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Grandmother’s Pinwheel Cookies

Posted May 24 2009 11:26pm

Every month, Jenna over at That Wife hosts a “food challenge”.  This month, in honor of Mother's Day, the challenge was to retrieve our favorite recipe made by our mother and replicate it.  Well, Jenna, I’m bending all sorts of rules here, but once you hear the story behind these cookies, I hope you’ll forgive me.

First off, these are not my mother’s cookies – these are my grandmother’s cookies.  And secondly, I made them not in May, but in December, and the pictures have been sitting on my computer ever since, waiting to be posted (though this challenge did give me the perfect excuse to write up the recipe).  But, December was the first time I ever made the cookies, so I felt like it still qualified in the whole tackling a new recipe; I just did it a bit early.

Up until three years ago, my grandparents always lived a state away from my parents, so “going to Grandma’s house” was always an adventure.  We didn’t have the luxury of just meeting up for dinner; rather, with the four hour drive involved, it was limited to weeks in the summer and long weekends during the school year.  Despite being fortunate enough to have  well-traveled childhood, my favorite place in the world to visit always remained my grandparents’ home; even though it was not exotic, I always knew I would have a wonderful time.  And one thing was always constant throughout these visits – we would park in the driveway, walk in through the basement (oh, how I loved the musty basement smell! To this day, musty basements immediately bring me back to my grandparents’ grey painted basement with the pool table), ascend the curving staircase, and emerge into their black-and-white kitchen with the strawberry border, where my grandmother would be standing with a tray of pinwheel cookies.  Every time.

Fast forward many, many years to December 2008.  Nobody else in my family had ever made the pinwheel cookies, but my grandmother had recently handed down the recipe to me, as her failing health prevented her from doing any more baking.  I had a strange urge to try them for the holidays, so I decided to give it a shot, following her directions and hoping for the best.  Little did I know that the pinwheel cookies would wind up being the comfort food of my family.

Two days after making them, I received a phone call that my grandmother had a massive stroke and was in the hospital.  After finishing his clinical requirements and starting his winter vacation, Husband and I rushed home to join the rest of my already-assembled family, awaiting future news in my parents’ home.  Being the holiday season, everyone was well over their cookie quota, but not knowing what else to do, my Jewish mother continued to try to offer more sweets and desserts to everyone, which were immediately refused.  Observing the scene – everyone so worried – I knew the cookies would take the focus off the not knowing, and instead onto discussing happier memories while we awaited more news the next day.  I emerged from the kitchen with a cookie tin, and everyone groaned.  “No more cookies!”, they protested.  But then, I cracked the lid, and my uncle caught a glimpse inside.  Even he, only married into the family for 12 years, recognized them immediately, and let out a little squeal of delight.  Within 10 minutes, the entire batch of cookies had been devoured, while everyone swapped their favorite stories about my grandmother.  My job was done, and these cookies will ALWAYS hold a special place in my heart as a reminder of my grandmother, and the culinary glue that brings my family together.


Disgruntled Julie’s Grandmother’s Pinwheel Cookies


  • 3 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1 cup unsalted butter, softened
  • 1 1/3 cups sugar
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 2 ounces unsweetened chocolate, finely chopped


  1. In a large bowl, sift together flour, baking powder, and salt.
  2. Beat butter until fluffy, about 3 minutes.  Add sugar and beat until light and fluffy, about 2 minutes more.  Add eggs, one at a time, beating after each addition, then beat in vanilla.  Add flour and beat on low just until combined.
  3. Divide dough in half.  Form 1 half into 4- by 4-inch square, wrap in plastic wrap, and set aside.  Return other half to mixer.  In metal bowl set over pan of barely simmering water, melt chocolate, stirring until smooth.  Add melted chocolate to dough in mixer and beat just until combined.  Form chocolate dough into 4- by 4-inch square and wrap in plastic wrap.  Refrigerate both squares of dough for 30 minutes.
  4. Line large baking sheet with parchment paper.  Cut each dough square into 4 strips.  Roll out one strip of vanilla dough into 6- by 7- inch rectangle (refrigerate all other dough strips).  Remove 1 strip of chocolate dough from refrigerator and, between 2 sheets of parchment paper, roll out into 6-inch by 6-inch square.  Peel off top sheet of parchment from each dough and flip vanilla dough over onto chocolate.  Trim excess chocolate dough to fit size of vanilla dough.  Run rolling pin lightly over doughs to adhere, then peel off top sheet of parchment.  Using parchment as an aid, tightly roll up dough into log.  Wrap in plastic wrap and refrigerate.  Repeat with remaining strips of dough to form 4 logs.
  5. Refrigerate logs 1 hour, then remove from refrigerator and roll each log on counter several times to prevent bottom from flattening.  Refrigerate 3 hours more, then transfer to freezer to store.
  6. Keep dough frozen until ready to slice and bake.  Preheat oven to 350F and grease two large baking sheets.
  7. Using a sharp knife, slice dough into 1/4-inch thick slices and plaice 1 1/2 inches apart on baking sheet.  Bake until vanilla dough is slightly golden, 9 to 11 minutes.
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