Place the ice cream insert in the freezer a full 24 hours before making your ice cream.
Whisk together the cream, milk, brown sugar, bourbon and cinnamon together in a large liquid measuring cup and refrigerate until cold, about 30 minutes.
Turn your ice cream machine on and pour in the cream mixture. Churn until the mixture looks slushy like soft serve, about 15 minutes. Remove the canister from the ice cream maker and place in the freezer for several hours until firm enough to scoop.
Divide the ice cream amongst 4 ice cream bowls and top with caramel sauce, crushed gingersnaps and Maple Whipped Cream.
Maple Whipped Cream:
Whip the heavy cream in a cold bowl with an electric hand mixer until it looks thick. Add the powdered sugar and maple syrup and continue beating until medium peaks appear.