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Old Fashioned Date Pinwheels

12 Days of Christmas Cookies

These Old Fashioned Date Pinwheels are soft, chewy cinnamon brown sugar cookies with a pecan date filling! They may be old fashioned but they are absolutely sensational! 

These Old Fashioned Date Pinwheels are soft, chewy cinnamon brown sugar cookies with a pecan date filling! They may be old fashioned but they are absolutely sensational!

These cookies are delicious and I don’t even like dates! The brown sugar cookie dough is something that legends are made out of.

Soft and chewy with a delightful cinnamon brown sugar flavor that harmoniously blends with the dates to produce a sweet, chewy cookie with a subtle pecan date flavor.

That was a lot of words to say “ermagherd so amazing!”

These Old Fashioned Date Pinwheels are soft, chewy cinnamon brown sugar cookies with a pecan date filling! They may be old fashioned but they are absolutely sensational!

Remember my Great-Grandmother RoRo? Remember how she always had each grandchild and great-grandchild’s favorite treats waiting whenever they visited? Pecan tassies were mine and Date Pinwheels were my mother’s.

I couldn’t get my paws on RoRo’s pinwheel recipe but I found this one in my new favorite antique Christmas Cookie book.

 

And they are heaven.

These Old Fashioned Date Pinwheels are soft, chewy cinnamon brown sugar cookies with a pecan date filling! They may be old fashioned but they are absolutely sensational!

These cookies are also nice because you can make the dough and filling when you have time, assemble them and then bake them off as the mood strikes or when unexpected guests turn up.

I don’t have those but I assume some people do.

These Old Fashioned Date Pinwheels are soft, chewy cinnamon brown sugar cookies with a pecan date filling! They may be old fashioned but they are absolutely sensational!

Since presumably you’re still reading; Let’s play a game. It’s called “guess why there are two different sized cookies in the pictures”. I’ll even make it multiple-choice for you.

  1. I’m an overachiever and I thought it would look cool in the photos;
  2. The tiny ones are super cute in real life and I cannot resist miniature things; or
  3. I messed up and rolled one pinwheel on the long side instead of the short side.

Hint, hint. The answer is #3, and you should totally make two different sizes too!

But be warned the tiny ones are beyond addicting. One bite and then you’re reaching for another and then you look over and there aren’t enough left to photograph! Who ate my cookies?!

These Old Fashioned Date Pinwheels are soft, chewy cinnamon brown sugar cookies with a pecan date filling! They may be old fashioned but they are absolutely sensational!

These Old Fashioned Date Pinwheels are for the sixth day of my 12 Days of Christmas Cookies! You won’t want to miss the Cranberry Cinnamon Jam Bars,  Rum Refrigerator Cookies, or Cardamom Walnut Snowballs, Spiced Crinkle CookiesCoconut Peppermint Pretzel Bark!!

Old Fashioned Date Pinwheels

Prep Time: 30 minutes

Cook Time: 30 minutes

These Old Fashioned Date Pinwheels are soft, chewy cinnamon brown sugar cookies with a pecan date filling! They may be old fashioned but they are absolutely sensational!

Ingredients

    For the Cookie Dough:
  • ½ cup butter, room temperature
  • 1 cup firmly packed light brown sugar
  • 1 egg
  • 2 cups all-purpose flour
  • ¼ teaspoon cinnamon
  • ½ teaspoon soda
  • ¼ teaspoon salt
  • For the Date Filling:
  • ¾ cup finely chopped pitted dates
  • ½ cup water
  • 1/3 cup sugar
  • 1/3 cup finely chopped pecans

Instructions

    To Make the Dough:
  1. In a medium bowl whisk together flour, cinnamon, soda and salt.
  2. In the bowl of a stand mixer, cream butter and sugar on medium speed until light and fluffy. Add egg and beat well to combine.
  3. Sift flour mixture into the bowl of the stand mixer and mix on low speed just until combined.
  4. Wrap the dough in plastic wrap. It will help you roll out the dough later if you shape it into a rectangle.
  5. To Make the Date Filing:
  6. In a small saucepan cook dates and water until dates are soft. Add sugar and cook until thickened. Stir in pecans. Cool to lukewarm.
  7. To Assemble & Bake:
  8. Divide the dough into thirds. On a lightly floured surface roll out 1/3 of the dough into a rectangle 7 inches by 11 inches. Cover with 1/3 of the date filling.
  9. Starting with the short end (for larger cookies) or the long edge (for smaller cookies) gently but tightly roll up the dough. Wrap in wax paper and refrigerate until firm (several hours or overnight). Repeat with remaining dough.
  10. When ready to bake preheat oven to 375° (190°C). Cut ¼ inch slices of the roll and place ½ inch apart on a parchment lined baking sheet. They don’t really spread.
  11. Bake 8-10 minutes or until the edges are lightly browned.

Notes:

If you make small cookies, you will get 120 cookies (40 cookies per log); if you make larger cookies you will get about 60 cookies (20 per log)

https://americanheritagecooking.com/2015/12/old-fashioned-date-pinwheels/

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13 Comments

  • Shashi at RunninSrilankan
    December 11, 2015 at 1:22 pm

    2 rolls of cookies – 2 sizes of cookies means only one thing – more to eat! Unlike you, Lindsey, I adore dates and if I got a hold of these, I’m willing to bet you’d have a hard time trying to pry these pinwheels from my hand – eventually you’d give up and I’d be in heaven saying ermagherd so amazing as I ate ’em ALL!!!
    Don’t ya just love daydreaming! 🙂

    Reply
  • David @ Spiced
    December 13, 2015 at 9:27 am

    You had me at cinnamon + brown sugar. I might even ignore the fact that there are dates in here. Does Santa get some cookies this year? 🙂

    Reply
  • Laura @ Laura's Culinary Adventures
    December 15, 2015 at 4:04 pm

    So pretty! I really like dates so I’m sure I’d like these cookies!

    Reply
    • Lindsey
      December 30, 2015 at 11:29 am

      If you like dates and brown sugar then these cookies are your new favorites!

      Reply
  • Gretchen
    December 20, 2015 at 5:45 pm

    I love Date Pinwheels. My problem is that mine turn out oval instead of round.

    Reply
    • Lindsey
      December 21, 2015 at 12:18 pm

      Well as you can see, so did mine! lol.
      There are 2 times when pinwheel cookies (or any log cookies) can become more oval and less round. When you roll it initially, roll it tightly and then wrap tightly in wax paper, make sure that the cookies are round to begin with. The second time is when you cut it. If it isn’t properly chilled, then you’ll get an oval; if your knife isn’t super sharp, then you’ll get an oval; and if you aren’t gentle and loving with the dough, you’ll get an oval. Sigh. But don’t worry there is one trick that you can do if it really bothers you. As you cut the cookies keep turning the pinwheel so that a different side is on the bottom when you cut. This will help keep the cookies round. I obviously didn’t do that! My great-grandmother’s pinwheels were ovals, so I didn’t really think about it!

      Reply
  • Gretchen
    December 22, 2015 at 4:40 pm

    As long as they taste good that’s all that really matters. Thank you for the suggestions.

    Reply
  • Rose
    December 14, 2016 at 11:01 am

    I have come late to my appreciation of the flavor of dates. As my first experiment with dates in a cookie I tried the pinwheel date cookie recipe. I made the batter and rolled up the cookies yesterday let it chill overnight and baked this morning. I rolled the cookie batter the long way so that I had a lot of little delicious bites of pinwheel cookies. This recipe takes some effort to make but well worth it. Thank you for sharing. I has been added to my Christmas cookie list.

    Reply
    • Lindsey
      December 20, 2016 at 8:10 pm

      Hooray Rose!!!! Welcome to the date train! Honestly though, I only like them in these cookies! lol I am happy you liked them! Merry Christmas

      Reply
  • Christian
    December 17, 2017 at 2:11 pm

    I will make these tomorrow, but am planning to add all the christmas spices to them…(anis, cloves, nutmeg, ginger..). It should work….

    Reply
    • Lindsey
      December 26, 2017 at 1:19 pm

      Oh yes, that sounds like it will be delightful! It is a wonderfully spiced brown sugar cookie! Let me know how they turned out!

      Reply
  • Maureen Sandor
    August 10, 2020 at 11:56 am

    I make your Apricot Kolaches- Hungarian Christmas Cookie. I don’t save them for Christmas anymore. My husband and family love them. He wants me to try prune ones, he loves prune in cookies, I am doing that today plus some nut ones too! I enjoy your sight very much. PS….My husband is Hungarian.

    Reply
    • Lindsey
      August 11, 2020 at 12:36 pm

      The highest compliments, Maureen! Happy baking! Good luck with the prune ones!

      Reply

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