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5 from 4 votes

Chocolate Cherry Cookies

Buttery cookies studded with maraschino cherries and mini chocolate chips and topped with a Hershey's kiss.
Prep Time30 mins
Cook Time30 mins
Total Time1 hr
Course: Dessert
Cuisine: American
Servings: 48 cookies
Author: Danielle Howard


  • 1 lb unsalted butter (softened)
  • 2 cups powdered sugar
  • 2 teaspoons vanilla
  • 1/2 teaspoon salt
  • 4 1/2 cups all-purpose flour
  • 12 oz mini semi-sweet chocolate chips (or regular size chocolate chips chopped into smaller pieces)
  • 12 oz maraschino cherries
  • Hershey’s kisses (approximately 48)


  • Preheat the oven to 350 degrees F.
  • Start by draining the maraschino cherries and placing them on paper towels to remove most of the moisture. Then cut them into quarters. I’ve found them easiest to cut using kitchen scissors, but you could also use a knife. Set the cherries aside.
  • Add the butter to a large mixing bowl for a stand mixer and beat over medium speed until smooth.
  • Turn the mixer off, add the powdered sugar, vanilla, and salt, and then start beating on the lowest speed and gradually increase to medium speed to avoid getting powdered sugar everywhere.
  • Gradually add the flour about 1/2 cup at a time, mixing well until blended.
  • Take the bowl off the mixer and add in the chocolate chips and cherries. Mix with your hands (nature’s free source of energy) until the chocolate chips and cherries are incorporated into the dough. The dough will be stiff.
  • Take the dough one heaping tablespoonful at a time and shape into a ball. Place onto a cookie sheet and bake for about 14-16 minutes until very light golden brown (these will not get as dark as chocolate chip cookies).
  • While baking, unwrap all of your Hershey’s kisses. Then as soon as you remove the cookies from the oven, place the kisses into the middle of the dough, pressing down slightly. Allow to cool before moving to a plate or serving container.
  • Repeat for the remaining cookies. The dough can also be made ahead of time and refrigerated, just let it sit out for about 15 minutes before shaping and baking.