Grandfather’s Favorite Iced Chocolate Cookies

These cookies are my grandfather’s favorite iced chocolate cookies! They are an old family recipe for pillowy soft, cakey cookies iced with a tasty chocolate icing.

Grandfather's Favorite Chocolate Cookies on a blue plate next to a cooling rack

Overhead view of Grandfather's Favorite Chocolate Cookies on a cooling rack

So there’s sort of a non-story story behind these cookies. I’m sure there are actually plenty of memories around them given that they were my grandfather’s favorite, but they aren’t my memories. I never actually met my grandfather. He passed away when my mom was a teenager.

So how do I know they were his favorite?

Well when I was texting my mom several weeks ago to ask her for the cutout sugar cookie recipe we used to make when I was a kid, she got on a kick and started sending me all kinds of cookie recipes and this was one of them. They were actually titled “Jack’s Favorite Chocolate Cookies”. I knew immediately I’d be making them.

Grandfather's Favorite Chocolate Cookies stacked on a plate with a bite out of one
Overhead view of Grandfather's Favorite Chocolate Cookies on a blue plate

I didn’t really know what they’d be like from reading the recipe card. It was typed with a typewriter onto an index card, so there wasn’t exactly a photo. 🙂

Turns out they’re delicious! Not that I really doubted. They are super soft and cakey. They are then topped with an icing made with milk, powdered sugar and melted chocolate. Very simple to make and quite tasty. The icing also gets nice and firm so they actually stack in a container pretty well with parchment paper between them.

I asked my mom about the cookies and my grandfather when she visited this past weekend and she laughed as she remembered how much her father loved the cakey-ness of them and how the icing makes them even more cake-like.

I had so much fun making these and thinking of my grandfather. Though I never met him, I feel like I know a very small part of him after trying his cookies. They might just have to become a Christmas tradition.

Grandfather's Favorite Chocolate Cookies on a cooling rack
Grandfather's Favorite Chocolate Cookies stacked in a bowl

You might also like:

Double Chocolate Cookie Sandwiches
Turtle Chocolate Cookie Cups
Nutella Cheesecake Chocolate Cookie Cups
Reese’s Peanut Butter Chocolate Cookie Sandwiches
German Chocolate Cookie Stacks
XXL Death by Chocolate Cookie

Print
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Grandfather's Favorite Chocolate Cookies on blue plate close up
Recipe

Grandfather’s Favorite Iced Chocolate Cookies

  • Yield: 28-30 Cookies 1x
  • Category: Dessert
  • Method: Oven
  • Cuisine: American

Description

An old family recipe for pillowy soft, cakey cookies iced with a tasty chocolate icing.


Scale

Ingredients

CHOCOLATE COOKIES

  • 1 cup sugar
  • 1/2 cup salted butter, room temperature
  • 1 egg
  • 1/2 cup milk
  • 1 1/4 tsp baking powder
  • 1 1/2 cups flour
  • 3 tbsp cocoa

ICING

  • 2 cups powdered sugar
  • 45 tbsp milk
  • 4 oz chocolate chips, melted

Instructions

1. Preheat oven to 375 degrees.
2. Mix sugar and butter just until combined and smooth.
3. Add egg and milk and mix until smooth.
4. Combine dry ingredients in a separate bowl, then add to wet ingredients. Mix until well combined.
5. Drop heaping tablespoons of cookie dough onto lined cookie sheet.
6. Bake for 8-10 minutes, then remove to cool. Allow cookies to sit on cookie sheet for 2-3 minutes, then remove to cooling rack.
7. Once cookies are baked and cooled, combine powdered sugar and milk for icing. Add the melted chocolate then spread onto cookies.


Enjoy!

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Recipe rating

20 Comments
  1. Nicole

    By mix until smooth, do you mean creaming? Or just stirring? What can I sub for salted butter, if I only have unsalted?

    1. Lindsay

      Not creaming, just until smooth and combined. If you use unsalted butter, you’ll just want to add a pinch of salt.

  2. Virginia

    An other stunning recipe! My family is totally into lifeloveandsugar, despite the sugar rush ????. The outcome of my homebaking with your recipes makes us all very happy. These cake-cookies are one of my daughters favourites.

  3. Colleen

    I am going to try these. My mother used to make a chocolate cookie with a white icing when we were kids. Unfortunately the recipe was lost. I have tried a lot of different recipes but have never found a cookie that tasted like hers. They were pressed cookies but these do look similar. Was wondering if the icing would be ok if I omitted the chocolate. I just found your website and love everything so far – too much to choose from.

    1. Lindsay

      So glad to hear you’re enjoying the site! You can leave out the cocoa. It’ll change the consistency of the frosting a bit, but it should be ok.

  4. Leslee

    Hi Lindsay,
    I may have missed this, but I wondered if you added chocolate sprinkles or chocolate shavings to the top after frosting?  They look delicious and I can’t wait to bake them!

  5. Angela

    I made these cookies to take to my church Christmas party. But once I tasted them they stayed at home and I took another kind to the party! Thanks for posting this and the wonderful story behind the cookies.

  6. Erin R.

    I always love finding out when something is a favorite. It somehow elevates it in my mind, that it must be special it it was XX’s favorite. These do look wonderful, and that frosting with actual melted chocolate is calling to me. Lovely post.

  7. tanya

    Aww, family recipes are the best! today i am making my grandmothers sand trnd tarts with my son. These do look really really good 🙂

  8. Taylor @ Food Faith Fitness

    How sweet to have something that he loved so much, especially when you never got to make an actual face to face connection with him! Connecting through these cookies is priceless in my mind! -These look so so so good and cookies are always better when they are special 🙂

  9. June @ How to Philosophize with Cake

    I can see why these are such a favorite–they look so rich and chocolaty! Love the chocolate frosting 🙂

  10. Mir

    I’m sure your grandfather would be happy to know that you made his favorite. I love how we uncover information about family even as adults, things we didn’t know before. These look very special!

  11. Stephanie

    My grandfather’s name is Jack and he has quite a sweet tooth (especially for all things chocolate) so I think I will have to bake him up a batch of these and send them to him. Sadly, he has Alzheimer’s so he won’t recall me as the sender, but knowing that he will enjoy the cookies will make me very happy.

    Stephanie

  12. Katrina

    These cookies look delicious! Not only do I love the recipes you share but the stories that go with them really give us readers a glimpse of who you are. I love that you love your family the way you do and that family recipes aren’t just recipes, but a way of knowing someone you never had the chance to meet. Especially around the holidays it is so nice to read something so heartfelt 🙂

Lindsay
About Lindsay

I'm a wife and mom to twin boys, a baby girl and a sweet black lab with a serious sweets addiction! Bring on the sugar!

Scripture I’m Loving

“Be joyful in hope, patient in affliction, faithful in prayer.” Romans 12:12