Halloween Date Filled Cookies: 120 Delicious Bites

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

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Preheat oven to 375°F (190°C).
Cream shortening and sugars until fluffy. Add egg, milk, and vanilla. Mix well.
Sift flour, baking soda, and salt, then add to the wet mixture. Chill dough for at least 1 hour for easier rolling.
In a saucepan, combine chopped dates, sugar, and water. Bring to a boil, cover, and simmer for 5 minutes, stirring occasionally. Add lemon juice and salt. Let the mixture cool before using.
On a lightly floured surface, roll out half the dough to just under 1/8 inch thick. Cut shapes using a 2 1/2-inch round cookie cutter or Halloween-themed cutters.
Place one tablespoon of date filling in the center of each base cookie. Top with another cookie round, pressing the edges with a fork to seal.
Arrange cookies on an ungreased baking sheet and bake for 10–12 minutes, or until lightly golden. Cool before serving.

Chill the dough thoroughly for easier handling and rolling.
Avoid overfilling the cookies to prevent leakage during baking.
Use fun Halloween-shaped cutters for a festive look.
For a spooky effect, cut small shapes like eyes or a jack-o’-lantern smile in the top cookie layer.
Consider using parchment paper on your baking sheets for easier cleanup.
Adding oatmeal to the dough creates a heartier cookie.
Mixing chopped nuts into the filling adds a delightful crunch.
A drizzle of melted dark chocolate over cooled cookies offers an indulgent touch.