These pumpkins are about the size of the cute little real ones you see in the grocery store. This recipe will yield nine pumpkins, but one pumpkin serves about four people.
Before you begin this recipe, if you aren't experienced with making chocolate, read this chocolate making tips page.
Finely chop milk chocolate, then open a can of dulce de leche.
In a bowl, melt the milk chocolate and allow it to cool to about 91 degrees F. Add the dulce de leche and combine. The mixture will be very thick, but the caramel and chocolate must be well-incorporated, so it helps to use your hands. Once well mixed, cover the bowl in plastic wrap and let rest for at least 30 minutes. After unwrapping it, knead it with your hands until smooth, about 30 seconds.
Divide the melted chocolate/dulce de leche mixture into 8-12 pieces, reserving a small handful for the pumpkin stems. Roll each piece into a ball, then flatten slightly and make a small dent in the top center.
Using a knife, cut grooves into each ball, starting at the indentation at the top and going all the way around to the opposite side. Then, use the back of the knife to widen the groves for a more defined pumpkin shape.
Divide the reserved modeling chocolate into 8-12 pieces and roll them into short logs for the pumpkin stems.
Pour confectionery coating into a microwave safe bowl and microwave on high for 40 seconds. Take it out and mix it, even though the wafers will not look like they've melted. Microwave again for 30 more seconds on high, then allow it to cool in the microwave for one to two minutes. Remove it and stir vigorously.
Heat again for 10-15 second increments, stirring after each, until melted. Every microwave is different, but be careful to go slowly as the candy can burn easily. (If your candy coating gets a bit too thick, add some paramount crystals, vegetable oil or coconut oil to thin it out.)
Now is also the time to add pumpkin oil, if you'd like. Add a few drops, then taste. Repeat until you get the desired flavor.
Dip your chocolate caramel pumpkins into the melted candy coating. Line a baking sheet with parchment paper or a nonstick liner.
To ensure a nice coating on the bottoms of your chocolate caramel pumpkins, flip them over and spread a layer of the candy coating on the bottoms before you dip them. Just be sure you only cover the flat surface, or your pumpkins wont have a natural look to them.
Drop one pumpkin into your orange coating, press the pumpkin down into the candy coating and completely submerge.
Use a fork to lift the pumpkin out of the candy coating. Tap the fork on the side of the bowl several times until the excess candy coating falls off the pumpkin. Be sure the dent on the top is apparent; you might need to put your finger in it and push the candy coating out.
Put the pumpkin on your lined baking sheet and smooth out any rough spots made by the tines of the fork. Press a stem into the indentation on top.
Repeat with half of your pumpkins and refrigerate for about 10 minutes until the candy coating is set.
Now you'll have to freshen your candy coating. Reheat it in 10-15 second increments, stirring after each time until melted again. Continue dipping the remaining pumpkins, adding the stems, and chill in refrigerator until set.
Serve for dessert at Thanksgiving, Halloween or any other autumn get-together, or wrap in clear cellophane bags and give as gifts. Store in an airtight container, and they will keep well for at least a month.
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