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• Tonight is the Reader's Fall Cocktail Challenge; get more info here.
• Your dining agenda for the next few months may be set in this epic south-side taco survey by Titus Ruscitti at Serious Eats Chicago. It makes you realize how vast and undiscovered the Mexican food scene in this town remains—even as an assiduous explorer of south-side taquerias, I felt like Sandra Bullock staring into the 3-D void of space when confronted with the galaxy of places I've never heard of, or have actually been to without ordering what is apparently the thing to have (the pastor at Don Cuco on 47th was pretty lame—who would have guessed that the shrimp taco there would turn out to be glorious?)
• Feel like dessert, followed by dessert and more dessert? Hit the Chicago Fine Chocolate & Dessert Show's Room for Dessert dinner on October 14 at Storefront Company and get desserts paired with savory bites from pastry stars like Patrick Fahy (Sixteen), Elissa Narow (Perennial Virant), Thomas Raquel (Acadia), and others. A portion of proceeds will go to Icing Smiles, which provides celebration cakes and other treats to families impacted by the critical illness of a child. Tickets are $50 here.
• Food Network will be casting "America's greatest home cooks" for a new show pairing home cooks and celebrity chefs next Saturday, October 12, at the Wooden Spoon in Andersonville. More info here.
• Shaw's Oyster Fest is a staple of the downtown food-party scene, and it's celebrating its 25th anniversary this year with Buddy Guy headlining. It kicks off with an oyster dinner Wednesday featuring chef Sandy Ingber of New York's Grand Central Oyster Bar (which is celebrating its own 100th anniversary this year), with special guest chefs Giuseppe Tentori (GT Fish & Oyster) and Brian Huston (the Publican). The main festival runs the week of October 14 through 18; check out more about it here.