Holiday Cookies Reimagined

Writing by Josephine D’Ippolito

Photography by Justin Negard

Be different this holiday season and make these cookies instead

Perhaps it’s the festive magic in the air, or, more likely, the irresistible aromas of vanilla, caramel and cinnamon wafting through our kitchens. Whatever it is, holiday cookies are a cherished tradition unlike any other. Even those who normally avoid sugar seem to discover their sweet tooth come December, and that’s where I shine. For over 30 years, I’ve baked over 1,000 cookies each December in more than 20 varieties.

While it’s easy to reach for (or Google) recipes for popular classics like sugar cookies or gingerbread men, the cookies I’m sharing here aren’t the ones you’d typically search for online. These are decades-old favorites—passed down through handwritten notes, newspaper clippings or shared among friends—each one perfected over time, and I’m excited to share them with you. 

These recipes are organized from the easiest to the more involved, and all—except the pinwheels—are perfect for beginner bakers and children. I personally guarantee that you and your loved ones will devour every last bite.

Cookies and Cream Truffles

These are consistently every kid’s (and some adults’) favorite treat on the plate. Get ready to fight over the last one.

Hands-on time: 20-30 minutes     

Total time: 2 hours    

Makes 40 truffles.

Ingredients

1 lb. Oreo cookies

8 oz. cream cheese, room temperature

½ tsp. vanilla extract

12 oz. milk chocolate chips

12 oz. dark chocolate chips

Directions

1. Using a food processor, grind cookies to a fine powder. With a mixer, blend cookie powder, cream cheese and vanilla extract until thoroughly mixed (there should be no white traces of cream cheese).
2. Roll the mixture into small balls and place on a parchment-lined cookie sheet. For consistency, you can use a #100 size cookie scoop, which will yield 60 balls. Freeze for one hour.
3. Once frozen, line two additional cookie sheets with parchment paper. Place chocolate chips in a microwave-safe glass bowl. Microwave for 40 seconds, then stir. Continue microwaving in 20-second intervals, stirring each time, until the chocolate is fully melted and smooth.
4. Dip each ball into the chocolate and coat thoroughly. With a fork, lift the balls out of the chocolate and let the excess chocolate drip off. Place the coated truffles on a parchment paper-lined cookie sheet. Refrigerate until set.
5. Once set, layer the truffles between parchment paper in an airtight container; the treats will keep for up to two weeks in the refrigerator. 
6. To make ahead, freeze the cookie balls before dipping them in chocolate. They will keep for up to three months. Dip in chocolate before serving. 

Serve at room temperature.

Coconut Macaroons

Every cookie plate needs variety, and this is a perfect, and easy, way to add some coconut to the mix. Plus, the addition of bittersweet chocolate really elevates the look and taste of this simple recipe.

Hands-on time: 20 minutes   

Cooking time: 13-15 minutes   

Total time: 1 hour   

Makes 20 cookies.

Ingredients

3 cups shredded coconut

1 ½ Tbsp. cornstarch

3 egg whites

¾ cup sugar

½ tsp. vanilla extract

4 oz. bittersweet chocolate

Directions

1. Heat oven to 350°F.  
2. Mix coconut, cornstarch, sugar, egg whites and vanilla extract in a heat-proof bowl.  Set the bowl over a pot of boiling water (or use a double boiler). Heat, stirring until the mixture thickens, about four minutes. Remove from heat and set aside.
3. Spoon out macaroons, about a tablespoonful each, and place on a greased or parchment-lined baking sheet. Bake at 350°F for 13–15 minutes, or until lightly golden but still soft and chewy. Remove to a wire rack to cool.
4. Once cooled, place chocolate chips in a microwave-safe glass bowl. Microwave for 40 seconds, then stir. Continue microwaving in 20-second intervals, stirring each time, until the chocolate is fully melted and smooth.
5. Dip the bottoms of the cookies in chocolate, allowing the excess chocolate to drip back into the bowl. Place on a parchment-paper-lined baking sheet in the refrigerator to set.
6. Once set, layer between parchment paper in an airtight container. They will keep for three days at room temperature or up to one week in the refrigerator. 
7. To make ahead, freeze the macaroons before dipping them in chocolate.  They will keep for up to three months. Dip in chocolate before serving. 

Serve at room temperature.

Raspberry Cobbler Bars

These bars are a showstopper with minimal effort! The shortbread base and crumble are buttery and delicious.

Hands-on time: 20 minutes   

Cooking time: 30 minutes   

Total time: 1 hour 

Makes 25 cookies.

Ingredients

2 sticks butter, softened

½ cup granulated sugar

½ tsp. vanilla

2 ½ cups flour

1 tsp. salt

1 cup raspberry preserves

Directions

1. Preheat the oven to 350°F.
2. Line an 8 x 8-inch baking pan with large parchment paper, leaving enough overhang on the sides to easily lift the baked shortbread from the pan later.
3. In a mixing bowl, beat butter at medium speed until light and fluffy. Add the sugar and vanilla extract and continue beating until well combined. Gradually add the flour and salt, beating until the dough comes together. Press the dough evenly into the bottom of the prepared pan. Prick the dough with a fork about 20 times.
4. Bake at 350°F for 30 minutes until lightly golden. Remove from the oven and allow to cool for 10 minutes.
5. Holding on to the parchment paper on two sides, carefully lift the shortbread out of the pan and place it on a cutting surface. With a knife, trim about an inch from two of the sides. Crumble the trimmings into a bowl and set aside.
6. Spread a thick layer of jam onto the shortbread and then sprinkle the reserved crumbs on top. Cut into 25 squares, about 1.25 inches each.
7. Store the squares in an airtight container, layered between parchment paper. They will keep for 3–4 days at room temperature, up to two weeks in the refrigerator, or they can be frozen for up to three months.

Salted Caramel Shortbread Squares

Warning: These cookie bars won’t win any beauty contests, but they’ll steal the hearts of every salted caramel lover in your life. A dear friend shared this recipe years ago, and it’s been a yearly favorite ever since.

Hands-on time: 30 minutes  

Cooking time: 40-45 minutes  

Total time: 2 hours   

Makes 25 cookies.

Ingredients

For the crust:

2 sticks unsalted butter at room temperature

½ cup sugar

½ cup powdered sugar

1 Tbsp. vanilla

2 cups flour

1 tsp. salt

For the filling:

1/2 bag (14 oz.) caramel candies (about 25 individual caramels), unwrapped

2 Tbsp. + 2 tsp. cream

¼ tsp. vanilla

½ Tbsp. coarse salt

Directions

1. Preheat oven to 350°F.
2. Line an 8 x 8-inch baking pan with large parchment paper, leaving enough overhang on the sides to easily lift the baked shortbread from the pan later.
3. To make the crust: In a large bowl, combine the butter and sugars. Using a mixer on medium speed, beat them together until creamy. Add the vanilla and beat until combined. Add the flour and salt and beat on low speed until a smooth, soft dough forms.
4. Press one-half of the dough evenly into the pan to form a bottom crust. Wrap the remaining dough in plastic wrap and chill in the refrigerator.
5. Bake the crust until firm and the edges are a pale golden brown, approximately 16-18 minutes. Remove the pan from the oven and let it cool for about 15 minutes.
6. While the crust is cooling, make the caramel filling. Place the unwrapped caramels in a microwave-safe bowl. Add the cream. Microwave on high for 40 seconds. Remove from the microwave and stir until smooth. If caramels are not completely melted, microwave on high for 20-second intervals, stirring after each interval, until smooth.
7. Once the caramel is melted, add the vanilla and stir until combined.
8. Pour the caramel filling over the crust. Sprinkle the salt on the caramel.
9. Remove the remaining chilled dough from the refrigerator and crumble it evenly over the caramel.
10. Return the pan to the oven and bake until the filling is bubbly and the crumbled shortbread topping is firm and lightly golden, about 25 minutes.
11. Let cool in pan for at least 30 minutes. Holding the parchment paper on two sides, carefully lift the shortbread out of the pan and place on a cutting surface. With a serrated knife, cut into 25 squares, each about 1.25 inches.
12. Store in an airtight container, layered between parchment paper. They will keep for 3–4 days at room temperature, up to two weeks in the refrigerator, or they can be frozen for up to three months.

Cinnamon Sugar Pinwheel Cookies

Ideal for seasoned bakers, these pinwheel cookies impress with their striking design and crowd-pleasing cinnamon-sugar flavor. Plus, this recipe includes a great hack to keep your counters clean—roll the dough between plastic wrap! 

Hands-on time: 45 minutes  

Cooking time: 12-14 minutes  

Total time: 3 hours

Makes about 60 cookies.

Ingredients

2 sticks butter, room temperature

8 oz. cream cheese, room temperature

2 ½ cups all-purpose flour

½ tsp. salt

½ cup sugar

1 Tbsp. cinnamon

3 Tbsp. melted butter

 Directions

1. In the bowl of a stand mixer fitted with the paddle attachment, beat the butter and cream cheese until well mixed, about two minutes. Reduce the speed to low and add in the flour and salt. Mix well to combine, and then turn off the mixer.
2. Place the dough into a piece of plastic wrap and refrigerate for at least one hour, or freeze for 30 minutes.
3. In a small bowl, mix together the cinnamon and sugar.
4. Take the dough out of the refrigerator and place it in between two large pieces of plastic wrap (this saves the mess of rolling with flour). Roll the dough into a large rectangle, making the dough as even as possible. You should be able to get the dough into an 18-inch by 12-inch rectangle.
5. Spread the melted butter evenly over the dough. Sprinkle with the cinnamon sugar mixture.
6. Starting with the long side, roll the dough into a tight log. Brush the last part of the dough with water to seal the log. You should have an 18-inch long log. Wrap in plastic wrap and refrigerate again for one hour or freeze for 30 minutes.
7. Preheat the oven to 400^oF. Remove the log from the refrigerator and cut the log into cookies using a serrated knife, about ¼-⅓-inch thick.
8. Place the cookies on a parchment-lined baking sheet and bake for 12–14 minutes or until just slightly browned. Cool on a wire rack. Store in an airtight container. They will keep for three to four days at room temperature, up to two weeks in the refrigerator, or they can be frozen for up to three months.

Nutty Thumbprints

Every holiday cookie plate should include at least one thumbprint, a nutty cookie and a fruity one. This Swiss army knife of holiday cookies covers all three requirements.

Hands-on time: 30 minutes  

Cooking time: 14 minutes  

Total time: 1 hour  

Makes 20 cookies.

Ingredients

½ cup butter, room temperature

¼ cup light brown sugar

1 large egg, separated

½ tsp. vanilla extract

1 cup all-purpose flour

¼ tsp. salt

1 cup finely chopped pecans (use a food processor)

½ cup apricot or strawberry preserves, blended in the food processor

 Directions

1. Preheat the oven to 350°F. Cover two cookie sheets with parchment paper and set aside.
2. Whisk the egg white in a small bowl. Finely chop the pecans and place in another small bowl.
3. In a large bowl, cream butter and sugar. Then add the egg yolk and vanilla, and mix until light and fluffy, about two minutes. Add flour and salt; mix until well combined.
4. Scoop dough into 1-inch balls. Dip in the egg white, then roll in chopped pecans until coated. Place two inches apart on the prepared cookie sheets.
5. Make an indent in each ball.
6. Bake in the preheated oven for 10 minutes.
7. Remove from the oven, and, using a small spoon, fill each cookie with jam.
8. Bake for another four minutes, then transfer to wire racks to cool completely.
9. Store cookies in an airtight container, layered between parchment paper. They will keep for 3-4 days at room temperature, up to two weeks in the refrigerator, or they can be frozen for up to three months.

This article was published in the November/December 2024 edition of Connect to Northern Westchester.