Name: Best Date Pinwheel Cookies (A Classic Holiday Recipe)
Prep time: 25 min
Cook time: 15 min
Total time: 2 h 40 min
Cuisine: American
Ingredients: 1 cup Unsalted Butter, at room temperature; 2 cups Packed Brown Sugar; 3 Large Eggs, at room temperature; 1 teaspoon Pure Vanilla Extract; 1 teaspoon Ground Cinnamon; ¼ teaspoon Salt; ½ teaspoon Baking Soda; 4½ cups All-Purpose Flour; 8 ounces Dates, pitted and chopped; 1 cup Pecans, finely chopped; ½ cup Water; ½ cup Granulated White Sugar

Jump to Recipe

Is there a cookie that feels more nostalgic or looks more beautiful on a holiday platter than a classic pinwheel? That perfect, mesmerizing swirl of sweet filling wrapped in a tender cookie dough is a true sign of a special occasion. For many, these intricate-looking treats seem like a project reserved for only the most experienced bakers.

But what if I told you that creating these stunning Date Pinwheel Cookies is far easier than you think? This old-fashioned recipe walks you through the simple steps of making a soft, cinnamon-spiced brown sugar dough and a rich, jammy date and pecan filling. This is a classic “icebox cookie,” meaning the dough logs can be made ahead, chilled, and then simply sliced and baked for a fresh, warm treat whenever you desire. Get ready to master a timeless holiday favorite!

Ingredients

This recipe is broken down into two simple components: a soft, rollable cookie dough and a rich, cooked date and nut filling.

Ingredient	Amount/Quantity
For the Brown Sugar Cookie Dough:
Unsalted Butter, at room temperature	1 cup
Packed Brown Sugar	2 cups
Large Eggs, at room temperature	3
Pure Vanilla Extract	1 teaspoon
Ground Cinnamon	1 teaspoon
Salt	¼ teaspoon
Baking Soda	½ teaspoon
All-Purpose Flour	4 ½ cups
For the Date & Pecan Filling:
Dates, pitted and chopped	8 ounces
Pecans, finely chopped	1 cup
Water	½ cup
Granulated White Sugar	½ cup

Timing

The key to perfect pinwheels is patience and chilling time. While the active work is minimal, allowing the dough and logs to chill properly is essential for a clean slice and beautiful swirl.

Preparation Time: 25 minutes
Chilling Time: 2 hours (minimum)
Cooking Time: 15 minutes per batch
Total Time: Approximately 2 hours 40 minutes

Step-by-Step Instructions

Follow these steps to create beautiful, bakery-quality pinwheel cookies that are as fun to make as they are to eat.

Step 1: Make the Cookie Dough

In a large mixing bowl, using an electric mixer, cream the room-temperature butter and packed brown sugar together on medium speed until the mixture is smooth and fluffy, about 2 minutes. Beat in the eggs one at a time, making sure each is fully incorporated before adding the next. Stir in the vanilla extract. In a separate bowl, whisk together the cinnamon, salt, baking soda, and all-purpose flour. With the mixer on low, gradually add the flour mixture to the wet ingredients until a soft dough forms.

Actionable Tip: Don’t overmix after adding the flour! Mix just until the last streaks of flour disappear. This prevents the development of too much gluten, ensuring your cookies are tender, not tough.

Step 2: Chill the Dough

Divide the finished dough into three equal portions. Place each portion onto a large square of waxed paper, form it into a disc, and wrap it tightly. Refrigerate the dough discs until they are firm, which will take about 1 hour.

Actionable Tip: Chilling the dough at this stage is crucial. It makes the soft dough firm enough to roll out easily without sticking to your work surface.

Step 3: Prepare the Date-Nut Filling

While the dough is chilling, make the filling. In a medium saucepan, combine the chopped dates, finely chopped pecans, water, and white sugar. Cook over low-medium heat, stirring frequently, until the mixture thickens into a rich, jam-like paste. This should take about 5 minutes. Remove from the heat and let it cool slightly while you roll out the dough.

Actionable Tip: Stir the mixture constantly as it thickens to prevent the sugar from scorching on the bottom of the pan. The filling is ready when it’s thick enough to hold its shape.

Step 4: Roll, Fill, and Shape the Logs

Take one portion of the chilled dough and place it on a lightly floured surface. Roll it out into a rectangle that is approximately ¼-inch thick. Using an offset spatula, spread one-third of the warm date filling evenly over the dough, leaving a small ½-inch border along one of the long edges. Starting from the other long edge, tightly roll the dough up to form a log. Repeat this process with the remaining two portions of dough and filling.

Actionable Tip: Work quickly while the dough is still cool. If it becomes too soft, it can be difficult to roll. The ½-inch border helps the log seal properly.

Step 5: Chill the Cookie Logs

Wrap each of the three cookie logs tightly in the waxed paper you used earlier, or in plastic wrap. Refrigerate the logs until they are very firm, which will take at least another hour, but can be left overnight.

Actionable Tip: This second chill is the most important step for perfect pinwheels. A very cold, firm log is the secret to getting clean, round slices without squishing the beautiful swirl you created.

Step 6: Preheat and Prepare for Baking

When you are ready to bake, preheat your oven to 350°F (175°C). Lightly grease two large baking sheets or line them with parchment paper for easy cleanup.

Step 7: Slice and Bake the Cookies

Unwrap one of the chilled logs. Using a sharp, serrated knife, cut the log into uniform ¼-inch thick slices. Arrange the cookie slices on your prepared baking sheets, leaving about 1 inch of space between them.

Actionable Tip: To prevent the logs from getting a flat side as you slice, give the log a slight quarter-turn after every few cuts. This helps maintain its round shape.

Step 8: Bake and Cool

Bake in the preheated oven for about 15 minutes, or until the edges are set and lightly golden brown. Let the cookies cool on the baking sheets for a few minutes before transferring them to wire racks to cool completely.

Nutritional Information

This is an estimate for one cookie, based on the recipe yielding approximately 6 dozen cookies. Please note these values are approximate.

Calories: 120 kcal
Protein: 2 g
Carbohydrates: 18 g
Fat: 5 g
Saturated Fat: 2 g
Sugar: 10 g

Healthier Alternatives

While these are a classic treat, you can make a few adjustments for a more modern, wholesome version.

Whole Grains: Substitute up to half of the all-purpose flour with white whole wheat flour for an added boost of fiber and a nuttier taste.
Reduce the Sugar: You can reduce the brown sugar in the dough by up to ½ cup. The date filling is naturally very sweet, so the cookie will still have plenty of flavor.
Nut Variations: Swap the pecans for finely chopped walnuts or almonds. For a nut-free version, you can use an equal amount of rolled oats or shredded coconut in the filling.

Serving Suggestions

These Date Pinwheel Cookies are a stunning addition to any cookie platter and are perfect for holiday gatherings.

Holiday Cookie Box: These cookies are a must-have for any Christmas cookie exchange or holiday gift box. Their beautiful swirl stands out among other classic cookies. If you like these, you might also enjoy our Classic Shortbread Cookies!
Coffee or Tea Companion: The warm cinnamon and rich date flavor make these the perfect cookie to enjoy with a hot cup of coffee, tea, or a spiced chai latte on a chilly afternoon.
Dessert Platter: Arrange them on a platter with fresh fruit and a selection of cheeses for an elegant and easy dessert offering.

Common Mistakes to Avoid

For perfect pinwheels, be sure to avoid these common cookie-making mistakes.

Not Chilling the Dough: Skipping or rushing the chilling steps will result in a dough that’s too soft to roll and logs that are impossible to slice cleanly. Solution: Don’t skip the chill time! It’s essential for the structure of these cookies.
Using a Dull Knife: Trying to slice a cold cookie log with a dull knife will squish the roll and ruin the pinwheel design. Solution: Use a very sharp, thin, serrated knife for the cleanest cuts.
Overbaking the Cookies: These cookies should be soft and chewy, not hard and crispy. Solution: Pull them from the oven when the edges are just set and lightly browned. They will continue to firm up as they cool on the pan.

Storing Tips

One of the best things about icebox cookies is how well they store, both baked and unbaked.

Storing Baked Cookies: Keep the cooled cookies in an airtight container at room temperature for up to one week.
Freezing Baked Cookies: You can also freeze the baked cookies in a freezer-safe container for up to 3 months.
Freezing the Dough Logs: This is the ultimate make-ahead trick! Wrap the unbaked cookie logs tightly in plastic wrap and then in aluminum foil. They can be frozen for up to 3 months. When you’re ready for fresh cookies, simply thaw the log in the refrigerator for an hour, then slice and bake as directed.

Conclusion

This Date Pinwheel Cookies recipe is a wonderful journey into classic, old-fashioned baking. The process of rolling, filling, and slicing creates a cookie that is as beautiful as it is delicious. With its warm spice, rich date and nut filling, and tender brown sugar dough, it’s a timeless treat that deserves a place in your holiday traditions for years to come.

We hope you fall in love with these beautiful swirl cookies! If you try this recipe, please leave a comment and a rating below to let us know how they turned out. We love to see your creations! For more classic cookie recipes, don’t forget to subscribe.

FAQs

Q1. Can I use different kinds of dates?

Yes! Medjool dates are a great choice as they are naturally very soft and sweet, but any variety of pitted dates will work well in the filling. If your dates seem a little dry, you can soak them in hot water for 10 minutes before chopping to soften them up.

Q2. My cookie logs are getting squished when I slice them. What did I do wrong?

If your logs are squishing, they are likely not cold enough. Pop the log back in the freezer for 15-20 minutes to let it firm up again. Also, make sure you are using a very sharp knife and a gentle sawing motion, rather than pressing straight down.

Q3. Can I make this recipe nut-free?

Absolutely. To make the filling nut-free, you can replace the 1 cup of finely chopped pecans with 1 cup of old-fashioned rolled oats, finely chopped dried apricots, or unsweetened shredded coconut for a different but equally delicious texture and flavor.

Q4. Can I make the dough or the logs in advance?

Yes! This is the perfect make-ahead cookie. The dough discs can be refrigerated for up to 3 days. The unbaked logs can be refrigerated for up to a week or frozen for up to 3 months, making it incredibly convenient to have fresh-baked cookies at a moment’s notice.