In a small saucepan over medium heat, combine water, 2.5 tablespoon sugar, salt, and 2 tablespoon vegetable oil. Bring to a boil and remove from heat. Stir in flour until mixture forms a ball.
Heat oil for frying in a deep-fryer or deep skillet to 375°F (190°C). Pipe strips of dough into hot oil using a piping bag. Fry until golden; drain on paper towels.
Combine 0.5 cup sugar and cinnamon. Roll drained churros in cinnamon and sugar mixture.
Place churros in bowls, top with scoops of vanilla ice cream, drizzle with chocolate sauce, add whipped cream, and top with a cherry.