Jack-O'-Lantern Sandwich Cookies

Pumpkin spice sugar cookies sandwiched with tangy cream cheese frosting make the most festive Halloween treat. Carving goofy or spooky faces into these Jack O Lantern sandwich cookies turns baking into a creative project. Homemade always disappears faster than store bought around here and these are as fun to make as they are to eat.

I made these for my niece’s Halloween sleepover and all the kids insisted on decorating at least two each The laughter and friendly competition over the scariest cookie was the real treat

Ingredients

• All purpose flour: gives the cookies structure and bite Choose a high quality unbleached brand for best results
• Pumpkin spice: adds classic fall warmth If possible pick a fresh blend for maximum aroma
• Baking powder: ensures the cookies puff up softly without being cakey Check expiration for best leavening
• Kosher salt: enhances flavor and balances sweetness Opt for fine grain for even mixing
• Butter: provides richness and tenderness Always use unsalted and allow to fully soften for creaminess
• Granulated sugar: gives lift and lightness Use a clean white sugar for consistent results
• Brown sugar: brings extra moisture and flavor Look for soft and clumpfree brown sugar
• Egg: binds the dough and adds tenderness Farm fresh or organic gives the brightest flavor
• Pumpkin puree: gives flavor color and softness Always use pure pumpkin not pie filling
• Vanilla extract: enhances all the spices Choose a pure extract for best depth
• Cream cheese: brings tang and richness to the frosting Use full fat blocks for the dreamiest texture
• Powdered sugar: sweetens and smooths the filling Sift for lump free results
• A pinch of salt in frosting: helps balance that classic tang Choose a clean kosher style for best effect

Step by Step Instructions

Make the Dough:

In a large mixing bowl whisk together flour pumpkin spice baking powder and salt until fully combined This creates your dry ingredient base

Cream the Butter and Sugars:

In a separate mixing bowl use a hand mixer to blend softened butter granulated sugar and brown sugar until very creamy and fluffy This step creates an airy texture for pillowy cookies

Add Egg Pumpkin and Vanilla:

Beat an egg until fully incorporated then blend in pumpkin puree and vanilla mixing again until smooth The batter will look slightly orange and glossy

Combine and Chill:

Slowly add your dry ingredients to the wet mixture Beat just until no flour streaks remain Take care not to over mix Split dough into two discs shape and wrap tightly Chill for at least two hours or up to three days Chilling ensures cookies hold their shape

Shape and Cut:

On a well floured surface roll out one dough disc to about one quarter inch thick Using a pumpkin shaped cookie cutter cut out as many cookies as possible Place cutouts onto parchment lined baking sheets Re roll scraps and repeat When all are cut freeze trays for fifteen minutes for sharpest shapes

Carve Faces and Prepare to Bake:

Set oven to three hundred fifty degrees Carve faces into half of the cookie cutouts using a small paring knife If the dough softens too much refreeze tray briefly to make carving easier and prevent spreading

Bake the Cookies:

Slide trays into the oven Bake cookies for eight to ten minutes until just set and lightly golden Let cool completely on sheets before moving This helps them hold their form

Mix the Frosting:

Blend softened cream cheese with powdered sugar in a clean bowl using a mixer until smooth and lump free Beat in vanilla and a pinch of salt for tangy balanced flavor

Assemble the Sandwiches:

Flip cookies without faces over and generously spread with cream cheese frosting Top each with a matching faced cookie gently pressing so the filling peeks through

Pin

My absolute favorite part is carving silly and scary faces into the dough My family laughs for ages at each other’s creative fails and the taste always brings everyone back together at the table I love sneaking a spoonful of the cream cheese frosting when nobody is looking

Storage Tips

Keep finished cookies in an airtight container in the fridge They stay soft and fresh for up to five days To serve at a party let them come to room temperature for best frosting texture The unfilled cookies can be frozen for a month then sandwiched fresh for an easy shortcut

Ingredient Substitutions

Neufchâtel can replace cream cheese for a slightly lighter frosting Feel free to swap in homemade pumpkin spice blend for extra depth If out of pumpkin puree pureed sweet potato works nicely in a pinch Dairy free butter and vegan cream cheese hold up well for plant based bakers

Serving Suggestions

These Jack O Lantern cookies shine at Halloween gatherings and bake sales Arrange them on a dark platter with handfuls of candy corn or edible candy eyes for maximum impact Pair them with cups of hot cider or chai for the ultimate autumn treat Mini sandwiches make cute party favors too

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Cultural Context

Pumpkin shaped treats have roots in American fall festivals where pumpkins symbolize harvest and community creativity Carved pumpkins also known as Jack O Lanterns are a staple of Halloween which dates back to old Celtic traditions These cookies blend classic American sugar cookie dough with pumpkin spice for seasonal nostalgia

Frequently Asked Questions About the Recipe

→ What ingredients give these cookies their autumn flavor?

The warm notes come from pumpkin puree combined with pumpkin spice, which includes cinnamon, nutmeg, and cloves that give a cozy fall aroma.

→ How can I keep the cookie shapes firm during baking?

Chilling the dough for at least two hours before cutting and baking helps maintain crisp pumpkin shapes and prevents spreading.

→ Can I prepare the cookies in advance?

Yes, the dough can be refrigerated for up to three days or frozen after cutting, allowing flexible preparation timing.

→ What is the best way to apply the frosting?

Spread the cream cheese frosting on the cookie without cut-out faces, then carefully top with a decorated cookie to create a sandwich.

→ How long should I bake these cookies?

Bake them at 350°F (175°C) for 8 to 10 minutes until set but not browned, preserving their soft texture and shape.