Pap Steve’s Old-Fashioned Raisin-Filled Sugar Cookies

(The “moderate oven” version, straight off the old recipe cards)

PapSteveReviews.com – October 2026

Pap Steve here. Some recipes come from cookbooks. The good ones come from a stack of handwritten family recipe cards, the kind with grease spots, faded ink and directions like “bake in a moderate oven” that assume you already know what you’re doing. That’s where these Old-Fashioned Raisin-Filled Sugar Cookies came from. This is Grandma Alice’s recipe, and it came to her from her mother. Every generation since has kept it going.

The cards have a story of their own. The filling card is in my mother’s own handwriting. The original dough card was all but destroyed over the years, so my brother transcribed a new one in his handwriting. Look closely at that card and you’ll see the one snag every old family recipe has: the flour line just says “flour.” No amount. Back in the old days they really didn’t measure things. They just added flour until it felt right!

That’s fine if you learned at Grandma’s elbow, but the rest of us need a number. So we validated the flour against modern sugar cookie recipes and landed on 5 to 6 cups. Start with 5 and add more until the dough is soft but rollable. No guesswork beyond that, no fluff.

My mother made these every Christmas. One bite and I’m a kid again, standing by the Christmas treat table and trying to figure out how many I could grab before somebody noticed. All of my siblings love these cookies too, so if you want to know what our family Christmas tastes like, this is it.

Makes: 20 to 40 cookies, depending on how big you cut the base and the top
Difficulty: Weekend project. Not hard, just a few moving parts.

Pap Steve

Old-Fashioned Raisin-Filled Sugar Cookies

Grandma Alice's raisin-filled sugar cookies, handed down from her mother. Soft nutmeg sugar cookie dough wrapped around a cooked raisin filling.

Print Recipe Pin Recipe

Servings: 30 cookies

Course: Dessert

Cuisine: American

Ingredients Method Notes

Ingredients

  

Cookie Dough

• 2 eggs beaten
• 2 cups sugar
• 2 cups shortening
• 1 cup milk
• 2 tsp baking soda
• 2 tsp cream of tartar
• 1 tbsp nutmeg per the cards; start with 1 tsp and work up to taste
• 5-6 cups all-purpose flour start with 5; add until soft but rollable

Raisin Filling

• 1 1/3 cups sugar
• 1 cup hot water
• 2 tbsp butter
• 1 tbsp flour
• 1/4 tsp salt
• 4 cups raisins

Method

 

Make the Filling First

1. Combine the sugar, hot water, butter, flour, salt and raisins in a saucepan.
2. Bring to a boil over medium heat and stir until thickened, about 5-10 minutes.
3. Remove from heat and cool completely before using.

Make the Dough

1. Mix the eggs, sugar, shortening and milk.
2. Stir in the baking soda, cream of tartar and nutmeg.
3. Gradually add the flour, starting with 5 cups, until the dough is soft but manageable for rolling. Chill if needed.
4. Roll out on a floured surface and cut into circles.

Fill, Seal and Bake

1. Heat the oven to 350 F.
2. Place a spoonful of cooled filling in the center of half the cutouts and top with the remaining cutouts.
3. Seal and crimp the edges.
4. Bake until golden, about 10-12 minutes.
5. Cool on a wire rack.

Notes

Yield: 20-40 cookies, depending on how big you cut the circles and how much filling you use.

• These are nutmeg-heavy. The cards call for a full tablespoon. Start with 1 teaspoon and work your way up.
• The flour on the old card just says “flour.” We validated 5 to 6 cups against modern sugar cookie recipes. Start with 5.
• Make the filling a day ahead and keep it in the fridge. Cold filling is easier to spoon.
• As with all recipes handed down generation to generation, details shift!

Pap Steve’s Tips

Chill the dough.
A soft, shortening-heavy dough rolls much easier after some time in the fridge. If it fights you, chill it.

Go easy on extra flour.
Add it a little at a time. Too much makes a tough cookie instead of a tender one.

Crimp with a fork.
Press the edges with fork tines so the filling stays put. A dab of water or milk on the bottom edge helps it seal.

Cut a vent.
A small slit or hole in the top cookie lets steam escape and shows off the filling.

Don’t overfill.
Too much filling squeezes out the sides when you seal.

Storage.
Keep cooled cookies in an airtight container at room temperature for a few days, or freeze them for longer.

Pap Steve’s Field Notes

• Chill the dough. A soft, shortening-heavy dough rolls much easier after some time in the fridge. If it fights you, chill it.
• Go easy on extra flour. Add it a little at a time. Too much makes a tough cookie instead of a tender one.
• Crimp with a fork. Press the edges with fork tines so the filling stays put. A dab of water or milk on the bottom edge helps it seal.
• Cut a vent. A small slit or hole in the top cookie lets steam escape and shows off the filling.
• Make the filling a day ahead. Cover and refrigerate it. Cold filling is easier to spoon and it splits the job into two easy days.
• That nutmeg is strong. These are nutmeg-heavy. The cards call for a full tablespoon, which is old-school bold. Adjust to taste: start with a teaspoon and work your way up. As with every recipe handed down generation to generation, the details shift!
• Don’t overfill. Too much filling squeezes out the sides when you seal.
• Storage. Keep cooled cookies in an airtight container at room temperature for a few days, or freeze them for longer.

Recipes like this don’t survive on their own. Somebody has to pull the cards out of the box and bake them. Grandma Alice’s mother started it, Grandma Alice kept it going, and my mother put these on the table every Christmas. Now it’s our turn. Now get that oven to moderate. Got an old family recipe card with a mystery measurement? Drop it in the comments.

God Bless Y’all,
Pap Steve
PapSteveReviews.com