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Combine 2 cups water, the salt, brown sugar, baking powder, and olive oil in a medium saucepan and bring to a boil over medium heat. Whisk in the flour, stirring constantly just until fully combined, about 30 seconds.
Transfer the dough to a plate, cover with plastic wrap, and let cool to room temperature, about 20 minutes.
Line a sheet pan with parchment paper. On a floured work surface, roll the dough out into a 1/2-inch sheet and use a cookie cutter to stamp out twelve 2-inch circles. Arrange the churros on the baking pan. Cover the pan tightly in plastic wrap and freeze until ready to fry, up to 1 week.
Line a plate with paper towels. Combine the granulated sugar and cinnamon in a small bowl and set aside. Preheat a fryer to 375 degrees F or heat 2 inches of the oil in a large skillet or saucepan over high heat until the oil begins to ripple. Fry the churros, 2 to 4 at a time, for 4 minutes or until golden brown.
Remove the churros from the heat and drain on the paper towel–lined plate for 1 minute to remove any excess oil. Lightly roll the churros in the cinnamon sugar. Place on a rack to cool for at least 5 minutes.
Place a scoop of your favorite ice cream on a cooled churro and press a second churro on top to make a sandwich. Serve immediately.