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 ’50s,) cookies just weren’t what they are today, but these stand the test of time.
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!
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.Print
Grandma’s Old-Fashioned Date Pinwheels
- Total Time: 45 minutes plus chill
- Yield: about 4 dozen 1x
- Category: Desserts
- Cuisine: American
1 pound (2-1/2 cups chopped) dates
1/2 cup sugar
1/2 cup water
1 cup + 2 tablespoons butter, softened (original recipe stated 1 cup shortening)
1 cup granulated sugar
1 cup packed brown sugar
3 eggs, well beaten
1 teaspoon vanilla
4 cups all-purpose flour
1 teaspoon baking powder
1/2 teaspoon soda
1/2 teaspoon cinnamon
1/2 teaspoon salt
1/4 teaspoon ground clove
1/4 teaspoon nutmeg
In a heavy saucepan, cook dates, sugar & butter over low heat at a bare simmer until thick and smooth, about 10 minutes. Cool completely to room temperature and set aside. Note: the filling is difficult to spread when cold.
In a large bowl, cream butter and add white sugar gradually, beating until light and fluffy. Beat in brown sugar, then eggs and vanilla.
Combine the flour, baking soda, baking powder, cinnamon, salt, clove & nutmeg in a bowl. Gradually add to the creamed mixture and mix well. Divide into three portions. (I found it easier to roll if refrigerated until cool.) After cool, roll out each portion of dough on a lightly floured surface into a rectangle, about 1/4 inch thick. (I think mine came to about 12 x 9 inches) Gently spread with date mixture.
Tightly roll up each portion jelly-roll style, starting with a long side; wrap in plastic wrap. Refrigerate until firm, several hours or preferably overnight. For a rounder cookie, after they have chilled for a while but before they are completely hard, remove from the fridge and while still wrapped, roll the dough back and forth to reshape so there is no “flat” side. The dough will keep chilled for several days and may be frozen. If frozen, thaw overnight in the fridge before continuing with the recipe.
When ready to bake, preheat oven to 350 degrees F.
Unwrap and cut into 1/4″ slices. Note: This was according to the original recipe, we found we preferred them a bit thicker, as shown, at about 3/8″ thick) Place an inch apart on baking sheets. (Ideally, use parchment so the warm cookies can be removed from the sheet and don’t become misshapen.
Bake at 350° for 10 – 12 minutes until very lightly browned and edges are set. Cool for several minutes until they begin to firm up, then remove to wire rack to finish cooling. These burn easily, so watch carefully.
Store in an airtight container at room temperature, or freeze for up to 3 months.
Keywords: Cookies, Dates, Desserts, Dried Fruit, Family Recipe, Fruit Desserts, Grandma's Recipe,
I’ll be taking these Cookies to the Fiesta Friday 100 anniversary extravaganza, and I’m also co-hosting this event, so a big shout out to Angie from the Novice Gardener and Fiesta Friday for putting the event on and Steffi from Ginger&Bread, Suzanne from APugintheKitchen and Judi from CookingwithAuntJuju for co-hosting, too. Stop by, say hi, visit and mingle and I hope to “see” you there!
Of course, I’ll also be posting to Throwback Thursday, a link party co-hosted by Moi!! Yes, that’s me, yours truly! And Alli, Quinn & Meaghan – you’ll see all their links on Throwback Thursday!