As the air turns crisp and leaves begin to swirl, I find myself longing for the warm, comforting flavors of fall. Enter the Milk Chocolate Stuffed Jack-O’-Lantern Cookies—my delightful answer to the sweet cravings that accompany the Halloween season. These charming cookies feature spiced brown sugar dough encasing a gooey chocolate center, perfectly celebrating the cozy vibes of autumn. Not only are they a wonderful way to keep the festive spirit alive, but they’re also straightforward to whip up, making them ideal for those last-minute gatherings or fun baking days with family. The gorgeous pumpkin shape and sprinkle of cinnamon sugar on top only add to their appeal, making them a hit at every table. Curious how to create these seasonal treasures? Keep scrolling! Why Are These Cookies a Must-Make? Irresistible flavors: The spiced brown sugar cookies paired with a decadent milk chocolate filling create a flavor explosion that celebrates the essence of fall. Festive appeal: Their adorable pumpkin shape is sure to impress guests at your Halloween or Thanksgiving gatherings. Quick and easy: With minimal prep time, they fit perfectly into your busy schedule. Customizable: Feel free to substitute dark or white chocolate for a unique twist, or play with different shapes to suit any holiday! These cookies are so scrumptious they’ll have everyone asking for seconds—just like my Brown Butter Chocolate cookies or the classic Banana Bread Chocolate. Enjoy the blend of fun and flavor as you bake! Milk Chocolate Stuffed Jack-O’-Lantern Cookies Ingredients Here’s everything you’ll need to create these delightful seasonal treats! For the Cookie Dough Salted Butter – Provides richness and moisture for the dough; feel free to use unsalted butter instead and adjust the salt. Light Brown Sugar – Adds sweetness with a hint of molasses; granulated sugar can be substituted for a milder flavor. Pure Vanilla Extract – Contributes a deep flavor and aroma; imitation vanilla works in a pinch if you’re out of the real stuff. Eggs – Binds the ingredients and ensures the right structure; substitute with a flax or chia egg for a vegan option. All-Purpose Flour – The main structure of the cookies; a gluten-free blend can work well too. Baking Soda – Provides lift for a lighter cookie; baking powder can be used, but will alter the texture slightly. Cinnamon, Ginger, Nutmeg – Adds warmth and spice; adjust these according to your taste or omit for a milder cookie. Salt – Enhances the overall flavor; you can skip this if using salted butter. For the Chocolate Filling Milk Chocolate – The star filling that makes these cookies sing; swap for dark chocolate for a decadent touch. For the Topping Cinnamon Sugar – A sweet finishing touch that enhances the spices; replace with plain sugar if you prefer. Get ready to bake some true festive magic with these Milk Chocolate Stuffed Jack-O’-Lantern Cookies! Step‑by‑Step Instructions for Milk Chocolate Stuffed Jack-O’-Lantern Cookies. Step 1: Prepare the Dough In a large mixing bowl, cream together 1 cup of softened salted butter, 1 cup of light brown sugar, and 1 teaspoon of pure vanilla extract until the mixture is light and fluffy—about 3-5 minutes. Add in 2 eggs, one at a time, ensuring each is fully incorporated before adding the next. Gradually mix in 3 cups of all-purpose flour, 1 teaspoon of baking soda, and your chosen spices until a cohesive dough forms. Step 2: Shape the Cookies Divide the dough into two equal portions, then flatten each into disks about 1 inch thick. Roll out the dough to approximately 1/4 inch thickness on a floured surface. Use a pumpkin-shaped cookie cutter to cut out cookies, transferring them to parchment-lined baking sheets. Continue this process until all dough is shaped, ensuring a mix of plain cookies and those cut for faces. Step 3: Freeze Cookies for Firmness Cut facial features on half of the cookies to create the jack-o’-lantern effect. Place the baking sheets in the freezer for about 15–20 minutes, allowing the cookies to firm up. This ensures the cookies maintain their shape while baking, resulting in perfectly formed Milk Chocolate Stuffed Jack-O’-Lantern Cookies. Step 4: Bake the Cookies Preheat your oven to 350°F (175°C) while the cookies are chilling in the freezer. Once preheated, bake the cookies for 8-12 minutes, or until they turn lightly golden on the edges. Allow the cookies to cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely. Step 5: Prepare the Chocolate Filling While the cookies are cooling, brown 1/2 cup of milk chocolate in a saucepan over low heat. Stir continuously to melt the chocolate evenly. Let it cool slightly before brushing the melted chocolate over the tops of the cooled cookies. This melted chocolate will be the delightful filling of your Milk Chocolate Stuffed Jack-O’-Lantern Cookies. Step 6: Assemble the Cookies Sprinkle a light layer of cinnamon sugar over the chocolate-coated cookies for that extra pop of flavor. Match the decorated cookies with their counterpart without faces, creating a sandwich effect. Gently press them together to secure the gooey chocolate filling within. Step 7: Serve or Store These charming Milk Chocolate Stuffed Jack-O’-Lantern Cookies can be served immediately for the ultimate treat, or stored in an airtight container for up to 3 days. If you intend to keep them longer, consider freezing the unfilled cookies for future indulgence, bringing the festive spirit to any occasion! Make Ahead Options These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are perfect for meal prep, allowing you to savor festive flavors without the last-minute rush! You can make the cookie dough up to 24 hours in advance; simply prepare and refrigerate it, wrapped tightly to maintain its moisture and prevent drying out. Moreover, the prepared cookie shapes can be frozen for up to 3 months—just freeze them on a baking sheet first, then transfer to a freezer bag. When you’re ready to bake, you can pop the frozen shapes directly into the oven—no need to thaw! Finally, add the chocolate filling and cinnamon sugar once the cookies are baked and cooled for that irresistibly fresh touch. This way, you’ll have a delightful batch of Milk Chocolate Stuffed Jack-O’-Lantern Cookies whenever the craving strikes! How to Store and Freeze Milk Chocolate Stuffed Jack-O’-Lantern Cookies Room Temperature: Keep cookies in an airtight container for up to 3 days to maintain their freshness and softness. Fridge: If you prefer a firmer texture, store them in the refrigerator for up to 5 days, but allow them to come to room temperature before enjoying. Freezer: For longer storage, freeze the unfilled cookies in a single layer, wrapped tightly in plastic wrap, for up to 3 months. Thaw before filling. Reheating: To refresh cookies, pop them in a microwave for a few seconds or warm them in the oven at 350°F (175°C) for about 5 minutes, bringing back that gooey milk chocolate goodness! Milk Chocolate Stuffed Jack-O’-Lantern Cookies Variations Feel free to get creative with these cookies and add your personal touch to them! Dark Chocolate: Swap milk chocolate for dark chocolate for a deeper, richer flavor—perfect for chocolate lovers! With a bolder chocolate taste, these cookies will offer a delightful contrast to the spiced cookie base. White Chocolate: For a sweeter twist, use white chocolate as a filling. drench the outsides with melted white chocolate for an extra touch of decadence. This will also create a beautiful contrast between the pumpkin cookies and the filling. Nutty Goodness: Stir in chopped walnuts or pecans to the dough for a satisfying crunch. The nutty flavor pairs perfectly with the spices and chocolate. It’s an excellent way to add texture while keeping that beloved taste of fall intact. Pumpkin Spice Variation: Enhance the autumn flavor by adding canned pumpkin puree to your dough along with some extra spices. This twist will yield a soft, cake-like texture, making each bite even more indulgent—perfect for the holiday season! Dried Fruits: Consider adding chopped dried cranberries or raisins to the cookie dough. These add a chewy texture and a burst of fruity sweetness. They’re a wonderful compliment to the chocolate filling, ensuring a delightful journey for your taste buds! Cinnamon Sugar Coating: Instead of just sprinkling cinnamon sugar on top, roll the entire cookie in this mixture before baking. This creates a flavorful crust that enhances each bite, bringing the warmth of spices to the entire cookie. Halloween Sprinkles: To truly capture the spirit of Halloween, use festive sprinkles to decorate the cookies. Bright colors will make them pop, turning these delightful treats into eye-catching decorations for your gatherings! Lemon Zest: For a refreshing zing, add a touch of lemon zest to the dough. The tartness cuts through the sweetness and adds a unique flavor dimension to your cookies, brightening up those fall vibes. These ideas can transform your Milk Chocolate Stuffed Jack-O’-Lantern Cookies into various delicious treats that suit any occasion! Whether you’re celebrating Halloween or just looking for a cozy weekend bake, these variations will keep your cookie jar full and your family happy. Ready for more sweet ideas? Check out my Blueberry Buttermilk Pancake casserole for another delightful twist! Tips for the Best Milk Chocolate Stuffed Jack-O’-Lantern Cookies Softened Butter: Ensure your butter is softened to room temperature, but not melted. This is key to achieving the right texture in your cookies. Don’t Overmix: When combining the dough, mix just until the ingredients are incorporated. Overmixing can create tough cookies—nobody wants that! Cookie Shape: Use a well-floured surface when rolling out your dough. This prevents sticking and ensures your pumpkin shapes come out perfectly. Monitor Baking Time: Keep a close eye on your cookies as they bake. For chewy cookies, take them out slightly underbaked; for a crispier edge, let them become lightly golden. Alternate Fillings: Feel free to switch up the filling! Dark or white chocolate works beautifully in these Milk Chocolate Stuffed Jack-O’-Lantern Cookies, providing a fun twist. What to Serve with Milk Chocolate Stuffed Jack-O’-Lantern Cookies Indulging in Milk Chocolate Stuffed Jack-O’-Lantern Cookies is delightful, but pairing them with the right sides can create a truly memorable meal spread. Hot Apple Cider: The warm, spiced flavors of apple cider beautifully complement the cookies’ sweetness, enhancing the cozy autumn atmosphere. Picture gathering around a fire with family, sipping cider and enjoying these treats. Pumpkin Soup: A creamy, spiced pumpkin soup adds a savory contrast to the sweet cookies, balancing your tastebuds perfectly. Stunning as a starter at your Halloween gathering! Cinnamon Sugar Tortilla Chips: These sweet chips are a fun twist to accompany your cookies, offering a delightful crunch alongside the soft, chewy texture. Dip them in melted chocolate for an even more festive treat! Cheese Plate: A selection of sharp cheddar, creamy brie, and a touch of honey can create a balanced mix of sweet and savory. This pairing invites everyone to explore contrasting flavors and textures. Autumn Salad: A fresh salad with mixed greens, candied pecans, and cranberries introduces a burst of color and rich flavors alongside your cookies. It’s a refreshing offset to the sweetness. Milk or Hot Chocolate: For a classic combo, serve these cookies with a glass of cold milk or rich hot chocolate. The creaminess complements the decadent chocolate filling beautifully! Spiced Wine: Mulled wine infused with fall spices pairs wonderfully, bringing warmth and a sophisticated touch to your dessert spread. Perfect for a cozy evening gathering! Chocolate Pudding Parfaits: Layering chocolate pudding with whipped cream and crushed cookies creates a rich and indulgent dessert that complements the festive spirit. Caramel Sauce: A drizzle of warm caramel sauce can elevate your cookie experience, providing that luscious touch of sweetness to each bite. Dipping the cookies is highly encouraged! These delightful combinations will surely enchant guests and turn any occasion into a magical fall celebration! Milk Chocolate Stuffed Jack-O’-Lantern Cookies Recipe FAQs What type of milk chocolate should I use for the filling? For the best flavor and texture, I recommend using high-quality milk chocolate bars or chips that melt smoothly. Avoid baking chocolate, as it may not have the same sweetness and creaminess. If you’re a fan of richer flavors, dark chocolate can also be used for a deeper taste! How should I store the cookies after baking? To keep your Milk Chocolate Stuffed Jack-O’-Lantern Cookies fresh, store them in an airtight container at room temperature for up to 3 days. If you prefer a firmer texture, you can refrigerate them for up to 5 days, but remember to let them come back to room temperature before enjoying! Can I freeze the cookies? Absolutely! To freeze, place the unfilled cookies in a single layer on a baking sheet and freeze until solid. Once firm, wrap each cookie tightly in plastic wrap and store them in a freezer-safe bag or container for up to 3 months. Thaw the cookies before adding the chocolate filling for the ultimate treat! What if my cookie dough is too sticky? If you find your dough is too sticky when rolling it out, don’t fret! Simply sprinkle additional flour onto your work surface and the dough itself as needed. Just be careful not to add too much, as this can affect the cookie’s texture. Additionally, chilling the dough for about 30 minutes can help it firm up for easier handling. Is there a substitute for eggs? Absolutely! If you need an egg substitute for a vegan version, you can use a flax egg. To make one, combine 1 tablespoon of ground flaxseed with 2.5 tablespoons of water. Let it sit for about 5 minutes until it thickens before adding it to your dough. This will help bind the ingredients similarly to traditional eggs! How long will these cookies stay fresh? When stored properly in an airtight container, your Milk Chocolate Stuffed Jack-O’-Lantern Cookies should stay fresh for about 3 days at room temperature. If you freeze them, they’ll be good for about 3 months, maintaining their delightful flavors. Just remember to thaw them before eating for the best taste! Delightful Milk Chocolate Stuffed Jack-O'-Lantern Cookies Try these Milk Chocolate Stuffed Jack-O'-Lantern Cookies for a delightful treat this Halloween season. Print Recipe Pin Recipe Prep Time 30 minutes minsCook Time 10 minutes minsCooling Time 5 minutes minsTotal Time 45 minutes mins Servings: 24 cookiesCourse: DessertCuisine: AmericanCalories: 150 Ingredients Equipment Method Nutrition Notes Ingredients 1x2x3x? For the Cookie Dough1 cup Salted Butter Can use unsalted butter1 cup Light Brown Sugar Granulated sugar can be substituted1 teaspoon Pure Vanilla Extract Imitation vanilla can be used if necessary2 large Eggs Can substitute with flax or chia egg for vegan option3 cups All-Purpose Flour Gluten-free blend can work as well1 teaspoon Baking Soda Baking powder can be used but alters texture1 teaspoon Cinnamon Adjust according to taste1 teaspoon Ginger Adjust according to taste1 teaspoon Nutmeg Adjust according to taste1/2 teaspoon Salt Can skip if using salted butterFor the Chocolate Filling1/2 cup Milk Chocolate Can swap with dark chocolateFor the Toppingto taste Cinnamon Sugar Replace with plain sugar if preferred Equipment Mixing bowlBaking sheetscookie cutterSaucepanwire rack Method Step-by-Step InstructionsPrepare the dough by creaming together butter, brown sugar, and vanilla until light and fluffy. Add eggs one at a time. Gradually mix in flour, baking soda, and spices until a cohesive dough forms.Divide the dough into two equal portions, flatten into disks, and roll out to 1/4 inch thickness. Use a pumpkin-shaped cookie cutter to cut out cookies.Cut facial features on half of the cookies, place on baking sheets, and freeze for 15-20 minutes to firm up.Preheat the oven to 350°F (175°C). Bake the cookies for 8-12 minutes until lightly golden. Cool on the baking sheets for 5 minutes, then transfer to a wire rack.Melt milk chocolate in a saucepan over low heat. Let it cool slightly and brush it over the tops of the cooled cookies.Sprinkle cinnamon sugar over chocolate-coated cookies, match with uncut cookies to create sandwiches, and gently press together.Serve immediately or store in an airtight container for up to 3 days. Nutrition Serving: 1cookieCalories: 150kcalCarbohydrates: 20gProtein: 2gFat: 7gSaturated Fat: 4gPolyunsaturated Fat: 0.5gMonounsaturated Fat: 2gCholesterol: 25mgSodium: 100mgPotassium: 50mgFiber: 1gSugar: 10gVitamin A: 200IUCalcium: 10mgIron: 0.5mg NotesEnsure butter is softened but not melted. Mix just until combined to avoid tough cookies. Monitor baking time for desired texture. Consider using dark or white chocolate for alternative fillings. Tried this recipe?Let us know how it was!
