Chocolate Half Moon Cookies
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These Chocolate Half Moon Cookies are a New York cookie that’s soft, fluffy, and my favorite chocolate cookie of all times. The bottom of the cookie becomes the top that’s frosted half vanilla frosting and half chocolate frosting.

So, I admit I’m somewhat obsessed with making perfect half moons. I just want a delicious recipe that will satisfy my craving of Wegman’s half moons. I seriously hate when you find something that you crave often and then BOOM! You have no access to it anymore. The heart and taste buds want what they want. It just can’t be helped. As I was searching the web for an awesome recipe, I came across these pretty babies.
I was hoping for a gooey fudge, but this fudge was satisfying. It hardened quickly once it was removed from the double boiler. The made it easy to frost the other half of the cookie. That was pretty great. I guess I didn’t realize how much of a pain it is to frost these cookies. The cake was soft and chewy, but definitely a little crumbly. Considering the cookies were gone, all 23 of them, in a matter of a few days I think we were able to deal with it. 23 monstrous cookies. They were the same size as my son’s head.

Regardless of whose recipe, the white side is my favorite. I’m probably weird, but I don’t care for chocolate on chocolate. I also don’t care for vanilla on vanilla. I powered through it.. time and time again though. 😀 I always manage to put my differences aside for a baked good. That’s probably why I’ve gained all my weight back that I worked so hard to lose last year. Needless to say, I’m back on the treadmill starting this week. Oh, just in case my generous husband is reading, I could use some good running shoes. I have blisters on my little toes.



Chocolate Half Moon Cookies
SAVE THIS RECIPE
Ingredients
Cookies
- 2 1/4 cups granulated sugar
- 1 cup butter, cubed
- 3/4 cup unsweetened cocoa powder, sifted
- 1/4 teaspoon salt
- 2 large eggs
- 1 teaspoon vanilla extract
- 3 3/4 cups cake flour
- 3/4 teaspoon baking powder
- 2 teaspoons baking soda
- 1 1/2 cups whole milk
Icing
- 1/2 cup butter, room temperature
- 1/4 cup shortening, butter flavored
- 3 1/2 cups powdered sugar
- 3 tablespoons whole milk
- 1/2 tablespoon vanilla extract
- 1/8 teaspoon salt
Fudge Icing
- 2 ounces dark chocolate chips
- 2 ounces milk chocolate chips
- 2 tablespoons butter
- 2 1/4 cups powdered sugar
- 1 tablespoon light corn syrup
- 1 teaspoon vanilla extract
- 1/8 teaspoon salt
- 4 tablespoons hot water
Instructions
- Preheat oven to 350 degrees F. Line cookie sheets with parchment paper.
- In a stand mixing bowl, add 2 1/4 cups granulated sugar and 1 cup butter. Mix with a paddle attachment on medium until light and fluffy. Scrape down the sides.
- Add in the sifted 3/4 cup unsweetened cocoa powder and 1/4 teaspoon saltMix on low until combined.
- Add in the 2 large eggs and 1 teaspoon vanilla extract. Mix on low until incorporated into the wet mixture. Scrape down the sides.
- In a separate bowl, sift the 3 3/4 cups cake flour, 3/4 teaspoon baking powder, and 2 teaspoons baking soda.
- Add half of the flour into the wet mixture and beat on low to avoid a flour shower.
- Once the flour is combined into the wet mixture, add half of the 1 1/2 cups whole milk. Continue beating on low. Scrape down the sides once the milk is incorporated.
- Repeat with the other half of the flour and mixing.
- Repeat with the other half of the milk and mixing. Scrape down the sides and bottom of the bowl and stir in any remnants.
- Using a large 3 tablespoon ice cream scoop/cookie scoop, scoop the dough and place 2 inches apart on the cookie sheet. I only put 5 on my cookie sheet.
- Place in the oven for 15 minutes or until the centers are set. The times will vary depending on the size of the cookies just make sure the center of the cookie is the same color as the edges of the cookie and not darker.
- Let the cookies cool on the cookie sheet for 10 minutes before placing the cookies on the cooling rack.
Icing
- In the mixing bowl, add in the 1/2 cup butter1/4 cup shortening. Mix until the two are combined. Scrape down the sides.
- Add in half of the 3 1/2 cups powdered sugar and mix on low. Scrape down the sides.
- Add in the remaining 1 3/4 cups of powdered sugar, 3 tablespoons whole milk, 1/2 tablespoon vanilla extract, and 1/8 teaspoon salt. Mix on low until incorporated.
Fudge Icing
- In a double boiler, add in the 2 ounces dark chocolate chips, 2 ounces milk chocolate chips, and 2 tablespoons butter. Stir occasionally until the chocolate is melted.
- Add in the 2 1/4 cups powdered sugar, 1 tablespoon light corn syrup, 1 teaspoon vanilla extract, and 1/8 teaspoon salt. Stir until the chocolate looks like it wants to seize up.
- At this point, take 4 tablespoons hot water from the bottom of the double boiler and add them into the chocolate mixture. Stir until the chocolate thins out. The fudge icing should make thick ribbons. If it’s too thick, add about a tablespoon of additional hot water. If it’s too thin add a small amount of powdered sugar.
- Keep the fudge icing over the double boiler otherwise, it will harden up and will not be spreadable.
Assemble
- After the cookies have cooled, spread the fudge icing on half of the cookie. Do all the fudge sides of the cookies first. By the time you get to the white icing, the fudge will be hard and will make your life a lot easier. I promise.
- After the fudge icing has been applied, spread the white icing on the other half of the cookie.
- Store in an airtight container.
Notes
Nutrition
(Nutrition facts are an estimate and not guaranteed to be accurate. Please see a registered dietitian for special diet advice.)

Oh my, these were amazing! The chocolate icing was to die for . I ran out of time and put the batter in the fridge and made some cookies the next morning and they came out cakier and less like a cookie! I had fans of both which was great!