These cookies are a Baltimore classic that any Chocolate Lover will enjoy!
Preheat the oven to 375℉ and line baking sheets (you will probably need 2) with parchment paper
Mix butter, salt, vanilla, and baking powder until smooth
Add sugar and mix thoroughly
Beat in egg until creamy
Add the flour and milk a little at a time, but together (for example, 1/2 cup of flour with a little milk and mix on medium, then repeat until done). Here you want to just combine the ingredients, do not overmix
Use a tablespoon and drop the cookies onto the sheet. The dough can be sticky, this is normal. If it is too sticky, dip your fingers into a little flour
Use the back of a measuring cup or the bottom of a glass and wet it with water, then, push the cookies until slightly flattened
Put the cookies into the oven for 10 minutes. They will NOT appear golden or brown, you want them cooked but not brown. They might have a biscuit appearance
Place cookies out to cool completely and start making the icing
Place the chocolate chips, milk, and maple syrup into a microwave-safe dish or on the stovetop. If microwaving, heat for about 60-90 seconds and then stir. Add back to the microwave if needed for 20-30 second periods, stirring between each time. Do this until completely melted. If using the stovetop, stir frequently until melted and stir until smooth
After the chocolate is melted, pour it, the powdered sugar, and vanilla into a mixer or use a hand mixer and mix the ingredients until well combined. You can stir by hand but the powdered sugar can clump
Let the icing cool until it begins to thicken, this is important because otherwise, the icing will just fall right off the cookies
Once cooled a little, dip the cookies into the icing. The icing should be easy to stir with a spoon but thick enough not to be runny.
After dipping all of the cookies allow them to set for a few minutes or put them in the refrigerator for 5 minutes. Then, use a spoon to mound more chocolate on each cookie. You could dip them again but the icing on the cookie will need to be totally set and I find it easier to spoon more on. Repeat the process until you have mounds of chocolate and have gone through most, if not all, of your icing.
Allow icing on the cookies to set for about 10 minutes or longer, and enjoy.