Date Pinwheel Cookie Recipe

A mid-century pinwheel recipe that makes a simple and irresistible cookie. They’re lightly sweet and soft. The logs freeze well, so make a big batch, and pull a log out when you need a quick, fresh baked treat.

This is a recipe from my Grandma Little, which came to me via my Aunt Dana. It was feared to be a lost recipe, and being a family favorite, nearly a tragedy. Fortunately, it was excavated by my aunt, and now preserved here forever, on the internet. (Assuming the internet is going to be a forever-thing. Maybe we should chisel it in stone, just in case.)

Date Pinwheel Cookie

Yield: 4 large logs, yielding about 1 1/2 dozen cookies each. 
Vintage date pinwheel recipe from my Great Grandma Little. Makes a lightly sweet and soft cookie that has long been a family favorite. 
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Ingredients
  

For Date Filling:

  • 3/4 cup water
  • 3/4 cup sugar
  • 1 1/2 lbs pitted dates, roughly chopped

For Cookie Dough:

  • 1 cup soft butter (2 sticks, 8 ounces)
  • 1 cup light brown sugar
  • 1 cup white sugar
  • 3 eggs, room temperature
  • 1 tsp vanilla extract
  • 1/2 tsp salt
  • 1 tsp baking soda
  • 5 cups all purpose flour

Instructions
 

Make Date Filling:

  • In small pot over medium low heat, heat sugar, water & chopped dates. Let cook until sugar melts and forms a syrup. Use a wooden spoon or potato masher to break up dates more, and make a thick paste.
  • Pull off the heat and cool to room temp.

Make Cookie Dough:

  • In large bowl, or stand mixer with paddle attachment, cream together butter and sugars. 
  • Add eggs, one at a time, mixing thoroughly after each addition. Add vanilla extract.
  • Add dry ingredients, and mix thoroughly. Divide dough into 4 equal portions.

Assemble Pinwheels:

  • Roll out each lump of dough onto parchment, until 1/2″ thick. Use a knife to square up your dough (scraps can be saved and used for to make a mini log, with extra filling).
  • Spread an even layer of date filling on dough, leaving one of the short ends bare to make for easy sealing. Don't use so much filling that it's hard to roll up, but it's also the good stuff, so don't skimp. (I actually recommend using *slightly* more filling than what is in the picture)
  • Tightly roll up your log, rolling toward the end you left bare. Press to seal.  Wrap up in parchment paper, and let chill in fridge for a few hours.
  • Once dough is chilled, preheat oven to 325, and line baking sheets with parchment. Slice logs into 1/2″ thick rounds. Place on prepared sheets, and bake until lightly brown, about 15 minutes.