In a large mixing bowl, combine the pumpkin puree, softened cream cheese, powdered sugar, and vanilla extract. Using an electric mixer, beat the mixture on medium speed until it becomes smooth and fluffy, approximately 2-3 minutes.
In a separate bowl, pour the heavy cream and use a whisk or an electric mixer to whip it until stiff peaks form. This should take about 3-5 minutes.
Gradually fold the whipped cream into the pumpkin mixture using a spatula, being careful to maintain the light and airy texture until fully combined.
Begin layering your cups or small jars by adding a generous layer of crushed chocolate cookies at the bottom. This will represent the dirt foundation of your cups.
Next, evenly spread a layer of the creamy pumpkin mixture over the crushed cookies, ensuring it covers them completely for even flavor distribution.
Repeat the layering process: add another layer of crushed cookies, followed by a second layer of the pumpkin mixture.
For the final touch, top the last layer with a generous sprinkle of crushed cookies to achieve a dirt-like appearance.
Take the gummy worms and creatively place them on top so they look like they are crawling out from the dirt.
If desired, add a colorful sprinkle of candy corn on top for a sweet treat and visual appeal.
To finish, garnish with fresh mint leaves for a vibrant pop of green that enhances the presentation.
Notes
Optional candy corn and mint leaves can enhance presentation.