Preheat oven to 250 degrees F. Line baking sheet with parchment paper and spray with cooking spray. Set aside.

Pour 1 cup apple cider into a medium saucepan and bring to a boil over high heat. Continue to cook apple cider until reduced to 2 ½ tbsp, about 10 minutes. Remove from heat and let cool.

Combine the reduced apple cider with ⅓ cup cream and spices, from cinnamon - allspice. Set aside.

Measure 2 ½ tablespoon cream in a 1 cup measuring cup. Add enough water to fill the measuring cup up to the ½ cup line. Combine with sugar and corn syrup in a heavy saucepan. Cook over low heat until the sugar dissolves and the syrup reaches 234 degrees F.

Remove from heat and gradually add the cream and cider mixture to the syrup. Add the butter and stir until the butter has melted. Bring back to heat over low and cook until 248 degrees F, stirring frequently. Remove caramel from heat.

Meanwhile, pop the popcorn. Discard any unpopped kernels. Transfer popcorn to prepared baking sheet, pouring the caramel on top. Stir to coat the popcorn with the caramel. Bake in the oven for 45 minutes, stirring every 15 minutes. Remove popcorn from oven.

Immediately transfer popcorn to a clean parchment paper that has been sprayed with cooking spray. Let cool. Break popcorn into pieces.

Combine sugar with cinnamon. Sprinkle on top of the popcorn.

Melt chocolate in the microwave, stirring every 15 seconds until melted. Drizzle on the popcorn and let chocolate harden. Serve.