Mix sugar, condensed milk and vanilla extract in a bowl until it just comes together. Pour out on to powdered sugar coated parchment paper and knead until a smooth dough forms. Add more powdered sugar as needed if the dough is too sticky or add a teaspoon of condensed milk if too dry. The dough should hold its shape and not spread out when the right consistency is reached. It'll be almost on the dry side.
Weigh and divide into 3 equal portions. Set aside one dough and leave it for the white layer. Add maple extract to another portioned dough to make the brown layer. You will need to add more powdered sugar after the extract is incorporated to reduce the stickiness caused from the added liquid. Add orange food coloring to the remaining portion of dough and add more sugar as needed until the color is incorporated.
Roll out dough and cut out twelve 1-inch circles with a cookie cutter. Repeat with each layer. Stack layers in candy corn color order. Use the same cookie cutter to cut through stacked layers to level and clean up the sides. Stick a toothpick into each to get ready for dipping.Two ways to coat: 1. Melt milk chocolate and dip each candy filling in chocolate to coat and place on parchment paper to harden, remove toothpicks. Then melt the orange chocolate and fill up mold ⅓ to ½ full and then press the hardened chocolate coated candy filling into the orange chocolate. Allow to harden and remove from mold. Or you can coat them this way...2. Melt the orange melting chocolate and pour into pumpkin molds, painting sides of mold and allow excess to drip out and let the orange chocolate harden. Then dip the candy filling in milk chocolate and immediately place into the prepared pumpkin molds. Allow to harden, remove toothpicks, and remove from molds. Optional: Use the melting chocolate to fill in the jack-o-lantern details, but if you're like me and suck at detail work with melting chocolate, I dusted them with black cocoa powder and painted the faces with it too for a rustic aged effect.