Combine the unwrapped caramels and heavy cream in a small saucepan. Cook over low heat, stirring occasionally, until the caramels are completely melted and the mixture is smooth. Let the caramel cool for about 15 minutes.
In a large mixing bowl, beat the softened cream cheese until light and fluffy.
Add the pumpkin puree, brown sugar, vanilla extract, and pumpkin pie spice. Beat until thoroughly combined and smooth.
Gently fold in the thawed whipped topping with a rubber spatula until evenly incorporated.
Pour enough cooled caramel sauce into the bottom of a serving bowl to cover the base.
Spoon half of the pumpkin cheesecake mixture over the caramel and gently smooth the surface. Drizzle with more caramel sauce, reserving some for the top.
Add the remaining pumpkin cheesecake mixture and finish with the remaining caramel sauce.
Serve immediately with apple slices, graham crackers, gingersnaps, pretzels, or your favorite dippers.