Jack-O’-Lantern Sandwich Cookies Recipe

If you’re looking for a festive treat to wow your friends and family this Halloween, I’ve got just the thing for you! I absolutely love this Jack-O’-Lantern Sandwich Cookies Recipe because it combines soft pumpkin-spiced cookies with creamy, dreamy cream cheese frosting — all shaped like adorable little jack-o’-lanterns. When I first tried it, I was hooked, especially seeing my kids’ faces light up when they got to pick their favorite pumpkin “face.” Stick with me here, and I’ll walk you through every step so your cookies turn out just perfect.

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Ingredients You’ll Need

Each ingredient in this Jack-O’-Lantern Sandwich Cookies Recipe works together to create that perfect balance between soft spiced cookie and smooth frosting. Here’s what I like to use and why:

• All-purpose flour: The base of the cookies, providing just enough structure without making them hard.
• Pumpkin spice: A blend of cinnamon, nutmeg, and cloves that brings in that warm fall feeling.
• Baking powder: Helps the cookies rise slightly, keeping them soft and tender.
• Kosher salt: Balances the sweetness and enhances all the flavors.
• Butter: Always go for unsalted, softened butter for creamy texture and control over saltiness.
• Granulated sugar: Adds sweetness and a nice crumb texture.
• Brown sugar: Adds moisture and a lovely deeper caramel flavor.
• Large egg: Binds the dough together and gives richness.
• Pumpkin puree: The real star, making these cookies soft and subtly pumpkin-flavored – make sure it’s plain pumpkin, not pie filling!
• Vanilla extract: Adds that background richness and balance.
• Cream cheese: For the frosting, softened for easy mixing and that signature tangy creaminess.
• Powdered sugar: Sweetens and thickens the frosting to spreadable perfection.

Variations

I love playing around with this recipe depending on who I’m baking for or the occasion. Feel free to make it your own – that’s part of the fun, right?

• Gluten-Free Version: I once swapped the all-purpose flour for a gluten-free blend with great success — just make sure it’s a one-to-one replacement mix for baking.
• Orange-tinted Cookies: Adding a few drops of orange food coloring to the dough really amps up the pumpkin look! It’s a kid-pleaser for sure.
• Frosting Flavors: Try adding a little maple syrup or cinnamon to the cream cheese frosting for a subtle twist that keeps it interesting.
• Spooky Shapes: If you don’t have a pumpkin cutter, any Halloween-themed cookie cutters work great — bats, ghosts, or even simple circles!

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

Step 1: Mix the Dry Ingredients

In a large bowl, whisk together the flour, pumpkin spice, baking powder, and salt. This is an important step because it helps distribute everything evenly, so your cookies get consistent flavor and texture. I like to use a sifter or a fine-mesh sieve if I want to be extra sure there are no lumps — it makes rolling out the dough much easier later on.

Step 2: Cream the Butter and Sugars

In another bowl, use a hand mixer to beat the butter with both sugars until it’s light and creamy—this usually takes about 2-3 minutes. I learned this trick the hard way: if you don’t cream enough, your cookies may turn out dense. Then add the egg and beat until just combined, followed by the pumpkin puree and vanilla. These liquids add moisture and richness.

Step 3: Combine Wet and Dry Ingredients

Gradually add the dry ingredients to your wet mix, beating on low speed until just combined. Overmixing here can make the cookies tough, so once you see no streaks of flour, stop! Divide the dough into two discs, wrap in plastic wrap, and chill in the fridge for at least 2 hours or up to 3 days. This rest time is key to firm up the dough so it rolls smoothly and keeps your shapes sharp.

Step 4: Roll and Cut Your Cookies

Line two baking sheets with parchment paper. Take one dough disc at a time and roll it out on a lightly floured surface to about ¼ inch thick. I find a floured rolling pin helps a ton to prevent sticking. Use a pumpkin-shaped cookie cutter to cut out as many cookies as you can, and place them on the baking sheets. Don’t toss those scraps! Just re-roll and cut again. Here’s a great trick: freeze the cookies on the sheets for about 15 minutes to help them hold their shape.

Step 5: Carve the Faces

Preheat your oven to 350°F. Now, use a small paring knife to carefully cut out jack-o’-lantern faces on half of the cookies. If the dough warms up and gets too soft, pop the trays back in the freezer for a bit. This step takes a little patience, but trust me — it’s worth it to get those perfect spooky smiles!

Step 6: Bake and Cool

Bake the cookies for 8 to 10 minutes until they are set but not browned. I watch closely toward the end — you want firm edges but still soft centers. Let them cool completely on the sheets before frosting; otherwise, the cookies can break or the frosting will melt.

Step 7: Make the Cream Cheese Frosting

While the cookies cool, beat the softened cream cheese and powdered sugar in a large bowl with a hand mixer until smooth and fluffy. Then add the vanilla and a pinch of salt to brighten the flavors. This frosting is rich but light, the perfect balance with the pumpkin cookies.

Step 8: Assemble Your Sandwich Cookies

Flip the plain cookies over and spread a generous dollop of frosting on the underside. Top each with a cookie that has a carved face, pressing lightly to sandwich them together. Here’s a quick tip: use a piping bag or zip-top bag with a corner snipped if you want neater frosting layers!

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

Garnishes

I love sprinkling a tiny bit of cinnamon or edible glitter on the frosting to make these cookies pop on the plate, especially for parties. Sometimes I even press a small mint leaf or a tiny chocolate chip “stem” onto the pumpkin’s top for extra cuteness. It’s a simple touch that makes the presentation stand out.

Side Dishes

These cookies pair wonderfully with a warm spiced cider or a creamy pumpkin latte. For a party, I also set out bowls of mixed nuts, caramel apples, or even a small cheese plate to balance the sweetness.

Creative Ways to Present

For Halloween gatherings, I’ve served these cookies stacked in tall glass jars decorated with orange ribbons. You could also set them out on a black platter with some autumn leaves and mini pumpkins to elevate the spooky vibe. Kids love it when each cookie’s face is different, so I sometimes let them help carve the faces before baking—that’s always a huge hit!

Make Ahead and Storage

Storing Leftovers

Once assembled, store leftover sandwich cookies in an airtight container in the fridge for up to 4 days. I like to layer them between sheets of parchment paper to keep the frosting from sticking or smudging the pumpkin faces.

Freezing

I’ve frozen both the baked cookies (before frosting) and the fully assembled sandwich cookies. For best results, freeze the unassembled cookies in a single layer on a baking sheet, then transfer to a freezer bag. They keep well up to 3 months. The frosting can be whipped fresh when thawed, or if you freeze the sandwiches with frosting, thaw them slowly in the fridge overnight.

Reheating

Since these are cookies, reheating usually isn’t necessary, but if you prefer a slightly warm treat, let them come to room temperature or microwave for 10 seconds. Avoid warming too long or the frosting might melt and get messy.

FAQs

Final Thoughts

This Jack-O’-Lantern Sandwich Cookies Recipe has become one of my all-time favorites for fall — the aroma while baking, the fun of carving little faces, and the joy of biting into that soft pumpkin cookie with luscious cream cheese frosting. Whether you’re making them for a Halloween party or a cozy night in, they’re sure to bring smiles and maybe even a few cheeky “trick-or-treat” requests. Give this recipe a try — I think you’ll love it as much as my family does!

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