Halloween Date Filled Cookies: Spooky & Sweet Treats

Soft and chewy Halloween Date Filled Cookies with a sweet, gooey date center, perfect for fall baking and festive parties.

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Preheat your oven to 375°F (190°C).
Cream together the shortening and both sugars until fluffy. Add the egg, milk, and vanilla, mixing well.
Sift the flour, baking soda, and salt. Add these dry ingredients to the wet mixture. Blend until smooth.
Chill the dough for at least one hour for easier rolling.
In a saucepan, combine the chopped dates, sugar, and water. Bring to a boil, then cover and simmer for 5 minutes, stirring occasionally.
Stir in the lemon juice and salt. Let the date filling mixture cool before using.
On a lightly floured surface, roll out half the dough to just under 1/8 inch thick. Use a 2 1/2-inch round cookie cutter to cut shapes. For a spooky Halloween touch, use pumpkin, bat, or ghost cutters.
Place one tablespoon of the prepared date filling in the center of each base cookie.
Top with another cookie round. Press the edges with a fork to seal them.
Arrange the assembled Halloween date filled cookies on an ungreased baking sheet.
Bake for 10–12 minutes, or until lightly golden.
Cool the cookies completely before serving.

Chill the dough thoroughly for easier rolling and to prevent sticking.
Do not overfill the cookies; 1 tablespoon of date filling per cookie is ideal to prevent leakage.
Use fun Halloween-shaped cutters for a festive appearance.
Consider cutting small shapes like eyes or a jack-o’-lantern smile into the top cookie layer for a spooky effect.
Using parchment paper can make cleanup easier.
For an oatmeal version, add 1 cup of rolled oats to the dough.
For a nutty twist, mix chopped walnuts or pecans into the date filling.
Drizzle melted dark chocolate over cooled cookies for an indulgent touch.