Super Easy Chocolate Stuffed Jack O’Lantern Sandwich Cookies for Halloween

Jack O'Lantern Sandwich Cookies are delicious and original desserts that we have made in the shape of the famous Jack O'Lantern figure with a delicious hazelnut cream filling: perfect for celebrating October 31st, the scariest night of the year, they will be loved by adults and children alike.

To obtain crumbly and fragrant cookies we prepared the shortcrust pastry with egg yolks, butter, sugar, flour, lemon zest and salt, we then divided the dough in two, adding a drop of orange food coloring to one part, to recall the color of the pumpkin. The mixture will then be rolled out and we will obtain the biscuits with pumpkin-shaped cutters, creating a top and a bottom. The biscuits will then be baked in the oven for 15 minutes and filled with hazelnut cream , ready to be enjoyed: prepare them to end the Halloween menu in style.

What Are Jack O'Lantern Sandwich Cookies?

Sandwich cookies, originating in the early 1900s, were popularized by the Oreo in 1912 and quickly became an iconic treat worldwide. Jack o' lantern cookies, shaped to resemble the carved pumpkins of Halloween folklore, nod to the old Irish legend of “Stingy Jack”—a man doomed to wander the earth with a hollowed-out turnip lantern after tricking the Devil one too many times. When Irish immigrants arrived in the U.S., pumpkins replaced turnips, creating the jack o’ lantern we know today. Fun fact: carving jack o’ lanterns was meant to ward off evil spirits, but now, it’s a symbol of spooky fun and a tasty inspiration for festive treats like these cookies!

Pro Tips for The Best Jack O'Lantern Sandwich Cookies

• Cold butter helps the dough stay firm and easier to handle, preventing it from getting too sticky.
• After mixing, wrap and chill both doughs for at least 30 minutes to make rolling and cutting shapes easier.
• Use a rolling pin to ensure an even thickness, so the cookies bake consistently.
• Bake just until the edges are lightly golden—over-baking can make them too crunchy to sandwich easily.
• Allow cookies to cool completely before adding hazelnut cream to avoid melting and mess.
• A small amount of hazelnut cream will help the cookies stick without squishing out the sides.

Do I Need Artificial Food Dye or Can I Use a Natural Alternative?

You don’t need to use artificial food dye; there are great natural alternatives! For a warm orange hue, try using carrot or pumpkin powder, turmeric (in very small amounts), or beet powder mixed with a touch of yellow for balance. The taste won't be altered, using these alternatives!

Why Are My Cookies All Crumbly?

If your cookies turn out crumbly, it’s likely due to over-mixing or too little moisture. Over-mixing the dough develops gluten, making the cookies dry and crumbly. Also, ensure you’re measuring ingredients accurately; too much flour or too little butter can affect texture. Chilling the dough helps it hold together, so don’t skip that step!

What If I Don't Have A Cookie Cutter?

No cookie cutter? No problem! Use a drinking glass rim for round shapes, or carefully cut out shapes with a knife. For the jack o’ lantern details, try using a small paring knife or a bottle cap for the eyes and mouth—it adds a rustic, homemade touch to your cookies!

Help! Why Didn't My Cookies Hold Their Shape?

If your cookies didn’t hold their shape, the dough might have been too warm or soft. Make sure to chill it thoroughly before cutting shapes, and if it softens as you work, pop it back in the fridge briefly. Also, avoid over-mixing the dough, which can make it spread. Keeping your oven at the correct temperature is essential, too, for a perfect hold during baking!

What Else Can I Use for Stuffing The Cookies?

You can stuff these cookies with all kinds of tasty fillings! Try chocolate ganache, caramel spread, fruit jam, or even a cream cheese frosting for a delicious twist.

Can I Add a Glaze?

Yes, you can definitely add a glaze! A simple powdered sugar glaze with a hint of vanilla or lemon works beautifully. Just make sure the cookies are completely cool before glazing, and let the glaze set before serving for a neat finish.

Can I Make These Cookies Ahead of Time?

Yes, you can! Bake and store the unfilled cookies in an airtight container for up to a week. For the best texture, fill them with hazelnut cream or other fillings just before serving.

Do These Cookies Freeze Well?

Good news: you can! For best results, freeze the unfilled cookies in an airtight container for up to three months. When ready to enjoy, simply thaw at room temperature and fill them with hazelnut cream or your chosen filling.

How to Store Jack O'Lantern Sandwich Cookies

You can store any leftover already stuffed cookies for 2 days in a tin or under a glass bell jar.

How to Make Jack O'Lantern Sandwich Cookies

In a bowl add the butter, sugar and lemon zest.

Mix the ingredients with an electric whisk until the sugar dissolves and you obtain a creamy mixture.

At this point add the salt, the egg yolks and keep stirring.

Finally, pour the flour.

Knead until you obtain a smooth and compact dough.

Divide the dough into two halves. In one add the food coloring (or the natural alternative) to make the dough orange.

Wrap both loaves in cling film and then let them rest in the fridge for 30 minutes, at least.

Then roll out both doughs using a rolling pin.

Using the pumpkin-shaped cookie cutters (base and face of the pumpkin) to cut out the various shapes.

Transfer the cookies onto a parchment paper lined baking tray and bake them in the oven at 360°F (180°C) for 15 minutes.

Spread the hazelnut cream on the base and then place the cookies with the pumpkin face right on top to form the sandwiches.

Serve them all together. Enjoy!