When it comes to Halloween treats, it’s hard to beat something both cute and delicious. These Milk Chocolate Stuffed Jack‑O’‑Lantern Cookies combine the sweet comfort of brown sugar and spiced cookie dough with a melt‑in‑your‑mouth milk chocolate center—and a little spooky fun with pumpkin‑shaped faces. They’re perfect to bake with kids, serve at a party, or just enjoy with a cozy drink while the autumn wind blows.
What Makes These Cookies Special
- Spiced brown sugar dough — cinnamon, ginger, and nutmeg give warm fall flavor without using pumpkin, so you get a firm but tender cookie.
- Milk chocolate filling — melted milk chocolate sandwiched inside gives a gooey surprise.
- Pumpkin shape + jack‑o’‑lantern face — fun visual appeal for Halloween. And don’t stress about perfection—wobbly faces are part of the charm.
- Cinnamon sugar finish & browned butter — after baking, brushing with browned butter and sprinkling cinnamon sugar adds sparkle and that extra layer of flavor.
Ingredients (for ~30 cookies)
- 3 sticks (1 ½ cups) salted butter, softened
- 1 ¼ cups light brown sugar, packed
- 1 tablespoon pure vanilla extract
- 2 eggs (room temperature)
- 4 ½ cups all‑purpose flour
- 1 teaspoon baking soda
- 1 teaspoon cinnamon
- ½ teaspoon ginger
- ¼ teaspoon nutmeg
- ½ teaspoon salt
- 12 ounces milk chocolate, melted
For the cinnamon sugar coating:
- 2 tablespoons salted butter (for brushing)
- 3 tablespoons cinnamon sugar
Instructions
- Cream & mix dough
In a large bowl, cream together softened butter, brown sugar, and vanilla until light and fluffy (about 3‑5 minutes). Add eggs, one at a time, blending after each. Then add flour, baking soda, cinnamon, ginger, nutmeg, and salt. Mix until a dough forms. - Roll & cut
Generously flour your work surface. Divide dough in half and shape into discs. Roll each disc to about ¼‑inch thickness. Use a pumpkin‑shaped cookie cutter to cut shapes. Transfer cut cookies to a parchment‑lined baking sheet. On half of the cutouts, use a paring knife (or a smaller cutter) to cut out eyes & mouth for jack‑o’ lantern faces. Freeze the cookie sheets (covered) for about 15‑20 minutes to firm dough. - Bake
Preheat oven to 350°F (about 175°C). Bake the cookies (middle rack) for 8‑12 minutes until just lightly golden—just don’t overbake. Let cool on baking sheet for 5 minutes, then transfer to a wire rack to cool completely. - Add finishing touches
Brown some butter in a pot until it smells toasted (2‑3 minutes). Remove from heat and let it cool for about 5 minutes. Brush this butter over the top halves of the pumpkin cookies (the ones with no faces), then sprinkle with cinnamon sugar. - Assemble with chocolate
Spread melted milk chocolate over each “plain top” cookie, then sandwich a face‑cut cookie over it, gently pressing to adhere. You can serve immediately, or let the chocolate set. Store in an airtight container for up to 3 days.
Tips & Variations
- If you don’t have a pumpkin cookie cutter, cut simple round shapes and carve eyes & mouths with a sharp paring knife.
- For softer cookies, bake on the lower end of the time range (8 min); for firmer ones, closer to 12.
- Want to switch up the flavor? White chocolate, dark chocolate, or even a flavored filling like salted caramel or peanut butter could work.
- For extra richness, use browned butter in the dough too.
Prep & Timing
- Prep time: ~30 minutes (includes mixing, rolling, cutting, freezing)
- Cook time: ~15 minutes (baking + finishing touches)
- Total time: ~45 minutes
Serving & Storage
These make about 30 cookies. Great for Halloween parties, gifting, or just satisfying a chocolate craving. Store in an airtight container; if the weather is warm, keeping them refrigerated helps maintain the chocolate filling. They’re best within 3‑4 days.
Why This Recipe Belongs on Your Halloween Menu
There’s something magical about combining cute presentation with decadent flavor. These cookies hit both: the jack‑o’ lantern motif brings festivity; the spices bring nostalgia; the melty chocolate filling offers a delightful surprise. If you want treats that look amazing but are still very doable at home—that’s this recipe.