Nannys Raisin Filled Cookies

Nannys Raisin Filled Cookies are an old-fashioned soft cookie filled with a sweet raisin filling and slightly enhanced with my own addition of rum. This cookie that brings back memories from your childhood that you never want to forget along with all the love attached to it.Nanny's Soft Filled Raisin Cookies

This week, the Sunday Supper Tastemakers are sharing recipes passed down from our Grandparents in honor of Grandparent’s Day. This old-fashioned cookie that my Nanny liked to make is my contribution in honor of all of my grandparents. I did change her recipe a little, but only by adding rum in the raisin mixture rather than water and using butter instead of margarine.


Nanny's Raisin Filled Cookies

What I remember the most about my Grandpa Law was his big happy smile, his fun-loving nature, and his love of music. I remember going to visit and he would pull the fiddle out to play. My Grandma Law was much quieter. She loved her dogs and I can remember her knowing that they scared the living life out of me when they would bark! (She had big dogs, by the way, not little ones!) She would be sure to hold on to them until we got in the house and settled in. Then all would be good.

Poppy Whitton loved every single one of his grandchildren and they knew it. He loved to go out to eat and one of us always loved to be with them when they did. We often went to Dixie Lee and when that place was no more he loved to go to Kentucky Fried Chicken. I do remember going to places like the Dairy Queen and McDonalds with them, but those fried chicken places were where he loved to go most. He would tolerate a lot of things, one being me sitting on the wooden arm of his chair. I’d suck my thumb and reach up to that little bit of hair he had on the top of his head and twirl it right into a knot. Poor Pop! He didn’t care though. He loved the attention and affection.
Nanny's Raisin Filled Cookies

Nanny is one of the reasons I write my blog. For years and years I called my Nanny “grandma”. It is only after Justin was born that she became “Nanny.” Justin and Christopher were lucky enough to get to know several of their great grandparents. Nanny and Poppy lived just around the corner from us when Justin was born and almost every evening that his dad was working, Poppy would come over to pick us up to take us to their house for dinner. It was on a regular basis, at about 4 pm that he would come over to get us. All my life I grew up going around that corner to Nanny and Poppy’s house. My Dad would drop me off several mornings on his way to work. He would pick up Poppy and they would go to work while I would go in with Nanny and crawl into bed with her to snuggle another hour or two. When we would get up, she would make me whatever I wanted for breakfast.

Nanny's Raisin Filled Cookies

I looked forward to an egg fried in real butter and toast on those morning with her. Her house was the only place I wanted to eat an egg. They didn’t taste anywhere near as good anywhere else. I was so lucky to have her in my life, and she is the reason I love to bake and feed others.  Or, as some people would say, offer to feed them over and over until they accepted. 🙂 I remember making cookies with her at her home, these raisin filled cookies being one that we would make.

Nanny's Raisin Filled Cookies

All of her grand children knew where to look to find her cookies! She would store them in a Tupperware container in the bottom cupboard just to the right of the kitchen sink. If the box happened to be about empty, she would tell us to go to the big chest freezer in the back entry and get another box of cookies she would have in there. Cookies were abundant at Nanny’s house!

Nanny's Raisin Filled Cookies

As an adult, after I separated from my first husband, I moved into the house just across the road from where I grew up and I was back around the corner from Nanny. Poppy had passed by then and Nanny and I still spent a lot of time together.  I would go over there for dinner or she would come over to my place. Many mornings I would get out of bed, hop in my car still wearing my pajamas and drive over to her house for coffee. Needless to say, a large piece of my heart went with Nanny when she passed. There isn’t a day that goes by that I don’t think of or remember her or something that she said to me. Some of her most remembered remarks are “Shelby Mae, would you like a little bit of something sweet?”, or “I’ll take a little piece of each please” (referring to dessert of course!)

Nanny's Raisin Filled Cookies

If you are lucky enough to still have any of your grandparents around, be sure to share some love with them today and let them know you are thinking of them. I really wish I could do that myself today.

Dedicated today with a heart full of love to all my grandparents.

Archie Whitton Sr. and Mae Iris (Clark) Whitton

Herbert Law and Doris (Hogle) Law

Several other Sunday Supper family members are bringing you heirloom recipes from their grandparents today also. Linked up at the end of this post, these are some recipes you will not want to miss!

Nannys Raisin Filled Cookies

Nanny's Raisin Filled Cookies

This is Nanny's recipe. My only changes are the butter (she used margarine) and rum (she used water). For decorating purposes (frosting not needed) I made some butter rum frosting and glazed a few of them. I will include the frosting recipe but you do not need it on these cookies 🙂
5 from 6 votes
Print Pin Rate
Course: Cookie Recipes, Desserts
Cuisine: American
Keyword: cookie recipe, filled cookies, Raisin Filled Cookies
Prep Time: 20 minutes
Cook Time: 20 minutes
Total Time: 40 minutes
Servings: 36
Calories: 220kcal


For the cookies:

  • 3/4 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 cup light brown sugar
  • 3 large eggs
  • 1-1/2 teaspoon vanilla extract
  • 1 teaspoon baking soda
  • 4 teaspoons baking powder
  • 1/2 teaspoon salt
  • 6-1/2 cups all-purpose flour
  • 3/4 cup sour milk

For the Filling:

  • 1 cup applesauce
  • 1 cup raisins
  • 1/2 cup brown sugar
  • 1/4 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 1-1/2 ounce Captain Morgan's Spiced Rum


  • To make the filling;
  • in a medium-sized saucepan, stir together all filling ingredients and bring to a boil. Immediately turn heat down to a slow simmer and simmer for 20-30 minutes until mixture has thickened and raisins have plumped. Set aside to cool until needed in recipe below.

To make the cookie dough:

  • In a large mixing bowl, mix together butter and sugars until creamy. Add eggs, one at a time and mix until well blended after each addition. Stir in vanilla extract.
  • Mix together dry ingredients and add to wet mixture 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 1/2 cup of flour into the dough.
  • Divide dough into quarters and roll out to about 1/8 inch thickness. Cut two cookie rounds out for each cookie. Place a piece of parchment paper on top of cookie sheet. Place 1 cookie 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 in 350 oven for 17-20 minutes or until lightly golden brown. Cool on cookie rack.

To make the frosting:

  • Mix the butter, sugar and rum together and stir until well combined. You do not want a thick glaze so 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.


The frosting recipe does not make enough to frost all of the cookies. If you want to do this, please double your ingredients. I tend to only frost a portion of my cookies for this recipe.


Serving: 1cookie | Calories: 220kcal | Carbohydrates: 38g | Protein: 3g | Fat: 5g | Saturated Fat: 3g | Polyunsaturated Fat: 2g | Cholesterol: 28mg | Sodium: 133mg | Fiber: 1g | Sugar: 20g


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About the Author: Shelby Law Ruttan

Shelby is the author/owner of Grumpy's Honeybunch. Established in 2007, she shares and preserves family recipes as well as recipes for cooking light and keto. She is an experienced, self-taught home cook who loves to share recipes with others. You can see her work on websites such as Veal Made Easy, Parade, Community Table, SoFab Food, Yummly, and FoodGawker.


  1. claudia September 13, 2015 at 7:06 am - Reply

    These sound so good Shelby can’t wait to try them I love that filling with Morgan in it! WOW!

  2. Stacy September 13, 2015 at 7:10 am - Reply

    You brought tears to my eyes, Shelby. What a sweet post and delightful cookies!

  3. Portuguese Stove Top Pork Roast September 13, 2015 at 8:24 am - Reply

    […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  4. Wendy, A Day in the Life on the Farm September 13, 2015 at 8:27 am - Reply

    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.

  5. Healthier Taco Pie | Food Done Light September 13, 2015 at 8:48 am - Reply

    […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  6. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  7. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  8. Chocolate Chip Banana Cake #SundaySupper September 13, 2015 at 9:15 am - Reply

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  9. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  10. Susan 30A Eats September 13, 2015 at 9:32 am - Reply

    What a sweet post, and I’m not just talking about the cookies, though I could devour a bakers dozen right now!

  11. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  12. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  13. Summer Peach Cake | Pies and Plots September 13, 2015 at 11:55 am - Reply

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  14. Liz September 13, 2015 at 1:26 pm - Reply

    Oh, what sweet memories! And your cookies look like the perfect autumn treat!

  15. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  16. Sarah | Curious Cuisiniere September 13, 2015 at 3:22 pm - Reply

    These sound amazing! They’re going on my Christmas cookie list for sure!

  17. Laura Dembowski September 13, 2015 at 4:09 pm - Reply

    These cookies sound delightful. I love that you added frosting and those fun sparkles.

  18. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  19. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  20. Wonderful!

  21. cathy branciaroli September 14, 2015 at 8:14 am - Reply

    My grandmother made a raisin bar, not a cookie, and while everyone raves about them, no one remembers how they were made – darn!

  22. Cindys Recipes and Writings September 15, 2015 at 6:13 am - Reply

    Boy Shelby do these ever bring back sweet memories!

  23. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  24. Caroline | carolinescooking September 16, 2015 at 8:09 pm - Reply

    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!

  25. Lauren @ Sew You Think You Can Cook September 17, 2015 at 10:33 pm - Reply

    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

  26. Cheryl November 24, 2015 at 5:23 pm - Reply

    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 November 24, 2015 at 7:47 pm - Reply

      Hi Cheryl, I hope you enjoy the cookies! My mom used to fold the cookie in half also for turnovers 🙂

  27. Jeri Tachappat November 10, 2016 at 10:38 pm - Reply

    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 November 11, 2016 at 5:10 am - Reply

      Hi Jeri, Thank you 🙂 Yes. I mean milk with vinegar or lemon.

  28. […] Nanny’s Raisin Filled Cookies by Grumpy’s Honeybunch […]

  29. Polly Hastings December 7, 2017 at 4:03 pm - Reply

    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 December 10, 2017 at 7:16 pm - Reply

      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!

  30. Anonymous October 7, 2019 at 5:57 pm - Reply


  31. […] for her cookies, that is certain. And, my favorite cookie of all time that she would make was a Raisin Filled Cookie. However, she also was an excellent pie maker! My favorite pie that she would make was a Pineapple […]

  32. Connieph9 December 21, 2020 at 3:24 pm - Reply

    5 stars
    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 December 22, 2020 at 8:09 am - Reply

      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

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Shelby Welcome! I'm Shelby, author of Grumpy's Honeybunch. I have been sharing family favorite recipes since 2007. I started the Keto Diet in October 2017 and since then I have been creating Keto ... read more

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