Skippy's

The Best Restaurants On Staten Island

"If you need some proof that Staten Island is a small town, head to Skippy’s, a legendary hot dog truck currently parked on Hylan Boulevard. Open since 1962, the line is always full of people who went to junior high school with each other—and also the proprietress, Dawn, who inherited the truck from her parents, and will call you “sweetie” a minimum of three times, but probably more like five. Order anything that involves Dawn’s bright red, homemade chili—we like the Wally Dog, with cheese, chili, and sauerkraut—and then sit on a bench, and drink a Dr. Brown’s black cherry soda." - willa moore