Take a nostalgic trip down memory lane with these Old Fashioned Raisin Filled Cookies, a timeless treat that brings together a soft, buttery cookie dough and a perfectly spiced, homemade raisin filling. Each bite is a delightful balance of sweetness, warmth, and chewy texture, thanks to a luscious raisin mixture thickened with cornstarch and encased in golden, crimped-edged cookie shells. This recipe is simple yet elegant, featuring classic ingredients like brown sugar, vanilla, and creamy butter to create a rich, comforting cookie that’s perfect for holidays, afternoon tea, or anytime indulgence. With step-by-step instructions and a prep-and-bake time of under an hour, these cookies are as rewarding to make as they are to share. Perfect for traditional baked goods enthusiasts, these raisin-filled cookies will quickly become a cherished favorite in your family’s recipe collection.
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In a small saucepan, combine the raisins, granulated sugar (for filling), and water. Bring to a simmer over medium heat and cook for 5 minutes until the raisins are soft.
Whisk the cornstarch with 1 tablespoon of water to make a slurry. Add it to the raisin mixture, stirring constantly until it thickens. Remove from heat and let the filling cool while preparing the cookie dough.
In a mixing bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.
In a large bowl, cream the butter, granulated sugar (for dough), and brown sugar together until light and fluffy using a hand or stand mixer.
Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
Gradually mix in the dry ingredients, alternating with the milk, beginning and ending with the dry ingredients, until a soft dough forms. Divide the dough in half, wrap in plastic wrap, and chill for 20 minutes.
Preheat the oven to 375°F (190°C) and line baking sheets with parchment paper.
Roll out one half of the chilled dough on a floured surface to about 1/8-inch thickness. Use a round cookie cutter (approximately 3 inches in diameter) to cut out circles.
Place half of the circles onto the prepared baking sheets. Spoon about 1 teaspoon of the cooled raisin filling onto the center of each circle, leaving a small border around the edges.
Top with another dough circle and press the edges together gently to seal. Use the tines of a fork to crimp the edges for an added decorative touch. Cut a small slit in the top of each cookie to allow steam to escape.
Repeat with the remaining dough and filling, re-rolling the scraps as needed.
Bake in the preheated oven for 10-12 minutes, or until the cookies are lightly golden around the edges.
Allow the cookies to cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely. Enjoy!
Serving size | (1527.1g) |
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Amount per serving | % Daily Value* |
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Calories | 4901.2 |
Total Fat 112.6g | 0% |
Saturated Fat 61.4g | 0% |
Polyunsaturated Fat 0.2g | |
Cholesterol 631.0mg | 0% |
Sodium 1947.4mg | 0% |
Total Carbohydrate 935.0g | 0% |
Dietary Fiber 18.7g | 0% |
Total Sugars 582.4g | |
Protein 66.1g | 0% |
Vitamin D 135.7IU | 0% |
Calcium 461.0mg | 0% |
Iron 25.1mg | 0% |
Potassium 2106.6mg | 0% |
Source of Calories