Jack-O’-Lantern Sandwich Cookies Recipe

I absolutely love how festive and fun this Jack-O’-Lantern Sandwich Cookies Recipe turns out every single time. They’re not only eye-catching with their cute little pumpkin faces but also packed with cozy pumpkin spice flavor that just screams fall. Whether you’re baking for a Halloween party, school event, or just to satisfy that seasonal sweet tooth, these cookies really bring a smile to everyone’s face.

When I first tried this Jack-O’-Lantern Sandwich Cookies Recipe, I was amazed at how easy it was to get those perfectly shaped cookies, thanks to chilling and freezing the dough before baking. Plus, the cream cheese frosting is the perfect balance—rich, tangy, and just sweet enough to complement the pumpkin spice dough. You’ll find that these cookies hold their shape well and taste like fall in every bite!

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Ingredients You’ll Need

The magic of these Jack-O’-Lantern Sandwich Cookies Recipe lies in using simple, wholesome ingredients that bring deep flavors together. You’ll want to pick cold butter and good-quality pumpkin puree to get the most luscious dough.

• All-purpose flour: The foundation for your cookie’s tender yet sturdy texture, perfect for shaping.
• Pumpkin spice: Adds that unmistakable warm fall flavor with cinnamon, nutmeg, and clove.
• Baking powder: Helps cookies rise just enough while keeping them soft.
• Kosher salt: Enhances all the flavors without overpowering the sweetness.
• Butter: Use softened butter for creamy dough that’s easy to work with and rich in flavor.
• Granulated sugar: For sweetness and slight crunch in the cookie’s bite.
• Brown sugar: Adds moisture and complements the pumpkin with its caramel tones.
• Egg: Binds the dough and adds structure.
• Pumpkin puree: The star ingredient for flavor and moisture; be sure it’s pure pumpkin, not pie filling.
• Vanilla extract: Deepens flavor and adds aromatic warmth.
• Cream cheese: Softened to create smooth, tangy frosting that balances the spice perfectly.
• Powdered sugar: Sweetens and thickens the frosting for easy spreading.

Variations

I love experimenting with this Jack-O’-Lantern Sandwich Cookies Recipe for different seasonal vibes or dietary needs. Feel free to switch up the frosting or add mix-ins to make these pumpkins truly your own.

• Frosting Swap: I’ve tried swapping cream cheese frosting for a cinnamon buttercream, which adds a cozy spice that’s delightful for cinnamon lovers.
• Gluten-Free Option: Using a gluten-free all-purpose flour blend works well—just make sure your blend contains xanthan gum for structure.
• Extra Pumpkin Flavor: Adding a teaspoon of pumpkin pie spice instead of just pumpkin spice amps up the warmth, especially for colder nights.
• Mini Cookies: Making smaller cookies is great for kid parties; they also freeze and thaw easily for quick treats.

How to Make Jack-O’-Lantern Sandwich Cookies Recipe

Step 1: Whisk Dry Ingredients Together

Start by mixing your flour, pumpkin spice, baking powder, and salt in a large bowl. This blend makes sure your spices are evenly spread and ensures the leavening agent is distributed so your cookies bake uniformly. I like to whisk these dry ingredients well because it’s easy to miss small spots, which can cause uneven flavor or texture.

Step 2: Cream Butter and Sugars, Then Add Wet Ingredients

Using a hand mixer, beat the softened butter with granulated and brown sugar until creamy and fluffy—this usually takes 3-4 minutes. Then, add the egg and beat that in thoroughly. Next up, add your pumpkin puree and vanilla extract, mixing well until combined. This step locks in all the moisture and flavor. Don’t worry if the dough looks soft at this point; chilling will firm it up.

Step 3: Combine Dry and Wet Ingredients, Chill Dough

Slowly add the dry ingredients to the wet mixture, beating just until combined. Overmixing here can make the cookies tough, so stop once you see there’s no more loose flour. Divide the dough in half, shape into discs, wrap them up, and refrigerate for at least 2 hours (or up to 3 days). Chilling is key—trust me, it helps the dough keep its shape and makes rolling out way less sticky.

Step 4: Roll Out Dough, Cut Pumpkin Shapes

Once chilled, preheat your oven to 350°F and line baking sheets with parchment paper. Lightly flour your work surface and roll out one disc of dough to about ¼ inch thick. Use your pumpkin cookie cutter to cut out the shapes. Place the cut cookies on the baking sheets—you’ll want to save half for the tops of your sandwiches.

Freeze these cut cookies for about 15 minutes—this chilling after cutting helps prevent spreading and keeps those Jack-O’-Lantern faces sharp after baking. Re-roll scraps, but keep in mind extra chilling may be needed.

Step 5: Carve Faces and Bake

This step is my favorite and where the cookies turn from cute pumpkins to spooky Jack-O’-Lanterns! Using a small paring knife, carefully cut out faces in half of the cookies—you can get creative here or stick to classic triangle eyes and jagged smiles. If you notice the dough getting too soft to cut neatly, pop the trays back into the freezer for a few minutes before continuing. Bake the cookies for 8 to 10 minutes until just set but not browned.

Step 6: Prepare the Cream Cheese Frosting

While the cookies cool completely, whip up your cream cheese frosting. Beat the softened cream cheese with powdered sugar until smooth and fluffy. Add vanilla and a small pinch of salt to balance the sweetness. This frosting is what really makes these sandwiches shine, with its smooth, creamy tang matching the pumpkin spice flavors.

Step 7: Assemble Your Jack-O’-Lantern Sandwich Cookies

Once cookies have cooled, flip the solid pumpkin cookies over (the ones without faces) and spread a generous layer of frosting on each. Top with a cookie that has a carved Jack-O’-Lantern face, pressing gently to sandwich together. The cut-out faces let the frosting peek through like glowing pumpkin eyes, which my family absolutely adores!

How to Serve Jack-O’-Lantern Sandwich Cookies Recipe

Garnishes

I usually keep it simple with these cookies, but sometimes I sprinkle a little cinnamon sugar on top before baking for some sparkle. Fresh mint leaves placed nearby add a pop of green that contrasts beautifully with the orange pumpkins for party trays. If you want to get fancy, tiny edible orange and green sprinkles can turn these into show-stoppers!

Side Dishes

These Jack-O’-Lantern Sandwich Cookies are sweet enough to shine alone but pair wonderfully with warm apple cider or a rich hot chocolate when serving at fall gatherings. A small bowl of mixed nuts or roasted pumpkin seeds complements the pumpkin spice flavors perfectly, offering a crunchy contrast.

Creative Ways to Present

For Halloween parties, I’ve displayed these cookies on a tiered dessert stand surrounded by mini gourds and autumn leaves for an instant festive look. I once made a cookie platter shaped like a pumpkin patch using these cookies as the “pumpkins” and green icing “vines,” which was a real crowd-pleaser. Wrapping a few in cellophane with orange ribbon makes sweet little gifts too!

Make Ahead and Storage

Storing Leftovers

I store leftover cookies in an airtight container layered with parchment paper to keep the frosting from sticking. Stored this way, they stay fresh for up to 4 days at room temperature. If your kitchen is warm, pop the container in the fridge to prevent the frosting from melting, but bring cookies back to room temp before eating for best flavor.

Freezing

I’ve frozen the cookies both assembled and just the baked cookie halves before adding frosting. For assembled cookies, wrap individually in plastic wrap and place in a zip-top bag—freeze up to 2 months. Thaw overnight in the fridge and then come to room temp before serving. For better texture, freezing cookie halves separately and frosting fresh after thawing keeps the frosting bright.

Reheating

To enjoy leftovers, I like to let them sit out at room temperature for 30 minutes if refrigerated or thawed from frozen. I generally avoid microwaving because the frosting can get melty and the dough soft, but you can warm a cookie gently in a toaster oven for a few minutes if you prefer a more freshly baked feel.

FAQs

Final Thoughts

This Jack-O’-Lantern Sandwich Cookies Recipe has become one of my fall favorites because it combines fun, flavor, and a little bit of nostalgia all in one bite. I love how easy it is to make these festive treats that look impressive but don’t require a ton of fancy ingredients or special skills. If you’re looking for a seasonal recipe that’s sure to wow the family or friends while filling your kitchen with that wonderful pumpkin-spice aroma, I wholeheartedly recommend giving these a try—you won’t regret it!

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