials that place him among the comedians who actually shaped modern comedy. This is not nostalgia tourism; this is watching a structural mind work a room. The theatre's position at Yonge and Dundas puts you near estiatorio Milos Toronto for a pre-show meal if you want fine dining—the Cantonese kitchen at Mott 32 just took Canada's best Chinese restaurant honours for 2026, but Milos' Mediterranean grounding feels right before an evening of British wit.

Thursday and Friday rain means cozy indoor dining matters. Millie Desserts, the mille crepe institution that shuttered all three locations by 2024, has relaunched from a new Adelaide Street window downtown. Slices and custom orders from a tight spot: the kind of neighbourhood reopening that makes people actually change their week when the weather turns sour.

If you have a single night to commit, slip into the Elgin and Winter Garden on Wednesday or Thursday to watch Cleese—a working master of his form in a theatre built for exactly this kind of attention.