Christmas Cookies: Date Pinwheels

Of all the cookies I've made this December, these are the first I had the pleasure of making with others. These are a family tradition cookie of Matt--my mom's boyfriend/my own pie mentor--and he makes them every year so it seemed natural to include them in the Christmas Cookie series. This is a recipe from Matt's mom in a draft of his cookbook (right? he's pretty cool) and I'm so grateful to have made these with him so the tradition can live on (and on and on).

These are more substantial than your average cookie and while they are time consuming to make, they keep extremely well in the freezer. Some in the fam actually prefer to eat them by freezer light. 

Matt's Date Pinwheels

Swirly and substantial!


  • 1/2 cup butter
  • 1/2 cup brown sugar
  • 1/2 cup white sugar
  • 1 egg
  • 1/2 teaspoon vanilla
  • 2 cups flour
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 pound dates, pitted and chopped
  • 1/2 cup sugar
  • 1/2 cup water
  • 1/2 cup walnuts, finely chopped

In a large bowl, cream together 1/2 cup butter, 1/2 cup sugar, and sugar 1/2 cup brown sugar. Add the egg and vanilla to the mix and bake well. Sift together your dry flour, baking soda, and salt. Slowly add the dry ingredients to your butter mixture until well combined. Split the dough into two equal pieces, wrap in wax paper, and pop in the fridge for an hour and a half or so.

Meanwhile, it's time to get cracking on the date filling. Pit and chop a pound of dates. This is a bit time consuming and can be a bit dangerous as the dates are quite sticky and small! Matt actually cut his finger whilst chopping the dates because I was goofing off and distracting him. (Whoops.) Dump your chopped dates into a larger saucepan along with 1/2 cup water, 1/2 sugar, and 1/2 cup finely chopped walnuts. Cook until the mixture boils and thickens a bit. Let cool on the stove.

After your dough is sufficiently chilled and your date mixture is no longer boiling, grab one of your dough halves, a rolling pin, and some flour. You're aiming for a dough rectangle as you want your pinwheels to be about the same size and shape. I used a bench scraper to help give me even edges and actually made a handy dandy video to show the rolling out process...

You want your dough about a quarter of an inch thick before you smear it with the date mixture. Then you'll roll it up on the long edge and stick it back in some wax paper (twist the ends like tootsie rolls so it doesn't dry out!) to chill in the fridge for another hour and a half.

After your chill period (a primo time to clean up), preheat your oven to 400 degrees Fahrenheit. Grab a sharp knife and cut your log into slices about a quarter inch each and place on a greased baking sheet. Some of your pinwheels may be a bit crumbly or misshapen, but this is okay! They are still delicious! Bake for 8 minutes. Let cook on a wire rack before serving.