Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies came down to me from my Grandma, Irene, my Mom’s Mom. Of all the cookies served at Christmas, these were hands down my favorite.

Grandma’s Old-Fashioned Date Pinwheels

I was born in the late 50s, so these have definitely stood the test of time! As a matter of fact, I was heartbroken for years when I couldn’t find the recipe in my Grandma’s recipe box. Well, it turned out Mom had the recipe, but it took years before it came to light. Now it will never be lost!

About Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies:

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 has beautiful, lightly crispy edges.

So altogether, the cookies are soft and chewy with a bit of crisp on the edges and nothing short of a delight. Of course, I couldn’t have vocalized all that as a child – for one, my mouth was probably stuffed with these cookies!

I knew, even then, when a good thing was going on, and I was 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! And when Grandma finally gave me the job of slicing the cookies, I took it very seriously, probably holding my breath with each slice.

Grandma’s Old-Fashioned Date Pinwheels

Making Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies:

So, pinwheel cookies: These are icebox cookies, slice and bake, so plan ahead. They are made in two parts. There’s the date filling, which is cooked and cooled, and then there’s the cookie portion.

The cookie portion is rolled out, the filling spread on top, and then the whole works is rolled up into logs. This is where the icebox portion comes in: the logs are chilled in the fridge, and once cold and firm, sliced and baked.

That makes Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies perfect to have on hand. They can be mixed up and chilled, and pulled out for fresh cookies for an event, or anytime guests drop by.

Helpful Hints:

• Dates are sticky and will stick to your knife when cutting. Spray your knife with cooking spray. If sticky residue does build up, clean off with a warm, wet rag, respray, and continue.
• If the dates aren’t breaking down into a soft, jammy substance as it’s cooked, add about 1/2 teaspoon of baking soda.
• If dates are precut, they may be tossed in Dextrose – cut back on the sugar in the recipe by a tablespoon.
• If the rolls aren’t as round as you wish, the dough was probably warm. Reroll them after they’ve cooled for about an hour.
• To make slicing easier, use dental floss. Simply slide the floss under the roll, pull up, and cross over both ends, and you’ll end up with perfectly sliced cookies.

Make Ahead:

• These Date Cookies must be made ahead; they need chilling time in the fridge before slicing.
• They’ll keep several days in the fridge and can be frozen for several months. If freezing, thaw in the refrigerator.

Leftover Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies:

Store tightly covered at room temperature, but don’t mix with other cookies; the texture can change.

Once baked, they can be frozen, well wrapped, for several weeks. Thaw at room temperature.

Other Cookies You Might Like:

• White Chocolate Cranberry Cookies – while not a classic holiday cookie, this is super festive and another family favorite.
• Monster Cookies – these aren’t only for kids! Include these in your holiday assortment, and they’ll go fast.
• Meringue Cookies – these gorgeous cookies are a little something different and super economical to pull off!

Chocolate Swirl Meringue Cookies

Saving Money on Groceries:

What you pay for groceries depends on not just WHERE you shop, but WHEN. Be strategic and stock up at rock-bottom prices.

• The best sales are before holidays; check out Win at the Grocers. Think beyond the occasion & use the opportunity to stock up at a low for the coming weeks to months.
• If available, take advantage of discount stores like Aldi or Lidl. The pricing at Buyer’s clubs is not always the lowest, but can trump in quality. Be selective when shopping there.

The best way to save money on this or any recipe is to have a well-stocked pantry, fridge, and freezer full of sale-priced items.

General Baking Items:

• Never buy baking items when needed and never pay full price. Instead, stock up during your grocery holiday sales, especially before Easter and the Winter Holidays. Many items are up to half off.
• Discount stores have good pricing on baking items year-round, as does your buyer’s club, although quantities are larger.
• Immediately when arriving home, freeze items containing flour or cornstarch for three days.

Butter: 

• If you have a deep freeze (and you should if you can swing it), there’s no reason to buy butter at full price. It goes on sale often and keeps well.
• While on sale before any holiday, rock-bottom pricing is before the Winter Holidays, and often matched by sales before Easter. Count out the weeks between holidays and buy appropriately.
• Discount stores have great pricing on butter year-round (and sale prices before holidays).

Dates:

• Dates, like most dried fruit, will be at a low from the fall through the end of Christmas week. You’ll find best pricing at markets (Asian, Middle Eastern, etc.) and farm supply stores. Pick the quality that fits your recipe and/or budget.
• If in flimsy packaging, rewrap well or place in a heavy ziploc. If hardened or sugar crystallizes, use in recipes where the dates are cooked. Add a bit of baking soda to facilitate softening.

I hope this recipe for my Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies will serve your family as well as it has ours! Happy Holidays!

Mollie

Grandma’s Old-Fashioned Date Pinwheels

Grandma’s Old-Fashioned Date Pinwheels

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• Author: Irene Elsenbast
• Total Time: 45 minutes plus chill
• Yield: about 4 dozen 1x
• Category: Desserts
• Cuisine: American

Ingredients

Scale 1x2x3x

Date Filling:

• 1 pound (2-1/2 cups chopped) dates
• 1/2 cup sugar
• 1/2 cup water

Cookie Dough:

• 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 cloves
• 1/4 teaspoon nutmeg

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Instructions

Date Filling:

In a heavy saucepan, cook dates, sugar & water 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.

Cookie Dough:

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.

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I’m sharing Grandma’s Old-Fashioned Date Pinwheels Icebox Cookies at Fiesta Friday hosted by Steffi from Ginger&Bread, Suzanne from A Pug in the Kitchen.