"Since 1937, Jim Dandy Drive-In on Sandy has been a destination spot for car nerds, thanks to its history of hosting illegal drag races in the mid-20th century. The space is absolutely plastered with newspaper clippings and photos of historic Portland, including its hot rodders. Expect the standard diner fare, including milkshakes with more than 100 flavor combinations and a burger former Simpsons showrunner Bill Oakley called “the best old-school cheeseburger” he’s had." - Rachel Pinsky