Gather all ingredients and equipment, setting everything within reach for smooth layering.
Using a whisk, beat the heavy cream with sugar and vanilla until soft peaks form, creating a light, airy whipped cream that smells sweet and looks fluffy.
Gently fold in the pumpkin puree into the whipped cream, mixing just until combined for a smooth, vibrant orange cream.
Start assembling the trifle by spreading a layer of crumbled cookies at the bottom of the glass dish, creating a crunchy base that crunches as you layer.
Spread a generous layer of pumpkin whipped cream over the cookie crumbs, smoothing it out with a spatula for an even surface.
Drizzle caramel sauce over the cream to add a smoky sweetness and visual shimmer, then add a handful of blackberries for a dark pop of color.
Add another layer of crumbled cookies, followed by more pumpkin whipped cream, repeating the layering process to build depth and contrast.
Decorate the top with creepy candies like candy eyeballs, gummy worms, and fruit slices to make the trifle spooky and fun.
Finish with a final drizzle of caramel sauce and a few extra berries for color and shine, creating a spooky, layered look.
Refrigerate the assembled trifle for at least 2 hours to let the layers set and flavors meld, making it ready for serving.
Serve chilled, revealing the colorful, spooky layers that will delight guests and add a festive touch to your Halloween celebration.
