In a mixing bowl, whisk together the chocolate pudding mix and cold milk until the mixture thickens and becomes smooth, about 2-3 minutes. This creates a rich, creamy pudding base.
Spread a layer of crushed cookies evenly at the bottom of the baking dish, forming a crumbly 'dirt' base.
Pour the prepared chocolate pudding over the cookie layer, smoothing it out with a spatula to create an even, glossy surface that resembles soil.
Sprinkle additional crushed cookies on top of the pudding to add texture and enhance the dirt-like appearance.
Decorate the surface with colorful gummy worms, arranging them to appear as if they're crawling out of the dirt.
Cover the dish with plastic wrap or foil and refrigerate for at least 2 hours, allowing the pudding to set and flavors to meld.
Once set, sprinkle more crushed cookies around the edges for extra dirt effect if desired, and add additional gummy worms for extra fun.
Serve the Halloween Dirt Cake in bowls or cups, ensuring each portion has plenty of the crumbly dirt and playful worms for a messy, fun treat.