Insert lollipop sticks one-third of the way into each apple. Line a baking sheet with parchment paper and coat the parchment with cooking spray.
Combine the sugar, corn syrup and 1/4 cup water in a small saucepan; bring to a boil. Reduce the heat to medium and add the orange food coloring. Continue cooking, swirling the pan but not stirring, until a candy thermometer registers 290 degrees F, about 10 minutes; remove from the heat. Working one at a time, dip the apples into the candy, then twirl over the pan to let the excess drip off, keeping your fingers out of the way of the hot candy coating. Transfer to the prepared baking sheet and let stand until set, about 5 minutes.
Put the chocolate in a large microwave-safe bowl and microwave in 30-second intervals, stirring, until smooth. One at a time, hold each apple over the bowl and use a fork to drizzle with chocolate, turning to coat around the base of the apple. Return to the baking sheet; let set, about 5 more minutes.