This Raisin Filled Cookies recipe is Nanny's and I make it pretty much the same way she did. The only things I changed are the butter (she used margarine) and the rum (she used water). It's a soft, old-fashioned cookie with a rum-spiked raisin filling in the middle, and it's one of those recipes that instantly puts me back in her kitchen.
- This is Nanny's raisin filled cookies recipe, the same one she made every winter - soft cookie, sweet rum-raisin filling, optional butter rum frosting if you want to dress them up.
- These are the kind of raisin filled cookies you'll see in a lot of Amish and Pennsylvania Dutch Kitchens, and once you make the filling yourself, you'll see why! It's simple, but it takes a little patience.
- I'll tell you the mistakes I've made with this recipe over the years (runny filling, dough that's too tough) so you don't have to learn the hard way.
- Plus, how I store these so they stay soft, and what to swap if you want to skip the rum or use dates instead of raisins.
Why You'll Love This Recipe
Memories in every bite: Each bite brings back being in grandma's kitchen with a warm raisin filled cookie in your hand!
Versatile: The cookie filling is easily adaptable to using your favorite dried fruits, nuts, or chocolate.
Soft filled cookies: Each cookie is soft with a delicious sweet rum flavored raisin filling!
Good for sharing: These hold up well, so they're great for a cookie tray, a lunchbox, or gifting. And, they're basically made for a holiday table with a hot buttered rum next to them.
Key Ingredients
You don't need anything fancy for these cookies, but a few ingredients are doing specific jobs:
- Sour milk is what keeps the cookie dough soft instead of crisp. Don't have any on hand? You can make your own: stir 1 tablespoon of white vinegar or lemon juice into a liquid cup measure, then fill to the ¾ cup line with milk. Let it sit for 5-10 minutes until it thickens slightly and looks a little curdled. You can also just swap the sour milk for buttermilk if you happen to have that in your fridge.
- Applesauce goes into the filling along with the raisins, and it's what helps the raisins plump up into a thick, jammy filling instead of staying dry or turning watery.
- Rum flavors both the filling and the frosting - see the swap outs below if you'd rather skip it.
- Baking soda and baking powder are both in this dough, not just one or the other. That combo is part of what gives these cookies their soft, slightly cakey texture instead of a crisp cookie snap.
- Beyond that, you've got your basics: butter, white and brown sugar, eggs, vanilla, salt, flour, raisins, and powdered sugar for the frosting. Exact amounts are all in the recipe card below.
Out of an Ingredient? Here's What I Use
Date filled cookies: Swap in chopped, pitted dates for the raisins.
Rum-free version: Use water in place of the rum in both the filling and the frosting.
Buttermilk: If you have this on hand, you can use this instead of sour milk.
How to Make Raisin Filled Cookies
To make raisin filled cookies, cook a thick raisin filling first, then sandwich a spoonful of it between two rounds of soft cookie dough, seal the edges with your thumb, and bake until golden. It's essentially a hand pie made with cookie dough instead of pie crust.
There are three parts to this one: the raisin filling, the cookie dough, and a butter rum frosting if you want it (you don't need it - I only frost a few of mine for looks). You make the filling first since it needs time to cook down and cool. Then you mix the dough, roll it out, sandwich a spoonful of filling between two rounds, seal the edges with your thumb, and bake.
It sounds like a lot of steps, but none of them are hard. The recipe card below has everything spelled out.
Raisin Filled Cookie Recipe: What you Need to Know
This dough behaves differently than a typical drop cookie because it has to hold a filling inside without falling apart. You roll the dough out thin and cut two rounds per cookie instead of scooping it like you would a chocolate chip cookie. You seal the edges by hand with your thumb, which also gives each cookie its slightly rustic, homemade look. They're not going to come out looking machine-perfect, and that's part of the charm. This recipe makes about 3 dozen, so it's a good one for a cookie tray or exchange.
Common Mistakes to Avoid
The dough gets tough if you overwork it once the flour goes in, so mix just until it comes together. Don't keep beating it.
The filling needs its full simmer time; if you rush it, it stays thin and will leak out of the cookies in the oven.
I use about a level tablespoon of filling per cookie - more than that and you'll have trouble sealing the edges.
And, keep an eye on the oven. A couple extra minutes past 20 and they go from soft to dry.
Tips for Raisin Filled Cookies Recipe
- Let the frosting sit for a bit before you use it. It thickens up and won't run down the sides as much.
- If you're stacking cookies to store them, put a piece of wax paper between the layers so the frosting doesn't stick to the next cookie.
- These keep at room temperature in an airtight container for about a week or so in the freezer for up to 3 months.
More Raisin Cookie Recipes
If you like raisins in your cookies, I've also got Oatmeal Raisin Walnut Cookies and Nanny's Soft Oatmeal Cookies. If you're into the rum flavor here, try my Banana Rum Coconut Raisin Cookies too.
Filled Cookie Questions Answered
They're the traditional Pennsylvania Dutch style - a soft cookie dough wrapped around a cooked raisin filling, more like a small filled hand pie than a regular drop cookie.
Yes, that's actually how Nanny made hers. Just swap water for the rum in the filling and milk for the rum in the frosting.
It probably needs more time on the stove. Keep it at a low simmer until it's thick enough to mound on a spoon, then let it cool.
Don't overfill. A level tablespoon per cookie is plenty - and press the edges firmly with your thumb to seal them before they go in the oven.
About a week at room temperature in an airtight container, or up to 3 months in the freezer.
When you make these raisin filled cookies, please comment below and let me know what you think. I'd love it if you tag me on Instagram @grumpyshoneybunch or #grumpyshoneybunch so I can see your photos!
If you love this recipe, please leave a ⭐⭐⭐⭐⭐ rating
📖 Recipe
Nanny's Raisin Filled Cookies
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Ingredients
For the cookies:
- ¾ cup unsalted butter softened
- 1 cup granulated sugar
- 1 cup light brown sugar
- 3 large eggs
- 1½ teaspoon vanilla extract
- 1 teaspoon baking soda
- 4 teaspoons baking powder
- ½ teaspoon salt
- 6½ cups all-purpose flour
- ¾ cup sour milk (or buttermilk)
For the Filling:
- 1 cup applesauce
- 1 cup raisins
- ½ cup brown sugar
- ¼ cup Captain Morgan's Spiced Rum or water
- 2 teaspoons butter
For the Frosting (OPTIONAL):
- 1 tablespoon unsalted butter melted
- 1 cup powdered sugar
- 1½ ounces Spiced rum OR milk
Instructions
For the filling:
- in a medium saucepan over medium heat, stir together the applesauce, raisins, brown sugar, rum, and butter.
- Bring raisin mixture to a boil, then turn heat down to low and simmer for 20-30 minutes, until mixture is thick and raisins have plumped.
- Set raisin mixture aside to cool.
For the cookie dough:
- Preheat oven to 350 degrees F. Line a large cookie sheet with parchment paper and set aside.
- In a large bowl, using an electric mixer, mix together butter, white sugar, and brown sugar creamy.
- Add eggs, one at a time and mix until well blended after each addition. Stir in vanilla extract.
- In a separate bowl, mix together flour, baking powder, baking soda, and salt.
- Add dry ingredients to wet ingredients 1 cup at a time. Add sour milk a little at a time after each flour addition.
- By the time you are ready to add your last cup of flour, the dough should be sticky, but starting to stiffen some. Once you have added 6 cups, roll dough out onto a floured board and lightly knead the remaining ½ cup of flour into the dough.
- Divide dough into quarters and using a rolling pin, roll out to about ⅛-inch thickness on a floured surface. Using a round cookie cutter, cut two cookie rounds out for each cookie.
- Place 1 cookie dough round on cookie sheet. Top with 1 tablespoon of raisin filling. Place another cookie round on top of cookie with filling. Press with thumb to seal.
- Bake for 17-20 minutes or until lightly golden brown. Transfer cookies to cooling rack and cool completely.
For the Frosting (Optional)
- In a medium bowl, using an electric mixer, combine the butter, powdered sugar, and rum together until well combined.
- Add more sugar or rum as needed to make frosting thin enough to run just a little when frosted.
- Let frosting sit while cookies are cooling and it will thicken up some and not run down the sides of cookie when frosting.
Notes
Nutrition
Doro N says
Delicious. Makes lots of cookies. I made half fig and the other half raisin and still had extra dough that I filled with strawberry preserves. The icing is pretty, but the cookies are sweet enough without any. Also, the only spirits I had were apricot brandy. Worked great.
Shelby Law Ruttan says
Thank you for trying the recipe and for sharing your experience, I love you used figs as well! I agree, the icing is pretty and not needed, but those die hard icing lovers in my family are always happy to find some with the icing. I always make some with and without it. Thanks again!
Judy says
I have been making these for my family for 50 years, but no frosting and three slits in the top. My boys always called them “three holers “ the only difference is I use cream of tarter and no applesauce. They are delicious.
Kathleen QUINN says
Can I make the dough and/or filling and freeze them?
Shelby Law Ruttan says
You could make the cookies, fill them, and then freeze before baking, or you could bake them, then freeze them in an airtight container up to 3 months. Feel free to email me if you have any questions! Shelby
Connieph9 says
These were just like I remembered from Oakmont Bakery in PIttsburgh. I had leftover frozen peaches and some chestnut spread so made the three different fillings. Thanks for sharing- I loved them! Also love your Rhubarb Keto dream bars 🙂
Shelby Law Ruttan says
Hi Connie! Thank you so much for sharing, love that you made different fillings and happy you love the Rhubarb Keto Dream Bars also 🙂 Shelby
Polly Hastings says
Hi Shelby, I am a new subscriber to your website! Looking forward to exploring your recipes! My Mother in the 1950s and 60s made these exact same cookies with a prune filling. Do you suppose I could substitute the prunes for the raisins without much fuss or changes? Have you heard of prune filled cookies? Mother's cookies looked exactly like yours. Polly
Shelby says
Hi Polly, I think you could probably use prunes, but may need to increase the sugar a little since they aren't as sweet as raisins. Thanks for subscribing and I hope you enjoy my posts!
Ken Mitts says
I am 80 years old and live in Texas. I grew up in Pennsylvania and love raisin filled cookies but cannot buy theme here. Could you possibly tell me where I can buy them and have them shipped to me.
Shelby Law Ruttan says
Hi Ken, I would be honored to make some and send them to you...free of charge! If you email me your address, I will make some and ship them asap! Thanks for stopping by and commenting! Shelby
P.S. My dad is also 80 years old, he will be 81 next month!
Jeri Tachappat says
These are childhood memories for me also. My Grandparents were deceased before I was born. My Mother used to make these and someone lost the recipe . The only thing different that I remember is I used to help Mother grind the raisens, grinder hooked onto the edge of the table, I still have her grinder. Thank you so very much.
You say sour milk, would that be milk with vinegar or lemon?
Shelby says
Hi Jeri, Thank you 🙂 Yes. I mean milk with vinegar or lemon.
Cheryl says
This looks like my Grandma's most-loved cookie. She always made two batches for holidays: 1. date-filled, + 1. apricot-filled. I'd be willing to bet she used what she called 'oleo' too. She also had a trick to form them more efficiently: instead of picking up another disc, she'd use a bit less filling, and fold them over turnover-style. Thank you so much for posting the recipe; I can't wait to try it.
Shelby says
Hi Cheryl, I hope you enjoy the cookies! My mom used to fold the cookie in half also for turnovers 🙂
Lauren @ Sew You Think You Can Cook says
My grandma didn't have a "cookie jar" (although she made incredible cookies) but she had a "candy drawer" that we were always eager to delve into.
I love how close your family is, and that your boys got the opportunity to know their great-grandparents in an intimate way. <3
Caroline | carolinescooking says
What lovely memories you have shared, and so nice that you got to spend so much time with them. These cookies look great as well. I am not sure I have had filled cookies quite like this before (although British mince pies are along the same lines, just more filling) but they look and sound great!
Cindys Recipes and Writings says
Boy Shelby do these ever bring back sweet memories!
cathy branciaroli says
My grandmother made a raisin bar, not a cookie, and while everyone raves about them, no one remembers how they were made - darn!
Serena | Serena Bakes Simply From Scratch says
Wonderful!
Laura Dembowski says
These cookies sound delightful. I love that you added frosting and those fun sparkles.
Sarah | Curious Cuisiniere says
These sound amazing! They're going on my Christmas cookie list for sure!
Liz says
Oh, what sweet memories! And your cookies look like the perfect autumn treat!
Susan 30A Eats says
What a sweet post, and I'm not just talking about the cookies, though I could devour a bakers dozen right now!
Wendy, A Day in the Life on the Farm says
How lucky you were to have such a great relationship with all of your grandparents. I only had my Mom's mom but the memories are priceless. I love these cookies. Thanks for the recipe.
Stacy says
You brought tears to my eyes, Shelby. What a sweet post and delightful cookies!
claudia says
These sound so good Shelby can't wait to try them I love that filling with Morgan in it! WOW!