Baking/ Cookies/ Desserts

Chocolate and Vanilla Pinwheel Cookies

One dough-six cookie designs. Festive and visually pleasing, these soft, buttery, shortbread type Chocolate Vanilla Pinwheel Cookies not only taste good, but they look great as well. Make this cookie as eye-catching as you want once you get the hang of how to place the dough before slicing. I’ve given you some great design ideas, now it’s your turn.

Chocolate and Vanilla Pinwheel cookies with various designs.

Ever since I can remember we made these cookies every year for Christmas. The design started out with the typical pinwheel, then graduated to a checkerboard design, then it just went rogue from there. Family members placed bets on what shape they would see over the holidays.

Some recipes have you make the vanilla and the chocolate dough separate, I like to simplify things and make the recipe all vanilla, then separate the dough and add the cocoa to just the one half.

Though this cookie is typically made at Christmas, it has become a family favorite all year round. See more details in the variations section below on the fun ways you can change up this recipe.

Ingredients for Chocolate and Vanilla Pinwheel Cookies

  • Butter: I like to bake with unsalted butter so I can control the amount of salt since brands differ. Be sure to let the butter sit out to bring to room temperature. If you don’t have unsalted butter and use salted, just omit the salt called for in this recipe.
  • Sugar: White granulated sugar adds the right amount of sweetness.
  • Egg: In this recipe I use only the egg yolk. Add at room temperature. You can bring your egg to room temperature quickly by placing in a bowl of warm water for five minutes.
  • Flour: All-purpose flour.
  • Baking Powder: This is an important ingredient to assist in the rise of the cookie. Since this is baking powder and not the more commonly used baking soda, be sure your container has not expired.
  • Salt: Helps bring out the other flavors.
  • Milk: Since we cut back on part of the egg, milk is used to hold the ingredients together. Whole milk, 1%, or 2% will work. You can even use a milk such as almond milk, etc.
  • Vanilla: Use real vanilla extract for the best flavor. Adds that warm, wonderful flavor.
  • Chocolate: Since we mix the chocolate with half of the dough, I opt for the unsweetened chocolate rather than melted semisweet. I also use the powdered cocoa instead of the unsweetened square since the shelf life is longer.

How to Make Chocolate and Vanilla Pinwheel Cookies

  1. Cream butter and sugar.
  2. Beat in egg yolk.
  3. Mix flour, baking powder and salt in another bowl.
  4. Whisk milk and vanilla in small cup.
  5. Alternate wet and dry ingredients until blended.
  6. Divide dough in half.
  7. Remove one tablespoon of dough and add to other half.
  8. Blend in cooled unsweetened chocolate to smaller piece.
  9. Roll both sections with a rolling pin and stack.
  10. Roll dough in a cylinder shape.
  11. Chill dough after covering with plastic wrap.
  12. Remove dough and slice 1/4 inch thick.
  13. Bake and let cool on cookie sheet before removing.

How the Dough for All the Designs Starts

No matter which design you opt for, the dough starts out the same. Because this cookie makes 12-15 cookies depending on how big or small you create them, you can make all your cookies the same design or cut the dough in thirds and make three different designs.

If you are going for variety, I would make your dough, divide and create the chocolate, then cut each flavor block into thirds.

For the Chocolate and Vanilla Pinwheel Design

This of course is the traditional design and we never tire of it! Simply create the vanilla and chocolate dough. Decide if you want your edges to be chocolate or vanilla and plan accordingly when you stack them. The outside color should be on the bottom. Lightly roll again to gently press the doughs together. Roll the dough into a cylinder and cover tightly. If it looks like your circle has some square edges, you are able to correct that now by rolling the dough with the palms of your hands, gently pressing down. The plastic wrap helps keep it together. Chill for a couple hours or overnight.

Chocolate and Vanilla Checkerboard Design

Of all the designs for the chocolate and vanilla cookies, I make the checkerboard pattern the most.

For full instructions on how to achieve this cool looking cookie check out my Checkboard Cookie recipe.

Chocolate and Vanilla Circle Cookies

I love this cookie design because it’s so simple! This is also a great cookie if you want to add some color, just add red or green food coloring to the vanilla. Change the flavor by adding a peppermint extract to either flavor or the entire recipe. Cut your dough in half again, change which flavor becomes the center. Now you have two different looking cookies.

Roll two cylinders. Roll one piece flat into a rectangle that is 1/4 inch thick, making it as tall as your cylinder. From there you will need to check you’ve achieved the correct width by placing your center roll over the rectangle and gently rolling a corner over. This is where your parchment paper is your friend. Your edges should meet only enough to gently press them together to create an invisible seam. Be sure to roll in plastic wrap and chill.

When you cut these you will notice the shape starts to go from a circle to more of an oval as you press the knife down through the dough after multiple slices. That’s okay if you want an oval cookie! I like to rotate my dough as I cut to retain the circle shape.

Geometric Chocolate and Vanilla Cookies

Bet you didn’t know your would be using a bit of math to make some of these cookies! To create this geometric shape, roll your vanilla and chocolate dough into cylinders. The size of each cylinder will actually be the size of the finished circle so for this one I did shorter cylinders so they were wider cookies.

After you roll your cylinders wrap each one and chill. Once you remove them, you will want to stand each one on it’s end and very carefully cut it in half down the length. Then go back and cut each half again. You should end up with four triangles in each flavor.

Take your chocolate and vanilla triangles and alternate them to form your circle.

At this point you can cover with plastic and gently roll to achieve the perfect circle, or form it into more of a square or rectangle by gently pushing four sides down on the cutting board. Chill before slicing into cookies.

Cookie Cutter and Left Over Designs for Chocolate and Vanilla Cookies

Get creative with cookie cookie cutters! Yes, you heard me! Roll your dough flat then cut in strips. You can position your strips to accents certain cookie cutter shapes such as these mittens. These were a bit hit last year.

It happens all the time…you make these cookies and have some leftover dough from squaring up your design. Don’t let that go to waste! Here are some ideas on what I did with the left overs while making these cookies!

Variations for Chocolate and Vanilla Pinwheel Cookies

Flavor: Change the vanilla flavor by adding some peppermint, orange, or strawberry extract.
Nuts: Chop some pecans or walnuts and add them to the chocolate dough.
Embellishment: Use a colored sugar or chocolate jimmies on the top or on sides prior to baking.
Color: If you love these cookies as much as my family does you can use any food coloring with the vanilla dough to adapt them to any holiday or special occasion. I love how the colors play off the deep color of the chocolate.

  • Christmas: If your colors are more traditional then do red and or green. If you decorate a little more contemporary then opt for super light shades of barely-there pink, blues or greens.
  • Valentines Day: Pink or varying shades of red.
  • St. Patrick’s Day: Green of course. The shade doesn’t even need to be dark, even a light green would play off the brown chocolate and look incredible.
  • Easter: Lavender, pink, orange, blue or yellow. It’s especially striking when you do the checkboard pattern and have several colors mixed with the chocolate. For Easter, I like to do the “circle” version, whether you do the border Chocolate and color the vanilla centers. Prior to cutting your slices, push your dough cylinder down slightly with the palms of your hands and create more of an oval shape.
  • Mother’s Day: A soft pink will do, of course.
  • Father’s Day: Keep them natural and definitely do the checkerboard pattern.
  • Forth of July/Memorial Day: Red and blue to the vanilla, then keep some natural. This is where the “checkerboard cookie” pattern shines!
  • Halloween: Orange looks incredible against the chocolate!

Storing the Delicious Chocolate Vanilla Pinwheel Cookie

Let your cookies cool completely before placing in an air tight container. They can sit out on your counter for 7-10 days or freeze up to 2 months.

Chocolate and Vanilla Pinwheel cookies with various designs.

Chocolate and Vanilla Pinwheel Cookies

Festive and visually pleasing, these soft, buttery, Chocolate Vanilla Pinwheel Cookies not only taste good, but look great as well. Make this cookie as eye-catching as you want once you get the hang of how to place the dough before slicing. (Two hours of chill time is included in the total prep time.)
Print Pin Rate
Course: Dessert
Cuisine: American
Keyword: Checkerboard Cookie, Chocolate and Vanilla, Pinwheel Cookie
Prep Time: 2 hours 20 minutes
Cook Time: 10 minutes
Total Time: 2 hours 30 minutes
Servings: 15 cookies
Calories: 134kcal
Author: Sharon Knott


  • ½ cup butter (room temperature)
  • ½ cup granulated sugar
  • 1 egg yolk (room temperature)
  • cup all-purpose flour
  • teaspoon baking powder
  • teaspoon salt
  • 3 tablespoons milk
  • ½ teaspoon vanilla
  • 3 tablespoons cocoa powder + 1 tablespoon oil (or 1 square unsweetened chocolate, melted)


  • Preheat oven to 350° F and line a baking sheet with parchment paper.
  • In a medium bowl, cream butter and sugar until creamy. Make sure your butter is at room temperature.
  • Beat in egg yolk. Place egg in a bowl of warm water to bring to room temperature.
  • In another bowl, mix flour, baking powder and salt.
  • Whisk milk and vanilla in small cup.
  • Alternate wet and dry ingredients until well blended.
  • Divide dough in half. To equal out the quantities of vanilla and chocolate dough, remove two tablespoons of dough from one half and add to other half.

For the Chocolate Dough

  • Mix your 3 tablespoons of cocoa powder and 1 tablespoon of oil in a small bowl. If you have the unsweetened chocolate square you can melt one square which is the equivalent. Since I don't bake often with unsweetened cocoa, I find it easier and more cost effective to keep cocoa powder such as Hershey's on hand as it has a longer shelf life then the squares. If you do buy the squares, I find they store longer in a drawer in the refrigerator.
  • Blend the unsweetened chocolate with smaller half of dough. Once you add the unsweetened chocolate you will have equaled it out again.
  • For pinwheels. Dust the wax/parchment paper and rolling pin with flour and roll each section into 1/4 inch think rectangles.
  • Place chocolate layer over vanilla or visa-versa depending on which one you want as the outer layer of the pinwheel. Using your wax/parchment paper, tightly roll your dough into a cylinder shape.
  • Cover and chill dough for 2 hours or overnight.
  • Remove dough from refrigerator and slice into 1/4 inch slices. Save any end scrapes to press flat into a cookie.
  • Tip: No matter which shape you are making, I like to rotate my dough every couple of cuts as the cutting action tends to pull the shaped dough downwards. This way your squares and circles will stay true.
  • Line a baking sheet with parchment paper and evenly space each cookie. If your shape looks sloppy, just apply slight pressure on opposites sides. They will make 12-15 depending on the thickness of your roll. These cookies should not spread so you can use a half size baking sheet.
  • Bake for 10-12 minutes. Remove these cookies before they get a golden brown. Let cool slightly before you remove them so they don't break. Store in a covered container on the counter.


Serving: 14g | Calories: 134kcal | Carbohydrates: 17g | Protein: 2g | Fat: 7g | Saturated Fat: 4g | Polyunsaturated Fat: 0.3g | Monounsaturated Fat: 2g | Trans Fat: 0.2g | Cholesterol: 30mg | Sodium: 113mg | Potassium: 37mg | Fiber: 1g | Sugar: 7g | Vitamin A: 212IU | Calcium: 34mg | Iron: 1mg

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