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Filled Date Cookies

Filled Date Cookies have a beautiful fruit swirl that invites you back for more!!  Old fashioned date filled cookies are a tradition in my family long before I was born.  

I have been making date filled Christmas cookies for almost half a century.  These beautifully swirled, tender sugar cookies are loaded with a date filling that is incredibly tasty.  

My grandmother’s candy room included these holiday cookies that my dad always requested. You will not find this recipe in any grocery store!!

Filled Date Cookies
Filled Date Cookies

It does not require a cookie cutter but when I make this cookie recipe, it brings a very merry Christmas to several others! Other yummy recipes that you might like are chocolate covered caramels, pecan turtles, and sugar cookies recipe.

A collection of these dessert recipes can be used to make a dessert charcuterie board. This is not a drop cookies recipe and do not refrigerate the cookie if you do not want to. 

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What Are Date Filled Cookies?

Date Pinwheel Cookies are a tender sugar cookie that is swirled with a date and raisin filling, baked to perfection, and full of fruit flavor!  

If you like Fig Newton cookies, then you will like these date pinwheel cookies. My whole family will eat a date cookie or two. 

How to Make the Date Filling

Use a small saucepan and combine the pitted chopped dates, water, raisins, and nuts if desired.  

Tip: Use prepackaged pitted chopped dates to cut down on prep time.  

On a low to medium heat, slowly cook the date filling making sure to stir often to prevent scorching.  Reduce heat if needed.

Cooked Date Filling in a pan.
Date Filling

TIP: Taste test the filling and if it is way to sweet for your liking then add one teaspoon of lemon juice while cooking if desired. When the filling reaches a paste consistency set aside and let cool. 

Gather ingredients to make the date filled cookie dough.  

On medium speed, cream together the softened butter and granulated sugar with an electric mixer or a KitchenAid mixer fitted with a flat paddle.  Make sure to use granulated sugar instead of brown sugar.

Creamed sugar and butter in a mixing bowl.
Creamed sugar and butter in a mixing bowl.

Beat the butter and sugar until the mixture is light and fluffy.  Scrape the sides of the bowl often to properly mix.  

Combine the egg yolks (one at a time) and the vanilla with the cream mixture.   Incorporate together until light and fluffy, making sure to scrape the side of the bowl.  Don’t over beat the creamed ingredients.  

In a large bowl, combine the dry ingredients which includes flour, baking soda, and baking powder.  This recipe calls for a combination of baking soda and baking powder.

Add some of the flour mixture which includes baking soda to the creamed mixture, then the milk, then dry, then milk and finish off with the last of the dry ingredients.  

Blend until all ingredients are combined making sure to scrape the side of the bowl when needed.  

Sugar Cookie Dough in a mixing bowl.
Sugar Cookie Dough in a mixing bowl.

Divide the date cookie dough into 4 equal packages. Chill dough if desired but cookie batter can be used right away.

How to Make Date Pinwheel Cookies

Sprinkle your work surface that you plan to roll the dough out with flour.  Place one of the cookie dough pieces onto the floured surface and sprinkle the dough with flour.  

I like to use a French Style Rolling Pin. With your rolling pin, roll the first package of dough into a rectangle shape about 12 inches by 6 inches.  

Rolled out date cookie dough.

Spread ¼ of the cooled date filling on top of the rolled-out dough.  You want a thin layer of the filling but be careful not to poke holes into the dough when spreading.  

Date filling spread on to cookie dough.
Date filling spread on to cookie dough.

Roll the long side of the dough, starting at one end and work your way to the other side, repeat until you have a full log of the pinwheel dough.  

With a sharp knife, carefully cut 1-inch slices.  The date and raisins might be hard to cut threw, move pieces aside if needed.  

Cut the cookie dough log into 1 inch pieces.
Cut the cookie dough log into 1 inch pieces.

You should get 12 cookie slices per log.  

Place date pinwheel cookies on an ungreased cookie sheet that is lined with parchment paper. Make sure the cookies are spaced out on the baking sheet because they will expand during baking.  If the end comes unsealed, press edges back together.

Sheet pan of filled date cookies.
Sheet pan of filled date cookies.

Repeat this “How to Make Date Pinwheel Cookie” process to make three more date and raisin cookie logs. Making this recipe is a little time consuming but well worth the effort!

How to Bake Pinwheel Cookies with Dates

Preheat the oven to 325°F.  In the preheated oven, place the cookie sheet of pinwheel cookies in the oven and bake for 10 – 14 minutes.  

Cool completely, the date filled cookies, by leaving in the cookie sheets. If desired, place the fully cooked cookie recipe onto a cooling rack.

Baking times will vary so check the baking sheet of cookies often to prevent burning.  The date cookies should be lightly browned on the bottom.  

Store the baked Christmas pinwheel cookies in an airtight container at room temperature for up to 7 days.  

Date Filled Cookies on a tray.
Date Filled Cookies

Filled Date Cookies – FAQ

Can I Freeze Date Cookies?

These Christmas pinwheel cookies freeze well.  Place the baked Christmas cookies in an airtight container with plastic wrap, wax paper, or parchment paper between the layers.  Freeze for up to 2 months.  

What is Date Fruit?

Dried Dates are sun-kissed pieces of fruit that I love to use when baking.  I love dates and will eat then as I am baking with them. To learn more about date fruit, check out Mary’s “What is Date Fruit?” from Delighted Cooking.

What Are Dates Good For?

Dates make a great snack food but are commonly used for baking.  Dates are made into sweet and savory items such as cookies, breads, vinegar, juice, and many other things.  Pitted dates are often stuffed with an assortment of different fillings and served as an appetizer. Did I mention, that I love dates!!

Filled Date Cookies Recipe

Get the full recipe and the nutrition facts by clicking the picture below. 

Yield: 48 Cookies

Date and Raisin Cookie

Filled Date Cookies

Filled Date Cookies have a beautiful fruit swirl that invites you back for more!! Old fashioned date filled cookies are a tradition in my family long before I was born. These beautifully swirled, tender sugar cookies are loaded with a date filling that is incredibly tasty.

Prep Time 30 minutes
Assembly Time 15 minutes
Bake Time 14 minutes
Total Time 59 minutes

Ingredients

  • Date Filling
  • Dates, Pitted, Chopped 2 cup
  • Raisins 1/2 cup
  • Water 1 1/2 cup
  • Walnuts, Chopped (optional). 1/2 cup
  • Cookie Dough
  • Butter, Softened 1 cup
  • Sugar, Granulated 1 cup
  • Egg Yolk 3 yolks
  • Vanilla 1 1/2 teaspoon
  • Flour, All Purpose 3 1/2 cups
  • Baking Soda 1/4 teaspoon
  • Baking Powder 1 teaspoon
  • Milk 1/2 cup

Instructions

  1. How to Make Date Filling Use a small saucepan and combine the chopped pitted dates, water, raisins, and walnuts nuts (optional). On a low heat, cook the date filling making sure to stir often to prevent it from burning. The dried date recipe filling should be a paste consistency, set aside, and let cool.
  2. Make the Pinwheel Cookie Dough Gather ingredients to make the date pinwheel cookie dough.
  3. Cream the softened butter and granulated sugar with a hand mixer or a KitchenAid mixer fitted with a flat paddle.
  4. Mix until it is fluffy and light. Make sure to scrape the side of the bowl.
  5. Blend the egg yolks (one at a time) and the vanilla with the cream mixture. Incorporate together until fluffy, making sure to scrape the side of the bowl. Do not over mix the ingredients.
  6. In a large bowl, combine the dry ingredients together.
  7. Alternating, add 1/3rd of the dry ingredient, then the 1/2 the milk, then 1/3rd dry, then the rest of the milk and finish off with the last of the dry ingredients.
  8. Blend until all ingredients are incorporated making sure to scrape the side of the bowl when needed. Divide the dough into 4 equal packages.
  9. How to Make the Filled Date Cookies Sprinkle the surface with flour. Place the dough onto the floured surface and dust with flour.
  10. Roll the first package of cookie dough into a rectangle shape about 12 inches by 6 inches.
  11. Spread ¼ of the cooled date filling on top of the rolled-out dough. You want a thin layer of the filling.
  12. Roll the 12-inch side of the dough, starting at one end and work your way to the other end, repeat until you have a log of the date cookie dough.
  13. Use a sharp knife, carefully cut 1-inch slices. The raisin cookie filling might be hard to cut threw, move pieces aside if needed.
  14. You should get 12 pinwheel cookies with dates per log.
  15. On a parchment lined baking sheet, place the cookies, making sure the pinwheel cookies are spaced out because they will expand during baking.
  16. Repeat this roll out process to make three more logs.
  17. How to Bake the Filled Date Cookie Recipe Preheat the oven to 325°F. When the oven comes to temperature, place the pinwheel cookies in the oven and bake for 10 – 14 minutes. Baking times will vary so check the cookies often to prevent burning.
  18. The Christmas pinwheel cookies should be golden brown on the bottom.
  19. Store the baked pinwheel Christmas cookies in an airtight container for up to 7 days.

Notes

  • Freeze the cookies for up to 2 months.
  • Chill the cookie dough if desired but not necessary.

Recommended Products

As an Amazon Associate, I earn from qualifying purchases. This page contains affiliate links. Click on the highlighted text in a post to explore a product. If you purchase through one of them, I will receive a commission (at no additional cost to you). I ONLY EVER ENDORSE PRODUCTS THAT I TRULY LOVE. Thank you for your support!

Nutrition Information

Yield

48

Serving Size

1

Amount Per Serving Calories 123Total Fat 5gSaturated Fat 3gTrans Fat 0gUnsaturated Fat 2gCholesterol 26mgSodium 52mgCarbohydrates 18gFiber 1gSugar 10gProtein 2g

Note: For exact nutritional information, consult your dietitian. All nutritional information is simply a guideline.

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If you enjoy this recipe, you may enjoy the following: Cranberry Pinwheel recipe and Old-Fashioned Date Cookies

Cranberry Pinwheel Cookies on a wooden board.
Cranberry Pinwheel Cookies
Old Fashioned Date Cookies with a glass of milk.
Old Fashioned Date Cookies
By on November 27th, 2021
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About Sherry

Welcome to FROM MICHIGAN TO THE TABLE! My name is Chef Sherry Ronning and I am a food blogger from Michigan. Professionally cooking and baking Midwestern Cuisine for more than 30 years. Specializing in fresh fish, venison, farm raised meats and griddle recipes. Please enjoy my recipes!!

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