Pop the popcorn, removing any unpopped kernels. Set aside in a large bowl
In a heavy 6 quart saucepan add the butter, brown sugar, and corn syrup.
On medium- high heat, bring these ingredients to a boil. While stirring, slowly add the sweetened condensed milk.
Insert candy thermometer and let it cook, softly boiling, almost constantly stirring, until mixture reaches soft ball stage (235°F at sea level). Err on the side of undercooking – if it gets too hard, it’s harder to eat.
About 2 degrees before it reaches the correct temperature, add in the salt, vanilla, and pumpkin spice. Stir.
Pour over the popcorn, carefully, and stir with a silicon spatula until the caramel has covered the popcorn evenly.
Butter your hands and form caramel popcorn into balls – about the size of a tennis ball (or any size you’d like.) Be careful as this can be hot! Try to work quickly.
Insert the lollipop sticks and set the balls onto a cookie sheet with waxed paper.
Melt the chocolate melts and drizzle over the tops of the popcorn balls. Add sprinkles and serve!