Pumpkin Bread at Birchwood: Birchwood’s chocolate chip pumpkin bread is a lighter alternative to heavy gourd-inspired treats. The sugar sprinkled topping adds a nice crunch to the outer layer. And because this little kitchen aims to use local, seasonal produce whenever possible, you can bet the pumpkin isn’t coming from some can.
Birchwood Kitchen: 2211 W. North Avenue,
Chicago, IL 60647 (map); 773-276-2100; birchwoodkitchen.com.
Pumpkin Spice Gelato at Black Dog: Shop owner Jessica Oloroso sells her goods at top Chicago restaurants like Girl and Goat (she trained under owner and Top Chef winner Stephanie Izard) and Socca. At her Ukrainian Village shop, which opened last year, she serves up this seasonal treat come fall. It’s decadently creamy and perfectly spiced, like pie turned ice cream.
Black Dog: 859 N. Damen Avenue, Chicago, IL 60622 (map); 773-235-3116; blackdogchicago.com.
Pumpkin Whoopie Pie at Bleeding Heart Bakery: This punk rock-themed bakery prides itself on using organic, sustainable goods—even the cooking oil—for all of its dishes and pastries. For this whoopie pie, two large pumpkin cakes bookend an ample glob of cream cheese frosting sprinkled with walnuts. The cakes are extremely moist and buttery, while the filling is lightly whipped. And be sure to bring your sweet tooth—these pies are huge!
Bleeding Heart Bakery: Multiple locations. thebleedingheartbakery.com.
Pumpkin Pie at Hoosier Mama: A pumpkin dessert list would be incomplete without this iconic fall treat. And when it comes to pies, Hoosier Mama owner Paula Haney has few rivals. The buttery crust is flaky and subtly sweet—a compliment to the pie’s silky consistency. The pie itself is spicier than most, which could be attributed to a pinch of pepper in the batter. It adds just the right amount of kick to the to this sweet treat.
Hoosier Mama: 1618 1/2 Chicago Avenue, Chicago, IL 60622 (map); 312-243-4846; hoosiermamapie.com.
Pumpkin Spice Cupcake at Alliance Bakery: Chicago is witnessing an influx of trendy, coastal cupcake boutiques (Sprinkles, Magnolia’s, Crumbs), but they’ve got stiff competition from Alliance Bakery, which has been a Chicago dessert destination for more than a century. The Wicker Park icon whips up a tasty pumpkin spice cupcake that’s moist, crumbly, and subtly spiced. And the cream cheese frosting is lopped on thick, but isn’t overwhelmingly sweet.
Alliance Bakery: 1736 W. Division St., Chicago, IL 60622 (map); 773-278-0366; alliance-bakery.com.
Pumpkin Pie and Pumpkin Pecan Fudge at Windy City Sweets: For almost 30 years, this Lincoln Park candyland has churned out handmade chocolates and fudge, including fall’s popular pumpkin fudge. Both the pumpkin pie and pumpkin pecan varieties have a smooth, creamy consistency. They pack a sweet, rich flavor, though, so it’s best to nosh in small pieces.
Windy City Sweets: 3308 N. Broadway Street, Chicago, IL 60657 (map); 773-477-6100; windycitysweets.com.
Vegan Chocolate Pumpkin Cheesecake at The Chicago Diner: Vegan Cheesecake? One bite of the Diner’s confection will quell any skepticism about this oxymoronic dessert. Bakers use a whipped tofu and soy-based mock 'cream cheese' that exactly replicates cheesecake’s velvety texture. The pureed pumpkin and spices mask any aftertaste that many find with soy products, while a clovey crust and chocolate topping make the pie unique to the North Side diner.
The Chicago Diner: 3411 N. Halsted Street, Chicago, IL 60657 (map); 773-935-6696; veggiediner.com/wp.