Total TimePrep: 25 min. + chilling Bake: 10 min.
Makesabout 8 dozen
- 1 cup butter, softened
- 3 ounces cream cheese, softened
- 1 cup sugar
- 1 large egg
- 1 tablespoon grated orange zest
- 1 teaspoon vanilla extract
- 3-1/2 cups all-purpose flour
- 1 teaspoon salt
- 1 cup (6 ounces) semisweet chocolate chips
- 3 ounces cream cheese, softened
- 1/2 cup confectioners' sugar
- 1/4 cup orange juice
- In a large bowl, cream the butter, cream cheese and sugar until light and fluffy. Beat in the egg, orange zest and vanilla. Combine flour and salt; gradually add to the creamed mixture and mix well. Cover and chill for 4 hours or until firm.
- Meanwhile, combine all filling ingredients in a small saucepan. Cook and stir over low heat until smooth; set aside to cool.
- On a floured surface, divide dough in half; roll each half into a 12x10-in. rectangle. Spread with filling. Carefully roll up into a tight jelly roll and wrap in waxed paper. Chill overnight.
- Unwrap and cut into 1/4-in. slices. Place 2 in. apart on ungreased baking sheets. Bake at 375° for 8-10 minutes or until lightly browned. Remove to wire racks to cool.
Nutrition Facts2 each: 119 calories, 6g fat (4g saturated fat), 19mg cholesterol, 100mg sodium, 15g carbohydrate (8g sugars, 0 fiber), 2g protein.
Follow along as we show you how to make these fantastic recipes from our archive.
May 8, 2017
A favorite of friends and family!!
Feb 14, 2017
I love these cookies! I made a similar cookie when I was growing up, so making this recipe was quite nostalgic for me. They tasted just as great and were just as fun to make (and to eat!). THese cookies look so pretty on a cookie tray. THey do take some time to make, but I think they are worth it.
Jan 11, 2015
I've made these cookies for the last eight years. My husband and children love them. Each year I have fine tuned how I prepare them----rolling them and cutting them exactly 1/4" as directed. I'm always happy to share the recipe.
Dec 19, 2012
This is the very first pinwheel cookie I have ever made. I followed the recipe right to the T. Wow! I could not believe I actually made these beautiful cookies! Mine turned out almost as pretty as the picture and they were so good! Thank you Paulette. You have me hooked on pinwheels now. I'm searching the web for different fillings. Love these!
Dec 16, 2011
To begin, yes, these cookies taste good. However, they are a PAIN to make. The recipe doesn't indicate how sticky the dough will be (even after ample chilling) and how much flour you will have to knead into it. And after that, the dough will still be very fragile and will rip/tear easily. I would still make these again, but next time, I'll be more prepared for how much work it takes to make these.
Dec 6, 2011
Mine never look as perfectly round and pretty as the TOH picture, but they are fantastic and the first to disappear from a cookie tray!
Dec 1, 2011
just awful. the filling was so runny it got over the dough and made it look dirty. thought it was a typo. choc was all over the cookies. not worth making
Nov 27, 2011
These cookies are a bit messy to make, but absolutely worth the effort! The chocolate-orange flavor comes through so clearly in this soft, pretty cookie. Be warned: guests love them, and they disappear fast off of the cookie tray!
Dec 3, 2010
This is one of my families all time favorites. I have been making these since they first appeared in the Taste of Home magazine. Delicious!
Dec 2, 2010
Yes indeed this recipe needs ALOT of work! I made these cookies about two weeks ago and was never more unsatisfied with the final results as I was with this cookie. In fact, I have the second log in my freezer that will be thrown out today. I found these cookies to have no flavor and chalky tasting while the chocolate feeling is way too sweet.