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Dark Chocolate Cherry Thumbprints


  • ½ c butter, softened but not melted
  • ½ c brown sugar
  • ½ tsp salt
  • 1 tsp vanilla
  • 1 to 2 tbsp milk (so mixture can be easily rolled into balls)
  • 1-½ c Gold Medal flour
  • powdered sugar (to coat cooled cookies)
Chocolate Filling
  • ½ c DARK chocolate chips
  • 1 tbsp shortening
  • 2 tbsp light corn syrup
  • 1 tbsp water
  • 1 tsp cherry juice (from Maraschino cherry jar)
  • 30 maraschino cherries (stems removed and well drained)


  1. In a stand mixer, cream softened butter with the brown sugar. Add salt, vanilla and 1 tbsp milk, and mix until well blended. Add flour and mix until mixture forms coarse crumbs that stick together. (Add additional 1 tbsp milk if needed.)

  2. Using a spoon or a 1-¼" cookie scoop, put dough into palm of hand and roll between palms to form a 1" to 1-¼" ball. Place balls on ungreased cookie sheet.

  3. With thumb, form deep indent in each cookie. Bake at 375° for 10-12 minutes until firm but not brown. Remove cookies from sheet to a cooling rack and cool completely.

  4. When cookies are cool, roll them in powdered sugar to coat thoroughly.

  5. Add filling ingredients (dark chocolate chips, shortening, corn syrup, water, and cherry juice -- NOT maraschino cherries) to a microwave-safe dish. Micro on high for 20 seconds. Stir and micro again another 10 seconds. Mix chocolate until silky smooth. Return to micro 5 seconds at a time if necessary.

  6. Using a pastry bag or small spoon, fill each cookie indent with a mound of melted chocolate. Allow chocolate to set a few minutes, then add well-drained maraschino cherry to top of each cookie. Serve immediately or refrigerate no more than 2 hours.

  7. Make ahead tip: Make cookies and freeze or store in air-tight container until needed. Mix chocolate filling just before serving. Top with cherry and serve.