Halloween Dirt Pudding Cups with RIP Tombstones

Halloween Dirt Pudding Cups / Mini Trifles

These clear-cup dirt puddings have two fluffy chocolate layers divided by a dark cookie-crumb stripe. A mound of cookie “dirt,” an upright RIP tombstone, a candy pumpkin, and a gummy worm turn each cup into an edible graveyard.

Instant pudding and whipped topping make the filling without cooking. Let the pudding thicken before folding in the topping so the layers stay distinct, then chill the cups before decorating. Save the exposed crumbs and candy for just before serving so the dirt looks loose and the tombstones stay firm.

Ingredients for 8 Dirt Pudding Cups

• 2 packages instant chocolate pudding mix (3.9 ounces each; about 220g total)
• 3 cups cold whole milk (720g)
• 1 tub frozen whipped topping (8 ounces), thawed (about 225g)
• 30 chocolate sandwich cookies, finely crushed (about 3 cups crumbs; 360g), divided
• 8 oval butter cookies or Milano-style cookies
• About 2 tablespoons black decorating icing
• 8 small edible orange pumpkin candies
• 8 to 16 gummy worms

You’ll also need eight clear, straight-sided 8-ounce dessert cups. Use instant pudding mix; cook-and-serve pudding requires a different method and is not a direct substitute.

How to Make Halloween Dirt Pudding Cups

1. Make the tombstones: Pipe “RIP” in black icing on the upper half of each oval cookie, leaving the lower half clear for inserting into the pudding. Set aside at room temperature until the icing is firm enough not to smear.
2. Crush the cookies: Pulse the chocolate sandwich cookies in a food processor, or crush them in a sealed bag with a rolling pin, until mostly fine and dark. Reserve 1 cup of crumbs in an airtight container for the tops; use the rest for the middle layers.
3. Thicken the pudding: Whisk the instant pudding mix with the cold milk for about 2 minutes. Let stand until thick, following the package setting time, usually about 5 minutes. The whisk should leave tracks in the pudding; it should not pour like a thin sauce.
4. Fold in the whipped topping: Gently fold it into the thick pudding until no white streaks remain. If the filling is too soft to hold a layer, refrigerate it for 15 to 20 minutes before filling the cups.
5. Build the layers: Pipe or carefully spoon pudding into each clear cup. Add a thin, even layer of the unreserved crumbs, then a second, taller pudding layer. Keep the dark stripe visible around the sides and leave about 3/4 inch of space at the top. A piping bag or zip-top bag with a corner snipped helps keep the cup walls clean.
6. Chill: Loosely cover the undecorated cups and refrigerate for at least 1 hour, until the top pudding layer is firm enough to support a cookie.
7. Finish the graveyards: Just before serving, spoon the reserved crumbs onto each cup in a loose, uneven mound. Insert a RIP cookie near the back, pushing its undecorated end about 1/2 inch into the chilled pudding beneath the crumbs rather than resting it on the loose dirt. Nestle a pumpkin candy and at least one visible gummy worm into each mound. Serve chilled.

Time: About 30 minutes of preparation, plus at least 1 hour of chilling. Yield: Eight individual 8-ounce cups.

Make-Ahead and Storage

Make the RIP cookies and crush the sandwich cookies up to 2 days ahead. Once the icing has set, keep the tombstones and crumbs separately airtight at room temperature. The layered pudding cups can be covered and refrigerated up to 1 day ahead; add the top crumbs, tombstones, pumpkins, and gummy worms just before serving.

Refrigerate finished leftovers, covered, for up to 3 days. The exposed crumbs will soften, and the gummy worms may become firmer. Do not reheat. Freezing is not recommended for these pudding-only cups because the filling and decorations may lose their intended texture.

Optional Brownie Mini Trifles

For a more substantial version, add up to 1 1/2 cups of small cubes of fudgy chocolate brownies beneath the middle crumb stripe. Keep the clear-cup layers and graveyard decorations, and assemble no more than a day ahead; the brownie pieces soften as they sit. Use only edible decorations, not plastic props.

Nutrition

Approximate per cup, based on 8 servings: 570 calories, 7g protein, 19g fat, and 95g carbohydrates. Approximate per 100g: 255 calories, 3g protein, 8g fat, and 42g carbohydrates. Values vary with the brands and sizes of the cookies, candy, pudding mix, and whipped topping.