Begin by crushing the chocolate sandwich cookies. You can do this by pulsing them in a food processor until you get fine crumbs, or by sealing them in a gallon-size ziplock bag and using a rolling pin to crush them. Set aside for layering later.
In a medium bowl, combine the instant chocolate pudding mix with the milk. Whisk vigorously for 2 minutes, following the package instructions. Allow the pudding to set for 5 minutes until it thickens.
Once the pudding has set, gently fold the whipped topping into the pudding mixture until well combined, creating a light and fluffy filling. I like to fold gently to keep the mixture airy and creamy.
Assemble the dirt cups by adding one tablespoon of the crushed cookies from Step 1 to the bottom of each cup. Top with a layer of the pudding and Cool Whip mixture from Step 3. Continue layering, alternating between crushed cookies and pudding mixture, ending with a final layer of cookie crumbs on top. Repeat this process for each serving cup.
Place the assembled cups in the refrigerator for at least 1 hour to allow the layers to set and the flavors to meld. Chilling also makes the dessert easier to serve.
In a container with a lid, add the shredded coconut, a few drops of green food coloring, and a touch of water. Close the lid and shake until the coconut is evenly colored green, resembling grass.
Right before serving, top each chilled dirt cup with a sprinkle of the green colored coconut from Step 6 and a candy pumpkin for a festive touch. Enjoy your delicious and fun Halloween treat! For a little extra flavor, I sometimes add extra coconut for a bigger 'grass' effect.