Chocolate Cherry Cookies


This is a fun variation on a thumbprint cookie, using fresh cherries instead of a jam. I whipped this recipe together based on some other cookies I’ve made in the past, because we bought a bunch of fresh cherries from a local farm and wanted to use them.

There are a couple of interesting things to say about this recipe. The first is that you should use sweet cherries, not tart cherries. I’m certainly willing to try it with tart cherries, but they tend to go in other recipes I made so I don’t end up with as many left over. If you don’t have access to fresh cherries, you can use frozen, or maraschino if you must.

The other interesting note is the drizzle. It’s not an icing! I made some homemade sweetened condensed milk — which you can learn how to make here — and infused it with chocolate. The end result is something sort of like a chocolate caramel, but softer, which works really well for holding the cherry in place and adding a bit of texture variety to the cookies.

Don’t worry if the dough looks like a mess, by the way. It is. It’s sticky and tricky but it comes together nicely in the end.

Want to make them for yourself? Here’s the recipe!

Chocolate Cherry Cookies

A chocolate thumbprint cookie using fresh cherries as a centerpiece.
Servings 24 Cookies
Prep Time 15 minutes
Cook Time 12 minutes
Total Time 27 minutes


  • Cherry Pitter
  • Stand Mixer
  • Baking Sheet
  • Parchment Paper
  • Sauce Pan
  • Cooling Rack
  • Rubber Spatula


  • 1 Cup Sugar
  • 1 Stick Butter
  • 1 Egg
  • Tsp Vanilla Extract
  • Cup Flour
  • ½ Cup Cocoa Powder
  • 1 Tsp Baking Powder
  • ¾ Cup Sweet Cherries Halved or Quartered, + extra for topping.
  • ½ Cup Sweetened Condensed Milk See blog post to make your own if necessary.
  • 1 Cup Chocolate Chips


  • Preheat your oven to 350℉. Pit and prep your cherries if necessary. Line your baking sheet with parchment paper.
  • Gently blot some moisture off of your pitted cherries to avoid letting the dough get TOO moist.
  • In your mixer, beat together the butter and sugar until creamy and fluffy.
  • Add in the egg and vanilla and beat to combine.
  • Mix the flour, cocoa powder, and baking powder in a small bowl, then add to the butter mixture. Add in the cherries, and continue to mix until combined. You'll mash the cherries somewhat and it will be difficult to fully combine it all, but it will eventually come together.
  • Divide the dough into small 1.5" balls (about 2 tbsp of dough each) and place them about 2" apart on your baking sheet. They won't spread much but they do spread a little.
  • Indent each cookie with your thumb and add one of the pitted whole cherries.
  • In your sauce pan, over medium heat, combine the chocolate chips and condensed milk. Heat and stir until the chocolate is melted and fully mixed. Drizzle this over your cookies.
  • Bake for 10-12 minutes. When done, allow to mostly cool before serving.
Course: Dessert, Snack
Cuisine: American
Keyword: Cherry, Chocolate, Cookies

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