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Pinwheel Cookies with Dates

Pinwheel Cookies with Dates


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Just in time for Holiday Cookie Exchange are these take on the classic date pinwheel cookie.MORE+LESS-

Make with

Pillsbury Cookie Dough

1

cup finely chopped walnuts

2

packages Pillsbury™ refrigerated sugar cookie dough

Hide Images

  • 1

    Combine dates, sugar, nuts, and water. Some methods have the nuts added after, my family usually just throws in the nuts at the beginning. I’ve done it both ways, tastes the same.

  • 2

    Bring to a boil, reduce heat and cook slowly until thickened, stirring frequently. Let mixture cool.

  • 3

    Place the cookie dough between two pieces of wax paper.

  • 4

    Roll the cookie dough out using a rolling pin.

  • 5

    Lift the top sheet of wax paper.

  • 6

    Shape the cookie dough with your hands to more of a rectangle shape if too round.

  • 7

    Place filling onto rolled out cookie dough. Spread filling out leaving about 1/2 inch around all the edges.

  • 8

    Using the wax paper as you guide, starting at one of the long ends, slowly roll up the cookie dough in jelly roll form.

  • 9

    Roll the dough all the way up until a log is formed

  • 10

    Roll up dough in waxed paper and seal ends to prevent air from getting in. Place in fridge for at least 4 hours if not overnight. If in a super rush you can place in freezer for 30 minutes.

  • 11

    Using a serrated knife, slice the cookie log about 1/4 of an inch.

  • 12

    Using your hands, reshape the cookies into more round forms.

  • 13

    Place cookies on a greased cookie sheet.

  • 14

    Bake at 375°F for 9-11 minutes and get golden brown around the edges. The filling will stay up and the cookies will sink a little making the spiral very predominate.

No nutrition information available for this recipe

More About This Recipe

  • I turned my nose up at Date Pinwheel Cookies as a kid, but now I love them.

    We had them every year at every Christmas (and only at Christmas) I can remember. They were just a boring cookie with fruit in them ("Ewww", said the 10 year old me). But as I grew, so did my palate.

    Now it’s a different story. If they aren’t on the giant cookie tray I feel like something is missing!

    To make things a little easier on myself this year, I decided to try making them using Pillsbury Sugar Cookie Dough. They do taste different (as the originals use brown sugar) and they look a little different, but I actually like the look. The original cookies are brown on brown; this version makes it easier to see the pinwheel.

    Note: These instructions below are for one roll of cookies, but the recipe is for two rolls. Simply follow the instructions again to make the second roll.

    To make the cookies, begin by gathering dates, sugar, nuts, and water.

    Then combine them. Some versions of this recipe have the nuts added after; my family usually just throws in the nuts at the beginning. I’ve done it both ways and it actually tastes the same.

    Bring to a boil, reduce heat and cook slowly until thickened, stirring frequently. Let mixture cool.

    Place the cookie dough between two pieces of wax paper.

    Roll the cookie dough out using a rolling pin.

    Lift the top sheet of wax paper.

    Shape the cookie dough with your hands to make a rectangle shape.

    Place filling onto rolled out cookie dough.

    Spread filling out evenly, leaving about a 1/2 inch around all the edges.

    Using the wax paper as your guide, start at one of the long ends and slowly roll up the cookie dough in jellyroll form.

    Continue to use the wax paper to roll the cookie dough.

    Roll the dough all the way up until a log is formed.

    Roll up dough in wax paper and seal the ends to prevent air from getting in. Place in fridge for at least four hours, if not overnight. In a super rush? You can place in the freezer for 30 minutes.

    Using a serrated knife, slice the cookie log, making about 1/4 inch-thick slices.

    Using your hands, reshape the cookies into more round forms.

    Place cookies on a greased cookie sheet.

    Bake at 375ºF for 9-11 minutes until they get golden brown around the edges. The filling will stay up and the cookies will sink a little, making the spiral very predominant.

    Add these delicious date pinwheels to your holiday cookie tray and enjoy!


Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies came down to me from my Grandma, Irene, my Mom’s Mom. Of all the cookies we had at Christmas, these were hands down my favorite. Now admittedly way back then (I was born in the 󈧶s,) cookies just weren’t what they are today, but these stand the test of time.

Grandma’s Old-Fashioned Date Pinwheels


Grandma’s Date Pinwheels have so many things going for them. They’re just barely spiced, the perfect amount to complement the filling, which is rich and moist and just a little sticky and in turn, the perfect contrast to the cookie portion of the cookie. And the cookie itself? These pinwheels have beautiful lightly crispy edges but are soft and chewy and the whole cookie is just a delight.

About Grandma’s Old-Fashioned Date Pinwheels:

Now as a kid, I knew all that but I know I couldn’t have vocalized it! For one, my little mouth was probably stuffed full of these cookies….but even as a kid, I knew when there was a good thing going on. I also knew to be in the kitchen at every opportunity. I was always ready to help in any way possible, especially if it meant licking the beaters at the end!

I remember how proud I was when Grandma turned over the job of slicing the pinwheels to me and how hard I tried to slice them perfectly (I was probably biting my bottom lip, a habit I still have when I concentrate on something really difficult.) These days, btw, I slice with them with dental floss.

The funny thing about this recipe is when as a young adult, I asked my Mom for it and she didn’t have it. Several years later, when Grandma passed and I was asked if I wanted anything, all I asked for was her recipe box, hoping to find this and a few other favorites. There was no recipe. It turned out that (as I found out after Mom passed) she had nabbed it from Grandma’s box and it was in hers! So finally after decades, I was able to make these Date Pinwheels again, and as you can tell, this is a highly prized recipe. So this is for the generations passed and those coming up. I hope you enjoy these as much as my family has!

Grandma’s Old-Fashioned Date Pinwheels

Making Grandma’s Old-Fashioned Date Pinwheels:

Now, these are icebox cookies, slice and bake, which means the dough is rolled out, they’re spread with the filling (which maybe, just maybe, I might try increasing a bit next time) then the cookies are rolled into logs. They’re wrapped and chilled then sliced and baked. And as I mentioned above, I like to slice them these days with dental floss. Slide a string of floss under the cookies, lite up each end, wrap around and pull. It helps the cookie keep a round shape and not be compressed by a knife as it slices through.

That means these cookies take a little planning but it also makes it easy to have a roll of cookies in the fridge (you can hold them in the fridge for several days or freeze) at a moment’s notice. That’s great if you want freshly baked cookies on hand if company stops by or you need bake cookies on a busy day or maybe to bring cookies to an evening party. I’m guessing recipes like this are where the big cookie companies got the idea of their rolls of cookies.

I don’t want to forget to mention if you spray your knife lightly with cooking spray, it helps to keep them from sticking still, if it gets too sticky, wipe it clean with a wet, warm cloth. If your dates have been sitting for a while and have hardened a bit and don’t seem to be softening up into a jammy substance as you cook the filling, about 1/2 teaspoon of baking soda will help them break down. If dates are precut, they may be tossed in Dextrose – cut back on the sugar in the recipe by a tablespoon.

The recipe originally called for shortening and shortening does give them an amazing texture. If you use butter, use more. Butter and shortening are not a one to one substitue unless maybe you’re using a high end imported butter. Shortening has more fat per cup than our standard butter so you’ll need a little more butter. I put it in the recipe.

The recipe card didn’t say how many cookies this makes and I forgot to count. I’m thinking it was about four dozen. Next time I’ll make sure to let you know.

Saving Money on Grandma’s Old-Fashioned Date Pinwheels:

The Winter Holidays are an ideal time to save money on groceries, especially baking items. So many items an be picked up an all time low, so it makes sense to buy enough to get through to the next big holiday when these items are going to be on sale again. Here in the states, that’s likely to be Easter.

Dried fruits and nuts are generally at their lowest price of the year right around Thanksgiving to Christmas, although dried dates can be a little pricey they seem to have fallen out of common use in many areas of the country. Check your baking aisle, health food aisle and produce aisle.

Alternative stores like ethic markets, Aldi, health food stores and Farm Supply stores are great places to look for both dried fruits and nuts. If they’re packaged up in zip bags by one of the larger food producers, there is a better possibility you might find coupons and sale prices. If your dried fruit comes in flimsy packaging, repackage them in heavy Ziplocs.


  • ​2 cups, Medjool Dates, pitted
  • 1/3 cup Orange Juice
  • 1 Tablespoon Orange Zest
  • 1 stick Butter, room temp.
  • 4 oz. Cream Cheese, room temp.
  • ½ cup Sugar
  • 1 teaspoon Vanilla
  • 1 extra large Egg Yolk
  • 1 ¾ cup Flour
  • 1 ½ teaspoons Anise Seeds, ground
  • ¼ teaspoon Baking Powder
  • ¼ teaspoon Baking Soda
  • ½ teaspoon Salt​
  • For Topping
  • ½ cup Turbinado or Demerara Sugar
  1. In a food processor blend together dates, juice and zest until creamy. Set aside.
  2. In a large bowl using an electric mixer, beat together butter, cream cheese and sugar until light & fluffy, 3 minutes. Add vanilla and yolk. Blend well scraping sides of the bowl.
  3. In a separate mixing bowl blend the remaining dry ingredients.
  4. Add dry ingredients to butter mixture to fully incorporate.
  5. Divide dough into half. Using rolling pin roll dough into 7” X 9“ rectangles. If dough is sticky roll between wax paper.
  6. Divide date filling between the rectangles. Smooth with a spatula to make an even layer of filling leaving a ¼ inch border around the edges.
  7. Starting with the long side roll up the pinwheels jellyroll style using the wax paper as a guide.
  8. Roll logs in raw sugar to coat completely. Wrap tightly in plastic wrap and chill in freezer or refrigerator until very firm. About 2-4 hours or overnight.

*While Medjool dates are high in natural sugars, they are low on the glycemic index thanks to a balanced amount of soluble fiber. The complex carbohydrates found in Medjool dates are digested at a slower rate, making them a source of dietary fiber and releasing energy to the body over a longer period of time.


Date-Filled Icebox Cookies (Date Pinwheel Cookies)

Icebox……wow! Can you imagine fitting your refrigerated items into the icebox? Especially this time of year?? However, these precious cooks of old adorned their tables with a multitude of candies, cookies and fruitcakes (not so much. ) I do have to wonder how long the chunk of ice lasted.

Oh how times have changed! Some things never change, though. Loving hands made this recipe years and years ago when I was a but little girl. Great-Grandma Hiscocks’ last home was tiny. Her box of toys was a bit larger than a shoe box, and yet I loved visiting her. She always had a cookie for me! (Timer just went off. Gotta check the 1 st batch of these unusual sliced cookies filled with dates and black walnuts.) A few years later my Grandma Ruby, her daughter, trimmed her Christmas table with these little treasures with her loving hands. Then, you know it….my mom never missed a Christmas without making this heirloom favorite, with her loving hands. How I wish I could sit with her and talk about her memories of her mom’s and Grandma’s baking and how it was so different than today, while munching on a pinwheel and washing it down with a cup of hot coffee. (My mom would have tea….as always. She was part English, you know).

Went to a Christmas cookie exchange awhile back and a friend of mine brought pinwheel cookies, too, with of course the same heritage story as mine. I do have to wonder just how far back this recipe goes and how many countries have used it for a favorite staple this time of year. My Grandma Hiscocks’ folks were from Wales. Her husband was from England. You know how those ladies and gentlemen sing about “figgy pudding?” They love their dates and figs in the “old country.” Our trick-or-treating is, in a way, like their Christmas caroling, in that they would carol about the New Born King and expect a piece of fruit or “figgy pudding” for their efforts in the chilling air. (I like their custom much better than ours.)

This recipe…finicky…I might add….has a few steps. (It’s well worth enduring the finickiness (new word). And I hope, with a few tips, you’ll be able to sit down with a loved one and enjoy a cookie or two with your favorite hot beverage. Here we go:


EASY DATE STICKS

This is another easy cookie recipe as an alternative to making the date pinwheel cookies.

  • 17 Ounce roll Pillsbury Slice and Bake Refrigerated Sugar Cookies
  • 1 ½ Cups chopped dates
  • 1/3 Cup sugar
  • ½ Cup water
  • 1 Teaspoon lemon juice

Allow cookie dough to soften at room temperature for 30 minutes.
Combine dates, sugar and water in saucepan over medium heat stirring until mixture thickens.
Remove from heat and stir in lemon juice set aside.
Preheat oven to 350F degrees.
Roll out cookie dough between 2 sheets of wax paper to form a 10 X 12 inch rectangle.
Remove top sheet of wax paper.
Spread dough with date filling in a 4 inch wide strip down center of dough to 1 inch of ends.
Fold shorter sides of dough1 inch over filling.
Bring long sides of dough rectangle over filling overlapping edges pinch edges to seal.
Invert on cookie sheet placing seal side down remove wax paper.
Bake for 25 to 35 minutes until light golden brown cut into slices.


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