These Filled Raisin Cookies are more than just a Christmas treat; they are a piece of living family history, carefully preserved through generations. This is the one recipe my dad asks for every Christmas, year after year, without fail. No fancy desserts, no trendy cookies—just these humble, old-fashioned filled raisin cookies, made exactly the way his mother made them, and likely the way her mother made them before her. Baking them has become a tradition rooted in love, patience, and deep respect for the past.
This recipe comes from a time when instructions were written with intuition in mind rather than exact measurements. Phrases like “heaping teaspoons of baking powder” and “enough flour to roll” were standard because bakers relied on experience, feel, and instinct. Over the years, through trial and error, this recipe has been gently refined and clarified while still honoring its original spirit. What you’ll find here is a faithful, carefully documented version of that heirloom recipe—organized, professional, and ready to be shared, yet still deeply traditional at heart.
These cookies are soft and tender, almost cake-like, wrapped around a thick, jammy raisin filling scented with fresh orange zest and studded with chopped pecans. Each cookie is assembled like a tiny hand pie, sealed carefully so the filling stays tucked inside while baking. They take time to make, but that time is part of what makes them so special. This is not a rushed recipe. It’s a labor of love.
Because they freeze beautifully, these cookies are often made in large batches and portioned out to last all year long. Pulling a container from the freezer months later feels like opening a small box of memories—proof that some traditions are worth preserving exactly as they are.
OLD-FASHIONED FILLED RAISIN COOKIES
Ingredients
For the Cookie Dough (Creamed Mixture)
2 cups granulated sugar
1 cup Crisco shortening
4 large eggs
2 teaspoons salt
1 tablespoon vanilla extract
1 cup milk
For the Dry Ingredients
3 rounded teaspoons baking powder
Approximately 7 cups all-purpose flour
Note: Begin with 6 cups of flour and add more gradually until the dough reaches the correct rolling consistency.
For the Raisin Filling
3 boxes raisins (12 ounces each; some filling may remain)
1/2 cup granulated sugar
3 tablespoons cornstarch
Finely grated zest of 1 medium orange
1 1/2 cups chopped pecans
Enough water to just cover the raisins
Preparing the Raisin Filling
Always begin by making the filling first. It needs time to cool before assembling the cookies, and working with warm filling will make the dough difficult to handle.
Place the raisins, sugar, orange zest, and enough water to just cover the raisins into a medium saucepan. Set the pan over medium heat and bring the mixture to a healthy simmer, stirring frequently to prevent sticking or scorching. Allow it to simmer for several minutes, until the raisins soften and plump.
In a small bowl, whisk the cornstarch with a little cold water until completely smooth and free of lumps. Slowly pour this mixture into the simmering raisins while stirring constantly. Continue simmering until the filling thickens to a spoonable, jam-like consistency.
Remove the pan from heat and stir in the chopped pecans. Set aside and allow the filling to cool until no longer hot.
Making the Cookie Dough
In a large mixing bowl, cream together the sugar and Crisco shortening until light and fluffy. This step is important for creating a tender cookie texture.
Add the eggs one at a time, mixing well after each addition. Stir in the salt and vanilla extract.
Gradually add the milk, mixing until fully incorporated.
In a separate bowl, sift together the flour and baking powder. Begin adding the dry ingredients to the creamed mixture, starting with about six cups of flour. Mix until combined, then add additional flour a little at a time until the dough becomes soft, pliable, and easy to roll without sticking.
Turn the dough out onto a well-floured surface and knead gently just until smooth. Avoid overworking the dough, as this can result in tough cookies.
Rolling and Assembling the Cookies
Preheat the oven to 375 degrees Fahrenheit. Line baking sheets with parchment paper to catch any filling that may bubble out during baking.
Roll the dough out on a well-floured surface to a thickness between 1/8 and 1/4 inch. The dough should be thin but sturdy enough to hold the filling.
Using a round cutter approximately 3 inches in diameter, cut circles from the dough. Gather and re-roll scraps as needed.
Place one leveled scoop of raisin filling in the center of each dough round. A small cookie scoop works well, but a rounded teaspoon is also effective. Gently pat the filling down slightly.
Moisten the edges of a second dough round with a small amount of water. Place it on top of the filled round and press the edges together firmly to seal. Crimp with a fork or use a cut-and-seal tool if available.
Transfer the assembled cookies carefully to the prepared baking sheets, leaving space between each cookie.
Baking Instructions
Bake the cookies in the preheated oven for approximately 20 minutes, or until set and very lightly browned. These cookies should remain pale and soft rather than deeply golden.
Remove from the oven and allow the cookies to cool completely on the baking sheets before transferring them to storage containers.
Storage and Freezing
Once completely cooled, store the cookies in an airtight container. They keep well at room temperature for several days.
For longer storage, these cookies freeze exceptionally well. Layer them between sheets of parchment paper in airtight freezer containers. Thaw at room temperature as needed.
This recipe yields approximately four dozen cookies, depending on size and thickness. Any leftover filling can be used as a pie or strudel filling, spooned over toast, or swirled into pastry dough.
Why This Recipe Endures
These Filled Raisin Cookies are not flashy or trendy. They are timeless. They represent family gatherings, holiday kitchens filled with warmth, and traditions that have survived decades. Each cookie is a reminder that the most meaningful recipes are often the ones that take the most time and care.
Making these cookies is about more than baking. It is about honoring the hands that made them before us, preserving memories, and passing something meaningful on to the next generation. If you are lucky enough to have a recipe like this in your family, treasure it. And if this is your first time making filled raisin cookies, may it become a tradition you carry forward for years to come.