Preheat the waffle iron.
Melt 4 tablespoons of butter and allow to cool.
Whisk together melted butter, eggs, pumpkin, 1 ¼ cups milk, ¼ cup yogurt, 1/3 cup brown sugar, and 3 large eggs until smooth.
In a separate bowl, whisk together 2 cups of all-purpose flour, 1 ½ teaspoon baking powder, 1 ½ teaspoon baking soda, 1 teaspoon cinnamon, and ½ teaspoon kosher salt.
Add dry ingredients to wet ingredients and whisk just until no clumps of flour remain.
Add 1-2 drops of food coloring, if using, and mix until color is fully incorporated.
Once the waffle iron is fully heated, add enough batter to fill the waffle iron. This will vary based on your waffle iron. Cook until the steam stops rising from the machine.
Place finished waffles on a cooling rack.
Allow the waffle iron to reheat before continuing with the next waffle. Repeat until no waffle batter remains.
Place 1 cup of cold whipped cream and 1 teaspoon of maple syrup in a chilled bowl and whip until stiff peaks form 1-2 minutes.
Divide the whipped cream into several bowls, one for each color you will use to decorate.
Add 1 drop of food coloring to each bowl. Use a rubber spatula to blend the color into the whipped cream, being careful not to deflate the whipped cream.
Place the whipped cream into pastry bags or sandwich bags and snip off a corner of each bag.
Use the bags of whipped cream to decorate the waffles. Add candy eyes and other decorations as you see fit.
Serve immediately with more maple syrup.