Each year, the Star Tribune Holiday Cookie Contest, now in its 21st year, brings several certainties: entrants insisting their grandma's sugar cookie recipe is the best, warming spices and butter will be bought in bulk, and the bakers' stories will make us laugh, tug at our heartstrings and impress us — sometimes all at once. (Be sure to read about this year's winning bakers.) We can also count on a few surprises. This year, it was the number of recipes with pickles as an ingredient (five). While there are no pickles in this year's winning batch, we do have plenty of warming spices, a hint of Aperol, chocolate and a jolt of heat — plus a few surprises.

Happy holidays, and happy baking.

Earl Grey Butter Cookies with Dark Chocolate-Orange Filling

Makes about 22 sandwich cookies.

Note: Use the tea from an Earl Grey tea bag, which is finer than loose-leaf tea. You'll need a piping bag with a 1/2-inch tip (or cut a 1/2-inch hole in the corner of a plastic zip-top bag). This recipe also works with gluten-free flour. Our 2023 winning recipe is from Catie (Seltz Drew) Fesko of Ham Lake, who was inspired by the famous Pepperidge Farm cookie and adapted a recipe from bakedambrosia.com.

For the cookies:

• 1 1/4 c. all-purpose flour

• 1/4 c. plus 1 tbsp. cornstarch

• 3/4 tsp. baking soda

• 1/2 tsp. kosher salt

• 8 tbsp. (1 stick) butter, room temperature

• 1/2 c. powdered sugar

• 1/3 c. granulated sugar

• 1 egg

• 1 tsp. vanilla extract

• 1 tsp. loose Earl Grey tea (see Note)

• 1 tbsp. milk

For the ganache:

• 1 c. (8 oz.) bittersweet or semisweet chocolate chips

• 1/2 c. heavy cream

• Zest of 1 orange (about 2 tsp.)


Preheat oven to 350 degrees. Line 2 baking sheets with parchment paper or silicone mats.

To prepare the cookies: In a medium bowl, whisk together the flour, cornstarch, baking soda and salt. Set aside.

In a stand mixer fitted with a paddle attachment, cream together the butter and both sugars on medium speed until light and fluffy, about 3 minutes. Scrape down the bowl and then add the egg, vanilla and Earl Grey tea, beating to combine.

Beat in the flour mixture on low speed until just combined, then add the milk and beat a few seconds more until incorporated.

Transfer the batter into a large piping bag fitted with a 1/2-inch round tip. Pipe the batter in 2-inch logs onto the prepared baking sheets, spacing each log about 3 inches apart. (See baking tip below.)

Bake the cookies one sheet at a time until lightly golden brown at the edges, about 8 to 10 minutes. Remove from heat and cool completely on a wire rack.

To prepare the ganache: Place the chocolate in a medium bowl. Combine heavy cream and orange zest in a small saucepan. Heat on stove over medium heat until barely simmering.

Add hot cream mixture to bowl with chocolate and let sit for 1 to 2 minutes. Mix with a whisk until the chocolate is melted and the mixture is smooth and glossy. Let ganache cool to room temperature.

Transfer cooled ganache to a piping bag fitted with a 1/2-inch round tip. Pipe the ganache onto the flat side of 1 cookie, then sandwich together with the flat side of another cookie (alternatively, you can spread the ganache onto each cookie with a knife or offset spatula). Repeat until all the cookies have been filled and sandwiched.

Baking tip: To ensure the cookies are a uniform size, use a toothpick as a guide when piping. Alternatively, draw 2-inch lines on parchment paper with a pencil or marker, flip parchment over and use that as your guide.

Ginger Chocolate Bliss

Makes about 35 cookies.

Note: This cookie must be prepared in advance to allow time for the fillings to chill and the cookies to set. From Lori Lippert of St. Paul. Lippert created the Ginger Chocolate Bliss by combining and adapting recipes from seriouseats.com and the 2003 cookbook "Once Upon a Tart," by Frank Mentesana and Jerome Audureau.

For the dough:

• 1 1/2 c. sugar

• 1 c. (2 sticks) cold unsalted butter

• 2 heaping tbsp. unsulfured molasses (not blackstrap)

• 2 1/2 tsp. ground ginger

• 1 tsp. baking soda

• 2 teaspoons Ceylon cinnamon, or 1 tsp. regular ground cinnamon

• 1 tbsp. cocoa powder

• 1 tsp. ground cloves

• 1 tsp. salt

• 2 2/3 c. all-purpose flour

• 4 tbsp. heavy cream

• Coarse-grained white decorating sugar

For the chocolate layer:

• 4 oz. semisweet chocolate chips, melted

For the white chocolate ganache filling:

• 3 tbsp. heavy cream

• 6 oz. white chocolate, finely chopped

• 2 tsp. fresh ginger, grated


To prepare the dough: Adjust the rack to lower-middle position and preheat oven to 350 degrees. Line baking sheets with parchment paper.

In the bowl of a stand mixer fitted with a paddle attachment, combine sugar, butter, molasses, ginger, baking soda, cinnamon, cocoa, cloves and salt. Mix on low until moistened, then increase to medium and cream until soft and light — at least 5 minutes. Reduce speed to low and add flour all at once, then drizzle in cream and mix until fully incorporated.

Divide the dough into 70 even pieces, about 1 rounded teaspoon, or 1/2 ounce, each. (Keeping the size consistent is important in having neat sandwich cookies.) Roll into balls. Roll half of the balls in decorating sugar. Place at least 1 ¼ inch apart on parchment-lined baking sheets. Bake for 10 minutes, until cookies start to brown and the tops crackle on top; they will firm up and flatten as they cool. (Finished cookies will be about 2 1/4 inches in diameter.) Cool to room temperature on the baking sheet.

To prepare the chocolate layer: Melt chocolate in a microwave-safe bowl or double boiler. Spread a thin layer of chocolate on the flat side of each unsugared cookie, 1 teaspoon or less. This is the side of the cookie that was touching the baking sheet. Refrigerate the cookies with chocolate for 30 minutes to set.

To prepare the ganache layer: In a small saucepan, bring cream to a boil. Remove from heat and stir in chopped white chocolate. Cover and let sit for 5 minutes. Add grated ginger. Stir thoroughly until ganache is smooth. Cover and, if necessary, refrigerate until thick enough to spread (about an hour).

To assemble: Pair up your cookie, pairing one sugared half with one chocolate-topped half, matching sizes as close as possible. Use a piping bag or spoon to spread a heaping teaspoon of ganache filling on the chocolate half, leaving about 1/8 inch around the outside edge. Cap with a sugared cookie and squeeze slightly.

If desired, store finished cookies in the refrigerator to keep the fillings firm.

Good Thai Dings

Makes about 36 cookies.

Note: The crystallized ginger should be soft; the recipe calls for 3 to 4 rounds. Tajin is a Mexican chili-lime spice blend; if your store doesn't carry it, look for other brands, such as Red Hot. And Good Life peanut butter can be found at area co-ops. From the mother-daughter baking team of Michelle Laurent of Chanhassen and Grace Laurent of Minneapolis. The pair based the base cookie on a favorite peanut butter cookie recipe clipped from the Taste section decades ago. The candied peanuts, from Sarah Kieffer's book "100 Cookies," are delicious — double or triple the recipe and keep the rest on hand for snacks.

For the candied peanuts:

• 1 c. dry-roasted, salted peanuts

• 1/2 c. granulated sugar

• Pinch of salt, if desired

For the cookies:

• 1 1/4 tbsp. lime zest, from about 3 to 4 limes, finely minced

• 1 1/4 c. granulated sugar

• 1 1/4 c. flour

• 3/4 tsp. baking soda

• 1/2 tsp. baking powder

• 1/2 tsp. salt (sea salt or granulated salt)

• 1/2 c. (1 stick) unsalted butter, softened

• 1 c. chunky-style sugar-free peanut butter, such as Good Life, at room temperature

• 1/4 c. honey

• 3 tbsp. crystallized ginger, finely minced (see Note)

• 1 tsp. fresh ginger, finely minced

• 1 egg, at room temperature

• 1 tbsp. whole milk

• 1 tsp. vanilla extract

• 1 c. peanut butter chips

For the dough coating:

• 4 tsp. Tajin (see Note)

• 1/2 c. reserved sugar with lime zest

• 1/2 c. granulated sugar, or to taste


Prepare the candied peanuts: In large skillet, mix peanuts, sugar and salt over medium-low heat. Stir constantly and cook until the sugar starts to melt, and then turn down the heat to low. Continue to stir until peanuts are lightly caramelized, up to 10 minutes. Remove from heat and continue to stir until peanuts are coated. Pour onto parchment paper and allow to cool.

Once cool, roughly chop and reserve for cookie topping.

Prepare the cookies: In a medium bowl, mix lime zest and granulated sugar together with your fingers, so the juice from the lime zest permeates the sugar. Reserve 1/2 cup for coating sugar, and set the rest aside.

In a large bowl, combine flour, baking soda, baking powder and salt. Set aside.

In a large bowl, beat butter and peanut butter together with a mixer until fluffy. Add honey, 3/4 cup lime sugar, fresh ginger and crystallized ginger and beat until smooth. Add egg and mix well. Add milk and vanilla extract, mix until combined.

Add flour mixture and combine with a spoon or with the mixer on lowest speed. Mix in peanut butter chips by hand or with mixer on lowest speed.

Let dough rest, covered, in the refrigerator for several hours, but preferably overnight, 12 to 24 hours.

To assemble: Preheat oven to 350 degrees, and line baking sheets with parchment paper.

Prepare the sugar mixture by combine Tajin, remaining 1/2 cup reserved lime sugar, and up to 1/2 cup granulated sugar to reach desired spice level.

Roll chilled dough into balls about 1 to 1 1/2 inches (about 2 tablespoons). Roll in the sugar-Tajin mixture. Place on the parchment-lined baking sheets, about 2 inches apart. Press pieces of candied nuts on top of cookie, but do not flatten cookie.

Bake 10 to 12 minutes, and do not overbake. Cookies may seem slightly underdone but they are not. Remove from oven and cool cookies on sheets for 2 to 3 minutes, then transfer to a wire rack to cool completely.

Aperol Sparklers

Makes about 48 cookies.

Note: Find premade sweetened dehydrated orange slices at stores like Trader Joe's; you can also make your own; there are several recipes available online. From Joanne Holtmeier of Edina, who developed it with her favorite cocktail from Italy in mind.

For the cookies:

• 2 c flour

• 1/4 tsp. salt

• 3/4 c. granulated sugar

• 4 tsp. freshly grated orange zest

• 3/4 c. (1 1/2) sticks butter, softened

• 1 egg

• 1/2 tsp. Aperol Italian liqueur

For the glaze:

• 2 tsp. freshly squeezed orange juice

• 2 tsp. Aperol Italian liqueur

• 3/4 to 1 c. powdered sugar

For decoration:

• Pearlized crystal sanding sugar

• Sweetened dehydrated orange segments, optional (see Note)


Preheat oven to 350 degrees. Line baking sheets with parchment.

To prepare the cookie: Combine flour and salt in a medium bowl and set aside.

Combine the sugar and orange zest in a large mixing bowl with your fingers so that the zest permeates the sugar.

Using a mixer, cream the butter and the orange zest-sugar together until light and fluffy. Add the egg along with the Aperol liqueur. Mix until combined. Slowly add the flour mixture until incorporated thoroughly.

Divide the dough in half and place each half onto a sheet of plastic wrap or parchment and shape into logs 2 inches in diameter. Chill the logs in the refrigerator for 30 to 60 minutes. (Tip: When placing dough logs in the fridge, place each log into a paper towel tube that has been cut down the middle. It helps to keep the round shape.)

When firm, slice dough into 1/4-inch slices. Place the slices on a parchment-lined baking sheet and bake for 8 to 10 minutes, or until set and edges are barely beginning to brown. Remove from heat and let cool completely on a wire rack.

To prepare the glaze: Whisk the orange juice, Aperol and powdered sugar into an icing consistency. Adjust sugar and liquid until you get the desired consistency.

Dip tops of cooled cookies in the icing, place on a wire rack, sprinkle with pearlized crystal sanding sugar and place a small sweetened dehydrated orange segment on the side of cookie, if desired. Let icing set before serving or storing.

Nanaimo Bar Thumbprint Cookies

Makes 30 cookies.

Note: This recipe must be prepared in advance to allow at least an hour for the dough to chill. Find Bird's Custard Powder at World Market or online. If custard powder isn't available, substitute vanilla pudding mix (preferably natural or organic). Use boxed graham cracker crumbs or crush 6 graham cracker sheets until finely ground in a food processor, or place crackers in a plastic zip-top bag and crush them with a rolling pin. From Annette Gustafson of Maple Grove, who developed the cookie for this contest, but also entered it into the State Fair — and won a red ribbon.

For the cookies:

• 1 c. all-purpose flour

• 3/4 c. graham-cracker crumbs (see Note)

• 1/3 c. unsweetened cocoa powder

• 1/4 tsp. salt

• 1/2 c. (1 stick) unsalted butter, at room temperature

• 2/3 c. dark brown sugar

• 1 large egg

• 1 tsp. vanilla extract

• 1/3 c. finely chopped walnuts or almonds

• 2/3 c. unsweetened shredded coconut

For the filling:

• 6 tbsp. unsalted butter, at room temperature

• 1 tbsp. plus 1 tsp. heavy cream

• 2 tbsp. custard powder, such as Bird's (see Note)

• 1 1/2 c. powdered sugar

For the drizzle:

• 1/2 c. bittersweet chocolate chips


Line two baking sheets with parchment paper.

To prepare cookies: In a medium bowl, whisk together the flour, graham-cracker crumbs, cocoa powder and salt. Set aside.

Using a stand mixer fitted with the paddle attachment, beat the butter and brown sugar on medium-high speed until light and fluffy, about 3 minutes. Add the egg and vanilla and beat until combined, about 1 minute. Reduce speed to low. Add the flour mixture, then the nuts and coconut and mix until combined.

Scoop the dough into 30 equal portions, then roll into balls, about 1 tablespoon of dough per ball. (A size #60 cookie scoop is helpful.)

Space the balls evenly on the prepared baking sheets, 15 per sheet. Using your thumb or the end of a wooden spoon handle, press an indent into the center of each ball.

Chill the prepared dough balls for 1 hour in the refrigerator. (If space is limited, chill the prepared dough balls on one baking sheet and then divide them on the other baking sheet before baking.)

When ready to bake, preheat oven to 350 degrees.

Bake for 11 to 12 minutes. Remove from the oven and re-press the indentations while the cookies are still warm (the end of a wooden spoon handle works well; the cookies will be hot). Cool on the baking sheet for 10 minutes, then transfer to a wire rack to cool completely before filling.

To prepare filling and drizzle: Using a stand mixer fitted with the paddle attachment, cream butter on medium speed for about 1 minute. Add heavy cream and custard powder and mix until combined. Slowly add the powdered sugar and mix on low until incorporated. Then mix on medium-high until smooth, light and fluffy, 2 to 3 minutes.

Microwave chocolate in bowl at 50% power, stirring occasionally, until melted, about 1 to 2 minutes.

To assemble cookies: Transfer the buttercream to a piping bag fitted with a #3 tip (alternatively, place buttercream in a large plastic zip-top bag and cut off the tip). Fill each cookie indentation with buttercream. Spoon or pipe drizzles of chocolate over each cookie.

Allow chocolate to set in the refrigerator or at room temperature before serving or storing.