Easy Milk Chocolate Stuffed Jack-O-Lantern Cookies

These Milk Chocolate Stuffed Jack-O-Lantern Cookies appeared in my kitchen one chilly October afternoon. I wanted something festive, something that made my grandkids squeal.

The crisp edges and hidden chocolate center felt like the perfect Halloween surprise. Each bite brings that sweet rush paired with buttery cookie layers.

Now they sit on my counter every October, waiting for eager little hands. These cookies became our October tradition without me even planning it.

Why this Milk Chocolate Stuffed Jack-O-Lantern Cookies always gets requests family

I love how the chocolate melts just enough inside without leaking everywhere. It holds its shape while staying soft, and that makes all the difference.

You get that festive pumpkin shape with barely any effort at all. The orange dough looks bright and cheerful on any dessert table.

Kids go wild for the hidden chocolate, and adults appreciate the simple butter cookie base. These Milk Chocolate Stuffed Jack-O-Lantern Cookies somehow please everyone at once.

What you will need to make this Jack-O-Lantern Cookies

• 3¼ cups all-purpose flour plus extra for rolling – I use unbleached when I have it
• 1 teaspoon baking powder – gives a little lift without puffing too much
• ½ teaspoon salt – balances the sweetness nicely
• 1 cup unsalted butter (softened, about 2 sticks) – European style works beautifully here
• 1 cup granulated sugar – standard white sugar is perfect
• 2 large eggs – room temperature blends easier
• 1 teaspoon vanilla extract – pure extract tastes better than imitation
• 12 ounces milk chocolate – I chop bars or use quality chips
• Orange gel food coloring – gel gives vibrant color without thinning dough
• Black gel food coloring – for drawing jack-o-lantern faces
• ½ cup powdered sugar – optional dusting at the end

If you can’t find orange gel coloring, liquid works but add it slowly. The dough might get sticky, so chill it longer if needed.

I once used dark chocolate instead of milk chocolate, and my nephew complained it was too bitter. Stick with milk chocolate for that crowd-pleasing sweetness.

For a fun twist, try adding a pinch of cinnamon to the dough. It gives these cookies a subtle warm spice that feels very autumn.

How I Make This Milk Chocolate Stuffed Jack-O-Lantern Cookies

1. Whisk your flour, baking powder, and salt together in a medium bowl. Set this aside while you work on the butter mixture.
2. Cream the softened butter and sugar in a large bowl for about 4 minutes. You want it pale and fluffy, almost like frosting.
3. Add your eggs one at a time, beating well after each addition. Then stir in the vanilla extract until everything smells wonderful.
4. Gradually fold the dry ingredients into the wet mixture. Mix just until the dough comes together without any dry streaks remaining.
5. Divide your dough in half. Add orange gel coloring to one half, kneading until the color spreads evenly throughout. Irresistible Strawberry Thumbprint Cookies use a similar technique for colored dough if you want more practice.
6. Wrap both dough portions in plastic wrap and chill for at least 35 minutes. I sometimes leave mine for an hour when I get distracted.
7. Preheat your oven to 375°F and line two baking sheets with parchment paper. This prevents sticking and makes cleanup easier later.
8. Roll out the orange dough on a floured surface to about ¼ inch thickness. Use a pumpkin-shaped cutter to cut as many shapes as possible.
9. Repeat the rolling process with your plain dough. You need equal numbers of orange and plain cookies for the sandwiching step.
10. Place half your orange cookies on the prepared baking sheets. Add about a tablespoon of chopped chocolate to the center of each cookie.
11. Top each chocolate pile with a plain cookie, pressing the edges gently to seal. The chocolate stays hidden inside during baking.
12. Bake for 9 to 11 minutes at 375°F until the edges turn golden. The centers will still look soft, and that’s exactly right.
13. Let them rest on the baking sheets for 5 minutes before moving them. This helps them firm up without breaking apart.
14. Transfer to a wire rack and let them cool completely. Once cooled, use black gel coloring to draw jack-o-lantern faces on the orange side.
15. Dust with powdered sugar if you like that snowy effect. I skip this step half the time because they look great either way.

My secrets for getting this Milk Chocolate Stuffed Jack-O-Lantern Cookies just right

Chill your dough properly or the shapes will spread in the oven. I learned this after my first batch turned into orange blobs instead of pumpkins.

Press the edges firmly when sealing the two cookies together. Any gaps let chocolate leak out, and you lose that surprise center.

Use a toothpick dipped in black gel coloring for fine details. You can draw eyes, noses, and mouths with much better control than squeezing from a bottle.

How this Milk Chocolate Stuffed Jack-O-Lantern Cookies fits into my weekly meals

I bake these on weekend afternoons when the house feels quiet. The smell fills every room and brings everyone downstairs asking what’s cooking.

They work for Halloween parties, school treats, or just because October arrived. Sometimes I make them in early November because nobody said pumpkins have a deadline.

Pair them with hot apple cider or warm milk for an afternoon treat. The Best Cranberry Cornmeal Linzer Cookies make a nice companion if you’re filling a cookie platter for guests.

The Best Milk Chocolate Stuffed Jack-O-Lantern Cookies

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• Author: Amelia Bryan
• Total Time: 35 minutes
• Yield: 22 cookies

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Description

Festive pumpkin-shaped cookies with a hidden chocolate center, perfect for Halloween celebrations and autumn gatherings.

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Ingredients

• 3¼ cups all-purpose flour, plus more for dusting
• 1 teaspoon baking powder
• ½ teaspoon salt
• 1 cup (2 sticks) unsalted butter, softened
• 1 cup granulated sugar
• 2 large eggs
• 1 teaspoon vanilla extract
• 12 ounces milk chocolate, chopped or chips
• Orange gel food coloring, as needed
• Black gel food coloring, for decorating
• ½ cup powdered sugar, for dusting (optional)

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Instructions

1. Whisk together flour, baking powder, and salt in a medium bowl. Set aside.
2. Cream butter and sugar in a large bowl for about 4 minutes until pale and fluffy.
3. Beat in eggs one at a time, then add vanilla extract.
4. Gradually fold dry ingredients into wet ingredients, mixing until just combined.
5. Divide dough in half. Knead orange gel coloring into one half until evenly distributed.
6. Wrap both portions in plastic wrap and refrigerate for at least 35 minutes.
7. Preheat oven to 375°F. Line baking sheets with parchment paper.
8. Roll orange dough on a floured surface to ¼ inch thickness. Cut out pumpkin shapes.
9. Roll plain dough to the same thickness and cut out equal number of shapes.
10. Place half the orange cookies on baking sheets. Add about 1 tablespoon chopped chocolate to each center.
11. Top with plain cookies and press edges to seal completely.
12. Bake 9 to 11 minutes until edges are golden. Centers will look slightly soft.
13. Cool on baking sheets for 5 minutes, then transfer to wire racks.
14. Once completely cooled, use black gel coloring to draw jack-o-lantern faces.
15. Dust with powdered sugar if desired.

Notes

Use finely chopped chocolate or quality chips for the filling. Make sure dough is well chilled so cookies hold their shape during baking. Press edges firmly when sealing to prevent chocolate from leaking out.

• Prep Time: 25 minutes
• Cook Time: 10 minutes

Can I freeze these cookies before baking them?

You can freeze the unbaked sandwiched cookies on a tray, then store them in a freezer bag. Bake them straight from frozen, adding 2 extra minutes to the baking time.

Looking for more cozy baking inspiration? Follow me on Pinterest where I share all my favorite seasonal treats and holiday baking ideas.

What if my chocolate leaks out during baking?

Your seal probably wasn’t tight enough around the edges. Press firmly next time, and don’t overfill with chocolate pieces.

How long do these cookies stay fresh?

They last about 5 days in an airtight container at room temperature. The chocolate stays soft, and the cookies keep their texture nicely.

Can I use white chocolate instead of milk chocolate?

White chocolate works fine if that’s your preference. I personally think milk chocolate pairs better with the butter cookie base though.