Best of the City 2026: Best Spot to Be Wild About Harry

Photo by Sean Timm

If your wee ones are under the spell of all things Hogwarts, we’ve got the spot that will transport them to The Wizarding World this fall. Every Halloween, the aptly named Diagon Alley in North Oak Park between 33rd and 34th streets (about a block down from the Guild Theater) is home to a magical trunk-or-treat tailgating event, where little Harry Potters and Hermione Grangers can score sweet somethings against a backdrop of murals and installations depicting everything from Platform 9 3⁄4 and the Hogwarts Express to Dobby’s private residence and Eeylops Owl Emporium. The themed passageway is the handiwork of area artists like Thomas Sumpter and Aimee “Phoenix” Phelps, who help host this neighborhood holiday bash, also featuring an illuminated haunted maze in Sumpter’s yard (33rd Street and Diagon Alley) and Phelps’ immersive “Oak Park Halloween House” attraction (33rd Street and 4th Avenue) boo-tified with fire dancers, a skull arch, a wall of jack-o-lanterns and a cauldron of candy. Consider us enchanted. 

READ MORE: Pick up our Fall Issue for the full Best of the City 2026 list