Here’s what you will need:
1 1/2 bars (3.5 ounces) dark chocolate
1 1/2 cups hot coffee
6 tablespoons bourbon
1 1/2 cups mascarpone
1 cup confectioners’ sugar
2/3 cup heavy cream
1 1/2 teaspoons pure vanilla extract
1/2 teaspoon pumpkin pie spice
1/4 teaspoon cinnamon
1 cup canned pumpkin puree
3 packages (3 ounces) soft Italian ladyfingers (54 cookies)
1 can Reddi-Wip
Begin by coarsely chopping one bar of chocolate. Transfer the chopped chocolate to a large bowl, pour in the coffee and whisk until the chocolate is melted. Then, whisk in 4 tablespoons of bourbon.
In another large bowl, using an electric mixer, beat together the mascarpone, confectioner’s sugar, heavy cream, vanilla, pumpkin pie spice, cinnamon, and remaining 2 tablespoons of bourbon until fluffy. (About 2 minutes.) Add the pumpkin puree and mix until blended and creamy. (At this point, it’s recommended to put this mixture into a large piping bag. However, you can spoon the mixture into your glasses if you do not have a piping bag.)
Begin with 1/3 of the lady fingers. Quickly dip each ladyfinger into the chocolate coffee mixture (about 2 seconds) then arrange them in layers on the bottom of your glasses. Use 3 lady fingers for each layer. Next, pipe (or spoon) a layer of the pumpkin mixture on top of the cookies. Then, grate some of the chocolate onto the pumpkin mixture.
Repeat the layers twice more with the remaining ladyfingers, pumpkin mixture and chocolate. Cover and refrigerate for about four hours. Before serving, top with Reddi-Whip and additional grated chocolate.