Quite the Pumpkin Batch

katefox3141

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If you hear a cackling voice floating over the wind this weekend, it’s just me, eager with delight that Halloween is so, so very close. It’s been a few months since I’ve made a batch of cookies, so I approached this week’s bake with a “go big or gourd home” mentality. I knew I wanted to make boozy cookies stuffed with chocolate, so the most logical thing to do was make Jack O’Lantern cookies, naturally. I know, ideas like these, they take guts. Pumpkin guts.

Good thing I like to *carve* out time for my baking every weekend then.

I simply took my peanut butter whisky cookie recipe, swapping the whisky for Baileys because chocolate filling needs a boozy-flavored casing to cover it. Since I do a very detailed step-by-step on that blog post, head over there to get the nitty gritty if you need more help getting your dough put together; otherwise, head down the page for the simplified recipe and instructions. You can also view a quick tutorial on my Instagram about how I put these together. But oh my gourdness are these little cookies delightful to both look at and eat, so I am calling it a win in my big “boooooook!” of spooky baking recipes. The cookies are nice and soft with a hint of Baileys, and that semisweet chocolate filling takes them over the top when you heat them up for 10 seconds in the microwave to make it all melty again. It’s like a softer Orange Milano cookie with double the chocolate filling (and booze). It just doesn’t get any better than that…especially at only 152 calories a boozy, chocolate-stuffed cookie! They’re rather large, so one will definitely tide you over unless your stomach is feeling emptier than a pumpkin that’s been turned into a Jack O’Lantern.

Look at his adorable, fat little face. He’s more a plumpkin than a pumpkin, but it works.
My face when someone tells me to smile more.

Recipe and Instructions

Baileys Jack O'Lantern sugar cookies

  • Servings: 24
  • Difficulty: Intermediate
  • Print

Adult sugar cookies with a chocolate filling

You can definitely use all purpose flour if not gluten free. You can also substitute alcohol with the flavor of your choosing; to make kid-friendly, swap the booze for milk.

Ingredients

    FOR COOKIES
  • 3/4 cup of butter at room temp
  • 1 1/2 cups of Lakanto golden monkfruit sweetener (regular brown sugar also works just fine)
  • 2 large eggs at room temp
  • 3 TBS Baileys flavor of choice (I used their light flavor with 40% less sugar in it)
  • 2 tsp vanilla extract
  • 3 1/3 cups gluten free measure-for-measure flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • Orange gel dye
  • Pumpkin cookie cutter

    • FOR CHOCOLATE FILLING
  • 1/2 bag (4-5 ounces) of Lily’s semisweet chocolate chips, melted (you can use whatever brand you’d like; I prefer these since they are sugar free)

Directions

  1. Mix butter and sugar until light and fluffy.
  2. Add eggs, extract, Baileys, and orange gel dye mixing well.
  3. Add baking soda, baking powder, and 1/3 of the flour, mixing well.
  4. Add remaining flour in 1/3s, mixing well (add more orange dye if you need to).
  5. Roll dough into a large ball, wrap with cling wrap, and place in fridge for 30 minutes.
  6. Once chilled, roll out half of the dough with a rolling pin dusted with flour, or cover the ball with more plastic wrap. Roll to about 1/4″ thickness.
  7. Cut out pumpkins with pumpkin cookie cutter; repeat with remaining dough.
  8. Take HALF of your pumpkins (this recipe made 48 cookies total for me, so I cut out faces on 24 cookies) and cut out desired Jack O’Lantern faces with a pairing knife or X-acto knife.
  9. Place Parchment paper or silicone mats on large baking trays. Put 12 cookies on each tray, placing in the freezer to firm for 10-15 minutes before baking.
  10. Preheat oven to 350 while dough chills.
  11. Bake one sheet of cookies at a time to desired doneness. For softer cookies, bake 8 minutes. For crunchier cookies, bake 10 minutes.
  12. Let cookies cool on the sheet for 5 minutes before removing to a cooling rack to cool completely.
  13. Once all cookies have cooled, melt chocolate chips in a microwave safe bowl. I used 50% power for 1 minute, stirred, and heated again for 30 seconds at 50% power to get things smooth and melty.
  14. Use a small spoon or teaspoon to drop a dollop of melted chocolate onto a plain pumpkin and spread evenly.
  15. Take a Jack O’Lantern face cookie and press it on top of the melted chocolate to adhere; repeat until all cookies have been sandwiched together.
  16. Let all cookies harden for 30 minutes before placing in airtight container to save.
  17. I recommend reheating for 15 seconds in the microwave to get chocolate filling melty again before eating.

Nutrition

Per Serving: 152 calories per cookie
7.5 fat/20 carbs/1.8 protein
Orange you glad you have this easy recipe? Bake your spooky heart out!
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Published by katefox3141

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