Nanny's Raisin Filled Cookies are an old fashioned cookie recipe with a soft cookie dough filled with a rum soaked sweet raisin filling . This raisin cookie is one of my favorite cookies my Nanny would make and brings a little bit of nostalgia with every bite.
❤️ Why you'll love it
Memories in every bite: each bite brings back being in grandmas 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!
🥘 Ingredients
Unsalted butter
White sugar
Light brown sugar
Large eggs
Pure Vanilla extract
Baking soda
Baking powder
Salt
All-purpose flour
Sour milk
Applesauce
Raisins
Rum
Powdered sugar
🔪 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. Lin 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.
To Make the Frosting
- 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.
🥄 Equipment
Medium saucepan
Wooden spoon
Large cookie sheet
Large Bowl
Medium bowl
Electric mixer
Rolling pin
Parchment paper
Tablespoon
Cooling rack
🥫Storage
Room temperature: store cookies in an airtight container up to 1 week.
Freezer: store in a freezer safe container up to 3 month.
📖 Variations
Date filled cookies: substitute chopped, pitted dates for the raisins.
Rum free version: substitute water for the rum
💭 Tips
- Allow frosting to dry completely before storing cookies.
- When storing cookies, place a piece of wax paper over each layer to prevent frosting from sticking to stacked cookies.
📚 Related Recipes
If crispy edges with chewy centers are your thing, then you want to try these Oatmeal Raisin Walnut Cookies.
This recipe for Nanny's Soft Oatmeal Cookies are another childhood favorite.
If you love rum in your sweet treats, then these Banana Rum Coconut Raisin Cookies are a must try!
My whole family loves this Best Carrot Cake with Raisins and Walnuts.
🍽 Serve with...
Serve cookies with a glass of milk, cup of hot coffee or a hot buttered rum! They also are perfect for holiday gatherings, their versatile nature makes them a delightful treat all year round.
Don't forget to check out my Amazon storefront for some of my favorite products!
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
- 1-½ teaspoon vanilla extract
- 1 teaspoon baking soda
- 4 teaspoons baking powder
- ½ teaspoon salt
- 6-½ cups all-purpose flour
- ¾ cup sour milk
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:
- 1 tablespoon unsalted butter melted
- 1 cup powdered sugar use more if needed
- 1 shot 1-½ ounce Captain Morgan's Spiced Rum
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. Lin 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
- 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
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!