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How to Make Delicious Cherry Wink Cookies (With Photo Guide)

I grew up watching and helping my mother make homemade cookies. They were always in our school lunch boxes. Here, I share some family faves.

Homemade cherry wink cookies

Homemade cherry wink cookies

Here we are rapidly approaching the Thanksgiving and Christmas time of year when thoughts of friends and family gatherings as well as food and gift-giving comes to mind.

For several weeks now I have been making and freezing homemade cookies and have now finished the project. They are all safely put up into containers in our large chest freezer and will all be thawed at one time when I am ready to assemble the twelve different kinds that I baked this year and apportion them into decorative cookie tins.

After Christmas last year when the cookie tins that had not previously sold were put on sale, that is when I did some shopping and purchased the tins that I will be giving away this year after filling them with the assorted cookies.

The smaller cookie tins fit nicely into the larger ones so that they did not take up too much space in our hall closet where they were stored. All of them are now washed and dried and, in a short time will be leaving our home filled to the brim with sweet delights.

I think that most people truly appreciate homemade gifts and since the majority of people like cookies they always seem to be gratefully accepted. Since we have been giving them away now for many years some people actually start questioning my husband as to the progress of the cooking baking!

Cut the maraschino cherries into quarters

Cut the maraschino cherries into quarters

Cherry Winks

This cherry wink recipe takes a few extra steps to accomplish but is so pretty and festive when mixed in with more plain-looking cookies that it has been made year after year even though other cookies are sometimes varied.

The topping of that piece of maraschino cherry actually does seem to wink at one! Or is it just my imagination? Wink! Wink!

Ingredients

  • 2 1/2 cups flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 3/4 cup shortening (I use Crisco)
  • 1 cup sugar
  • 2 eggs
  • 2 tablespoons milk
  • 1 teaspoon vanilla
  • 1 cup chopped pecans
  • 1 cup chopped dates
  • 1/3 cup chopped maraschino cherries (plus a quartered cherry for the top of each cookie)
  • 2 1/2 cups cornflakes or more as needed

Instructions

1. Begin by sifting the flour, baking powder, baking soda and salt into a bowl.

Sift the flour, baking soda, baking powder and salt together into a bowl.

Sift the flour, baking soda, baking powder and salt together into a bowl.

Add the eggs to the mixture of shortening and sugar.

Add the eggs to the mixture of shortening and sugar.

2. Combine the shortening and sugar creaming them together.

3. Blend in the eggs and then add the milk and vanilla making sure that all is well mixed after each addition.

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Blend in the sifted flour mixture into the wet cookie mixture.

Blend in the sifted flour mixture into the wet cookie mixture.

Cookie batter prior to adding the nuts, dates and chopped maraschino cherries.

Cookie batter prior to adding the nuts, dates and chopped maraschino cherries.

4. At this point grab your bowl of the sifted dry ingredients and gradually add them to the wet mixture blending well.

5. Finally add the pecans, chopped dates, and the chopped maraschino cherries. (If you do not have pecans, walnuts can be substituted. I actually grabbed the walnuts by mistake this year and it worked out fine according to my hubby who did the honors of tasting them after the cherry winks were baked.)

The cookie batter looks like this after the final addition of the nuts, dates and maraschino cherries.

The cookie batter looks like this after the final addition of the nuts, dates and maraschino cherries.

6. Shape into balls using a rounded teaspoon of dough for each cookie making them about the size of unshelled walnuts. Naturally, you can make them a bit smaller or larger if desired. It is up to you to decide what size cookie you ultimately wish to have.

This batter is quite soft and could probably be chilled, although the recipe does not call for that. I found it is easiest to merely drop the batter by teaspoonful into the slightly crushed cornflakes, and then with one hand they can be rolled in the cornflakes into the semblance of a ball shape prior to placing onto a greased cookie sheet.

Drop a teaspoonful of cookie dough into cornflakes and then roll them into a ball shape.

Drop a teaspoonful of cookie dough into cornflakes and then roll them into a ball shape.

Cherry wink dough rolled in cornflakes and put onto greased cookie sheet.

Cherry wink dough rolled in cornflakes and put onto greased cookie sheet.

7. Top each cookie with a quartered maraschino cherry. Press down slightly so that when the cookie is baked, the cherry will remain on top.

Press a maraschino cherry on top of each cookie prior to baking.

Press a maraschino cherry on top of each cookie prior to baking.

8. Bake in a 375 degree Fahrenheit oven for 10 to 12 minutes. If using a convection oven several sheets of cookies can be baked at one time and oven time will be reduced by a few minutes.

Baked cherry wink cookies fresh out of the oven.

Baked cherry wink cookies fresh out of the oven.

9. Take off of baking sheets and store on wire racks until completely cooled. Do not stack or store until cold.

Yield: Makes about 5 dozen cookies.

Cool the cherry wink cookies on a wire rack.

Cool the cherry wink cookies on a wire rack.

Aren't these cherry wink cookies pretty?

As a part of a cookie assortment, they really add some color and pizzazz to the mixture and besides that, they taste good!

Maybe you already make cookie gifts of your own or will consider making homemade cookies and giving them in the future? Be sure and check out some of my other tested and family-approved cookie recipes. Some of the recipes date back several generations!

Look how pretty these cherry wink cookies look in an assortment readied for gift giving purposes.

Look how pretty these cherry wink cookies look in an assortment readied for gift giving purposes.

Questions & Answers

Question: Can you use parchment paper instead of greasing the cookie sheet?

Answer: Lining a baking sheet with parchment paper is often used in place of spraying the sheet with cooking spray such as Pam, or using some other type of grease. So to answer your question, I would say yes.

© 2011 Peggy Woods

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