Soft, sweet, and beautiful old-fashioned chocolate vanilla pinwheel cookies use a simple sugar cookie dough flavored with vanilla and cacao powder to impress with looks and flavor! Even better, these chocolate swirl cookies are shockingly simple to prepare and make for a perfect addition to potlucks, parties, during the holidays (especially Christmas), and as gifts!

As much as I love a sweet treat, I’m not much of a cookie baker. I’ve shared a few of my tippy-top options, like ooey-gooey vegan chocolate chip cookies and these orange sugar cookies. But generally, you’ll see me digging into quick breads and cakes. So when I tell you that anyone can make and enjoy these chocolate pinwheel cookies, I’m not overstating it! Not only do these swirl sugar cookies look and taste great, but the process is actually surprisingly simple!

All you need is to create a single sugar cookie dough, add cacao to one half, layer to the two, roll (which is easier than it seems), slice, and bake. Okay, there’s quite a bit of chilling time in-between – but that’s a patience game (or you could even decide to make these cookies spread over several days). The chocolate pinwheels really are as simple as that, otherwise!

Plus, this dough is incredibly make-ahead and freezer-friendly. You can chill the prepared dough for several days or store the dough in the freezer for 2 months. Plus, you can store it at several stages (unrolled dough, rolled cookie log, and even sliced cookies). That way, you always have some swirl cookies on hand for whenever the cookie cravings hit!

Best of all, these slice and bake cookies (aka icebox cookies) require just a few simple ingredients – most of which are likely in your kitchen right now! And with several ways to adapt the flavors of your old-fashion pinwheel cookies, these make for a wonderful addition to your Christmas cookie/holiday cookie collection (along with almond pistachio thumbprint cookies and gingerbread)!

The Vanilla Chocolate Pinwheel Cookies Ingredients

• All-purpose flour: I haven’t tried this recipe with any other type of flour.
• Baking powder: this will help leaven the chocolate pinwheel cookies and provide slight lift and better texture.
• Butter: use softened (not melted) unsalted butter. You can use salted in a pinch but should reduce the remaining salt in the recipe.
• Sugar: I recommend using regular white sugar. While it’s possible to use cane sugar or light brown sugar, they’ll affect the color of the vanilla layer, so I avoid it for this recipe.
• Eggs: use medium eggs. It’s best to use them at room temperature, though it doesn’t matter too much if they’re straight from the fridge.
• Salt: this will help enhance the flavors in these chocolate pinwheels.
• Cacao Powder: you can use cacao powder (less refined but slightly more bitter) or cocoa powder for these delicious chocolate vanilla cookies.
• Instant coffee: (optional) While this is technically optional, coffee helps enhance the cacao’s flavor for a richer chocolate flavor.
• Vanilla Extract: I use homemade vanilla extract. Pure vanilla extract is best for the best (and non-artificial) flavor.
• Cinnamon: this is optional, but a large pinch of cinnamon adds extra depth to the chocolate vanilla swirl cookies. At Christmas time, we increase the amount further, and they make for delicious Christmas pinwheel cookies.

Optional Add-ins and Variations

• Extracts: possibly the easiest way to add extra flavor to these old-fashioned pinwheel cookies is with extracts. I like to use options like peppermint, orange, almond, coffee, and coconut to add to the chocolate cookie dough. You’ll likely need ½-1 tsp of extract, but experiment as different flavors will vary.
• Coconut: along with coconut extract, you could also add some shredded coconut to the vanilla dough (or better yet, roll the outside of the cookie dough roll in shredded coconut before slicing and baking).
• Jam-filled: raspberry, strawberry, cherry, and even rose jam all pair well with these vanilla chocolate cookies. To create a jam “filling,” simply spread a thin layer of jam over the top of your stacked cookie dough before rolling it into a log. It’s best to use slightly “tart” jam/jelly since the chocolate swirl cookies are already so sweet.
• Chocolate orange: along with adding orange extract to the chocolate dough, add the zest of one small orange to the vanilla dough.
• Chocolate peppermint pinwheel cookies: add peppermint extract to the chocolate or both doughs and, optionally, roll the cookie dough logs in green and red sprinkles for wonderful Christmas peppermint pinwheel cookies.
• Demerara sugar: you can roll the cookie dough log in demerara sugar for crunchy (delicious) outer edges on the chocolate pinwheel cookies.

How to Make Old-Fashioned Chocolate Pinwheel Cookies?

Step 1: Prepare the Sugar Cookie Dough

First, sift the flour, baking powder, and salt into a large mixing bowl and whisk to combine.

In a separate bowl (or in a stand mixer), add the softened butter and beat until creamy. Then, it’s time to cream the butter – gradually add the sugar, mixing constantly, until the mixture is a pale yellow and light and fluffy, with the sugar fully incorporated.

Next, add the eggs (one at a time) and the vanilla to the creamed butter, mixing well in-between each addition.

Finally, add the flour mixture incrementally, mixing in between, until a dough forms. It shouldn’t be sticky.

Step 2: Divide the Dough

Weigh the biscuit dough and divide it into two even pieces. Wrap one in plastic wrap and return the other half to the mixer/bowl.

Add the cacao powder, instant coffee, and cinnamon (if using) to the dough and mix well until incorporated.

You can optionally chill the dough at this point for at least 30 minutes (up to a day) wrapped in plastic wrap in the refrigerator. However, I find it simpler to roll out into the rectangles first.

Step 3: Shape the Dough and Chill

When rolling out the chocolate and vanilla dough, the aim is to make them into equal-sized dough sheets (so they can be layered and rolled). Here is my preferred method:

Place the first dough ball between two sheets of parchment paper or wax paper and roll into a rectangle that’s as close to 9×14-inches (23x35cm) and ¼-inch (0.6cm) thick. Cut away the excess to make it a neat rectangle (the scraps can make spare marbled chocolate vanilla cookies).

I like to measure the size on the parchment paper first, marking it with a pencil (on the side opposite the dough). That way, you can use it as a guideline while rolling.

Repeat this step with the other dough ball. Then transfer both to the fridge for at least an hour to chill (or for up to a day).

Step 4: Roll the Pinwheel Cookies

It’s time for the fun part! First, decide which (chocolate or vanilla dough) you want to be the outer and inner swirl in the pinwheel cookies. OR, if you can’t decide, you can even do half and half, as I did.

Place the color you want to be the “outer” swirl on the counter first and peel away the top layer of parchment paper. Then, remove the parchment paper from the top of the other sheet and carefully flip it over, placing it on top of the first sheet (lining up the edges of the dough). Then gently roll or press just to make sure the two adhere slightly.

If you want half and half, now you can slice the sheets in half lengthwise and flip one over (so the color on the bottom is now on top).

Now it’s time to gently roll the cookie dough into logs. You can use the parchment paper underneath to lift and help you create the first roll. Roll the first roll tightly to avoid gaps in the cookies.

If the dough cracks while rolling (more likely with the drier chocolate dough), just gently pinch it together and continue rolling. If there are cracks on the outer layer, roll it on the surface a little to smooth out the cracks.

TOP TIP: If you’re rolling a single log, I recommend rolling them from the longer side (for fewer swirls but a nice cookie size). If you roll from the short side, you’ll have tons of swirls and larger cookies – it’s up to you.
If you’re creating two logs (as I did), I like to roll from the short side to create a nice swirl within.

Once rolled, re-wrap the roll/s in parchment paper. Then place back in the fridge to chill for an additional hour (or overnight). Alternatively, chill it in the freezer for 20-30 minutes.

Step 5: Slice and bake the pinwheel cookies

Preheat the oven to 350ºF/175ºC.

Then, remove the roll/s from the fridge. If the underside is slightly flat from resting in the fridge, lightly roll it on the surface to smooth it out. If you chilled the sugar cookie dough in the freezer, allow it a few minutes at room temperature before slicing.

Then slice the log into ¼-inch cookies and place them on a parchment-lined baking sheet, separated by around 1 inch.

Then, place the cookie sheet on the middle shelf in the oven. Bake for between 10-12 minutes, or until the edges are just becoming golden.

It’s best to bake one tray of cookies at a time (so it’s in the middle of the oven). While baking the first back, you can prepare and cut the cookies for the second. Alternatively, you can save the rest for later (read the storage section below for details).

Once baked, remove the cookies from the oven. Allow them to cool on the tray for a few minutes before transferring to a wire rack until fully cooled.

How to Store Chocolate Pinwheels?

Make ahead: there are several ways you can make these old-fashioned pinwheel cookies ahead.

• The mixed dough: wrap it in plastic wrap and store in the fridge for 4-5 days or in the freezer for up to three months.
• The rolled cookie dough log: wrap tightly in plastic wrap and store in the freezer for up to three months. You can also gift the frozen logs to friends and family. That way, they can defrost (15-20 minutes at room temperature) and slice and bake the cookies when wanted.
• The sliced cookies: flash freeze the cookies spread out on a baking sheet (not touching) until solid. Then transfer to a freezer-safe container or Ziplock bag for 3 months.

Store: allow the chocolate pinwheel cookies to cool and then store in an airtight container on the counter for 3-5 days. You can also freeze the baked cookies for up to 3 months. Allow them to thaw on the counter before serving.

FAQs

Recipe Top Tips and Notes

• Don’t skip the chilling: these chocolate swirl cookies are simple to prepare WHEN working with chilled dough. In fact, this recipe requires you to chill the dough at 2 stages. The second is particularly important as the chilled, firm dough allows you to easily slice it without squashing/misshaping the cookies.
• If you struggle to slice the cookies: (even after chilling the dough), you can slice pieces that are thicker and use a rolling pin to flatten them. Just note that they will obviously be larger, less-even shaped cookies, and you’ll be able to make less overall.
• If the dough is sticky: if you’ve added all the flour and the dough is still sticky, I recommend dividing the dough in half. Then add more flour, a teaspoon at a time, to one portion. The “stickier” dough should be the one you add the cacao powder to.
• It’s best to cook in batches: that way, you can use a single tray in the center of your oven, so they cook evenly.
• Rolling the chocolate dough: as this dough is drier, it will be more prone to cracking, especially when chilled. I recommend removing it from the fridge a few minutes before the vanilla dough.
• If the chocolate dough is too dry: if you find the chocolate dough too dry or crumbly when rolling it out, add a little extra liquid to the dough. You can do this with water/milk or even a spoonful of oil. Add it one teaspoon at a time.
• To marble the chocolate vanilla cookies: simply divide the dough and take a ball of both the vanilla and chocolate, roll them together, and flatten. Each of the chocolate vanilla cookies will have a slightly different marble pattern.

More Christmas dessert recipes

• Orange Sugar Cookies (Christmas edition)
• Gingerbread cookies (and mug toppers)
• The ultimate guide to the best Christmas gingerbread house
• White Chocolate Peppermint Bark (+ Multiple Variations | Keto, Vegan Optional)

If you try this old-fashioned chocolate pinwheel cookie recipe, I’d love to hear your thoughts/questions below. Also, I’d appreciate a recipe card rating below, and tag me in your recipe recreations on Instagram @Alphafoodie!