Cookies
Is there anything yummier than homemade cookies? The taste, the way they make scent your home with their aroma...yum! I still have wonderful memories of my grandmother bringing over huge batches of her oatmeal cookies and peanut butter cookies - sometimes at the same time - and insisting on sharing them with us over a cup of tea, then regaling us with stories of her childhood.
Here are six cookie recipes to help you through the day, including my grandmother's aforementioned Oatmeal Cookies and Peanut Butter Cookies. There's also a recipe for Chocolate Espresso Oatmeal Cookies and more. Enjoy!
CREAM CHEESE COOKIES
This recipe, from The Food Network, begins, “A triple dose of cream cheese (mixed into the batter, in chunks in the dough and as a glaze on top) makes these pillowy cookies extra tangy. Freezing the cream cheese before stirring it into the dough makes it easier to cut into clean pieces and keeps the chunks from disintegrating when shaping the dough into balls.” Total Time: 3 hr 25 min; Prep: 40 min; Inactive: 1 hr. 30 min; Cook: 1 hr 15 min; Yield: 3 dozen cookies; Level: Easy.
Read more at: http://www.foodnetwork.com/recipes/food-network-kitchens/cream-cheese-cookies.html?oc=linkback
Ingredients
2-3/4 sticks (1 cup plus 6 tablespoons) unsalted butter, at room temperature
1 teaspoon pure vanilla extract or vanilla bean paste
One 8-ounce package cream cheese, 6 ounces at room temperature, 2 ounces frozen
1-1/4 teaspoons kosher salt
4 cups confectioners' sugar, sifted
1 large egg yolk
3-1/2 cups all-purpose flour, plus more for flouring (see Cook's Note)
2 tablespoons whole milk, plus more if needed
Very finely grated lime zest or finely minced cranberries, for garnish, optional
Directions
Position an oven rack in the center of the oven and preheat to 325 degrees F. Line a baking sheet with parchment.
Combine the butter, vanilla, 4 ounces of the room-temperature cream cheese and 1 teaspoon of the salt in a large bowl and beat with an electric mixer on medium speed until creamy, about 1 minute. Add 2 cups of the sugar and beat until pale and fluffy, about 3 minutes. Add the egg yolk and beat until smooth, then add the flour and beat on low until the dough just comes together. Remove the frozen cream cheese from the freezer and chop into 1/4-inch cubes. Add the cubes to the dough, quickly stirring with a rubber spatula to evenly incorporate them into the dough. Refrigerate the dough for 1 hour.
Using a 1-ounce ice cream scoop or 2 tablespoons, scoop 12 portions of dough, roll into balls and transfer to the prepared baking sheet, spacing them evenly apart. Lightly flour the bottom of a 1/2-cup measuring cup and use it to flatten each cookie into a disk about 1/2 inch thick, re-flouring the cup after each cookie.
Bake, rotating the baking sheet halfway through, until the cookies look set but are still pale and barely brown on the bottom, 20 to 24 minutes. Cool the cookies on the baking sheet for 1 minute, then transfer them to a wire rack to cool completely. Repeat with the remaining cookie dough.
Meanwhile, combine the remaining 2 ounces room-temperature cream cheese, 2 cups sugar and 1/4 teaspoon salt in a medium bowl and beat with an electric mixer on low speed until the mixture forms a thick paste. Add the milk and stir slowly until a thick glaze forms.
When the cookies are cool, dip the entire surface of the top of each cookie in the glaze and lift up, letting the excess glaze drip off, then flip the cookie right-side up and onto the cooling rack. If the glaze is too thick, add another teaspoon of milk to loosen it. If using the cranberries or lime zest, sprinkle on top of the cookies while the glaze is still wet. Allow the glaze to set before serving, at least 10 minutes. Store the cookies in a single layer in an airtight container for up to 5 days.
Special equipment: a 1-ounce ice cream scoop, optional
Cook's Note: When measuring flour, we spoon it into a dry measuring cup and level off the excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)
GRANDMA'S PEANUT BUTTER COOKIES
This was one of my grandmother's recipes, along with the oatmeal cookie recipe that follows. You can find them in my e-cookbook, Off The Wall Cooking.
Ingredients
1/2 C butter
1/2 C peanut butter
1/2 C sugar
1 egg, well beaten
1-1/4 C flour
3/4 tsp. soda
1/2 tsp. baking powder
1/4 tsp. salt
Directions
Cream butter and peanut butter together. Add sugar gradually and cream thoroughly. Add egg. Sift flour once before measuring. Sift flour, soda, baking powder and salt together and add to creamed mixture. Chill dough well, then form into balls the size of walnuts. Place balls on lightly greased baking sheet. Flatten with fork dipped in flour, making criss-cross pattern. Bake at 375 degrees for 10-12 minutes.
GRANDMA'S OATMEAL COOKIES
Another one of my grandmother's recipes. When it came to baking, cookies were her specialty. You can also find these in my e-cookbook, Off the Wall Cooking
Ingredients
1 C flour
1 C brown sugar
3 C quick cooking oatmeal (NOT the instant oats!)
1 C butter or margarine
1/4 C boiling water
1-1/2 tsp. baking soda
Directions
Mix flour and brown sugar. Add oatmeal; stir. Melt butter; add to dry ingredients. Mix baking soda into boiling water; add to other ingredients, stirring well. Place batter into loaf pan, lined with aluminum foil and place in freeze for several hours. Slice and bake at 375 degrees for 10 minutes.
Oatmeal Cookie dough, taken from the freezer; showing first cuts before baking
Then cut down the center, like so:
Placed on parchment paper-covered baking sheet, for easier handling
CHOCOLATE ESPRESSO OATMEAL COOKIES
Makes 48 cookies.
From the December 2011 issue of Vegetarian Times, page 75. This begins, “Take chocolate chip cookies to the next level with this espresso-spiked dough that's laced with chewy oats.”
To view this online, click here.
Ingredients
3/4 cup all-purpose flour or oat flour
1/4 cup unsweetened cocoa powder
1/4 tsp. salt
1/2 tsp. baking soda
4 oz. (1 stick) margarine, softened
3/4 cup sugar
1/4 cup cooled espresso or strong coffee
1/2 tsp. vanilla extract
1-1/2 cups oats
1/2 cup mini semisweet chocolate chips
Directions
Whisk together flour, cocoa powder, salt, and baking soda in bowl.
Cream margarine and sugar together with electric mixer in bowl. Beat in espresso and vanilla. Beat in flour mixture 1/2 cup at a time, adding up to 1/2 cup more if necessary to make thick dough. Stir in oats and chocolate chips.
Divide dough in half. Transfer each dough half to large sheet of plastic wrap or wax paper. Use plastic wrap to shape dough into 2 2-inch-diameter logs with plastic wrap or wax paper. Wrap tightly, and chill 2 hours, or overnight.
Preheat oven to 350ºF. Slice dough logs into 1/2-inch-thick slices. Transfer slices to greased or parchment paper–lined baking sheet. Bake 8 to 11 minutes, or until cookies look dry on top. Cool cookies 3 minutes on baking sheet before transferring to wire rack.
nutritional information Per Cookie: Calories: 56; Protein: less than 1 g; Total Fat: 3 g; Saturated Fat: less than 1 g; Carbohydrates: 8 g; Cholesterol: 0 mg; Sodium: 43 mg; Fiber: less than 1 g; Sugar: 4 g; vegan
CHOCOLATE CHIP ICEBOX COOKIES
This comes from Diana Rattray, who writes for The Spruce Eats. She writes, “These icebox cookies are filled with ground chocolate chips. Use a small food processor or chopper to grind or chop the chocolate chips for these cookies. The dough is chilled slightly and then it's rolled into logs and thoroughly chilled until it's very firm. Plant to let the dough logs chill for at least four hours, or leave them in the refrigerator overnight.” Prep Time: 15 minutes; Cook Time: 11 minutes; Total Time: 26 minutes; Yield: About 3 dozen
To view this online, click here.
Ingredients
1 cup butter (8 ounces)
1/2 cup granulated sugar
1/2 cup light brown sugar
2 large eggs
1-1/2 teaspoons vanilla extract
1/4 teaspoon salt
3 cups all-purpose flour, 13-1/2 ounces
1 cup semisweet chocolate chips, ground or finely chopped
Preparation
In large mixing bowl with an electric mixer cream the butter and sugars together until light; add eggs, vanilla and salt and beat until light and fluffy.
With the mixer on low speed, gradually add the flour. Stir in the ground chocolate chips.
Chill the dough for about 30 minutes to 1 hour, or until firm enough to shape.
Divide dough into 2 portions; form each portion into a log and wrap in plastic wrap or waxed paper.
Refrigerate the dough logs for at least 4 hours, or until very firm.
Heat the oven to 350° F (180° C/Gas 4). Line a baking sheet with parchment paper or a silicone baking mat, or lightly grease the pan.
Cut a log into 1/4-inch slices and place on the prepared baking sheet about an inch apart.
Bake for 9 to 12 minutes.
PUMPKIN SWIRL COOKIES
This is from the Food Network, and begins, “Break open these oversized cookies, fragrant with pumpkin and spice, to reveal a soft interior with a beautiful swirl.”
Level: Easy; Total: 4 hr 20 min (includes chilling and cooling times); Active: 55 min; Yield: 12 large cookies
To view this online, click here.
Ingredients
Sugar Cookie Dough:
2-1/2 cups all-purpose flour (see Cook's Note)
1-1/2 teaspoons baking powder
1/2 teaspoon kosher salt
1-1/2 cups granulated sugar
2 sticks unsalted butter, at room temperature
1 large egg, at room temperature
1 teaspoon pure vanilla extract
Pumpkin Cookie Dough:
2-1/2 cups all-purpose flour, plus additional for dusting (see Cook's Note)
2 teaspoons pumpkin pie spice
1 teaspoon ground cinnamon
1 teaspoon baking soda
1/2 teaspoon kosher salt
1-1/4 cups packed dark brown sugar
1-1/2 sticks (12 tablespoons) unsalted butter, at room temperature
1 large egg, at room temperature
1/2 cup pumpkin puree
1 teaspoon pure vanilla extract
Glaze:
2 cups confectioners' sugar
1 teaspoon pumpkin pie spice
1/4 cup milk
Directions
For the sugar cookie dough: Whisk together the flour, baking powder and salt in a medium bowl; set aside.
Beat together the granulated sugar and butter in a stand mixer fitted with the paddle attachment, scraping down the bowl and paddle once, until light and fluffy, about 3 minutes. Add the egg and beat to fully combine. Add the vanilla and beat to combine. Turn off the mixer. Add half of the dry ingredients and turn the mixer to low; beat until incorporated. Scrape down the bowl and paddle, add the remaining dry ingredients and beat on low until just incorporated. Scrape down the bowl and increase the mixer speed to medium low for 1 minute to make sure the dough is well combined.
Transfer the dough to a piece of plastic wrap. Use a rubber spatula to spread and press the dough into a flat rectangle. Add a second piece of plastic wrap on top, and flatten the rectangle using a rolling pin to approximately 8 by 10 inches. Wrap tightly and refrigerate at least 2 hours and up to overnight.
For the pumpkin cookie dough: Whisk together the flour, pumpkin pie spice, cinnamon, baking soda and salt in a medium bowl; set aside.
Beat together the brown sugar and butter in a stand mixer fitted with the paddle attachment, scraping down the bowl and paddle once, until light and fluffy, about 3 minutes. Add the egg and beat to fully combine. Add the pumpkin and vanilla and beat to combine. Turn off the mixer. Add half the dry ingredients and beat on low speed until incorporated. Scrape down the bowl and paddle, then add the remaining dry ingredients and beat on low speed until just incorporated. Scrape down the bowl and beat on medium low for 1 minute to make sure the dough is well combined.
Transfer the dough to a piece of plastic wrap. Use a rubber spatula to spread and press the dough into a flat rectangle. Add a second piece of plastic wrap on top and flatten with a rolling pin to approximately 8 inches by 10 inches. Wrap tightly and refrigerate at least 2 hours and up to overnight.
Preheat the oven to 350 degrees F and line 2 baking sheets with parchment.
Unwrap the pumpkin cookie dough and place on a lightly floured piece of parchment. Lightly flour the top and a rolling pin and roll into a larger rectangle about 10-1/2 by 16 inches (see Cook's Note). Slide the parchment with the dough onto a baking sheet and refrigerate while you repeat the process with the sugar cookie dough. Roll and refrigerate the sugar cookie dough in the same manner.
Use a pastry brush to dust off any excess flour from the top of the pumpkin cookie dough. Using the parchment to help you, flip the pumpkin cookie dough onto the sugar cookie dough, lining up the 2 rectangles as closely as possible. Cut the dough in half crosswise with a very sharp knife or pastry cutter so you now have 2 rectangles that are 10-1/2 by 7 inches. Stack the dough rectangles on top of one another so you now have 4 layers of alternating cookie dough. Cut this stack crosswise into 6 rows, then lengthwise into 4 rows so you end up with a total of 24 squares. Stack one layered square on top of a second one and, using lightly floured hands, gently press the edges together and round into a domed ball. Place on the prepared baking sheet. Repeat with the remaining squares, evenly spacing 6 dough balls on each lined baking sheet.
Bake, rotating the baking sheets halfway through, until the cookies are puffed in the center and golden brown around the edges, 25 to 30 minutes. Let cool on the pans 10 minutes, then transfer to a wire rack set inside a baking sheet to cool completely.
For the glaze: Meanwhile, whisk together the confectioners' sugar with the pumpkin pie spice in a medium bowl. Add the milk and whisk until completely incorporated. Transfer to a quart-sized resealable plastic bag or piping bag. Snip the end and drizzle the cooled cookies with the icing. Let set, about 20 minutes.
Cook’s Note
When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.) The pumpkin dough will be much softer than the sugar cookie dough so you will have to use more flour when rolling out to prevent sticking. Work quickly; if the dough gets too soft or warm, place the whole piece of parchment on a sheet pan and place in the freezer for a few minutes.
Here are six cookie recipes to help you through the day, including my grandmother's aforementioned Oatmeal Cookies and Peanut Butter Cookies. There's also a recipe for Chocolate Espresso Oatmeal Cookies and more. Enjoy!
CREAM CHEESE COOKIES
This recipe, from The Food Network, begins, “A triple dose of cream cheese (mixed into the batter, in chunks in the dough and as a glaze on top) makes these pillowy cookies extra tangy. Freezing the cream cheese before stirring it into the dough makes it easier to cut into clean pieces and keeps the chunks from disintegrating when shaping the dough into balls.” Total Time: 3 hr 25 min; Prep: 40 min; Inactive: 1 hr. 30 min; Cook: 1 hr 15 min; Yield: 3 dozen cookies; Level: Easy.
Read more at: http://www.foodnetwork.com/recipes/food-network-kitchens/cream-cheese-cookies.html?oc=linkback
Ingredients
2-3/4 sticks (1 cup plus 6 tablespoons) unsalted butter, at room temperature
1 teaspoon pure vanilla extract or vanilla bean paste
One 8-ounce package cream cheese, 6 ounces at room temperature, 2 ounces frozen
1-1/4 teaspoons kosher salt
4 cups confectioners' sugar, sifted
1 large egg yolk
3-1/2 cups all-purpose flour, plus more for flouring (see Cook's Note)
2 tablespoons whole milk, plus more if needed
Very finely grated lime zest or finely minced cranberries, for garnish, optional
Directions
Position an oven rack in the center of the oven and preheat to 325 degrees F. Line a baking sheet with parchment.
Combine the butter, vanilla, 4 ounces of the room-temperature cream cheese and 1 teaspoon of the salt in a large bowl and beat with an electric mixer on medium speed until creamy, about 1 minute. Add 2 cups of the sugar and beat until pale and fluffy, about 3 minutes. Add the egg yolk and beat until smooth, then add the flour and beat on low until the dough just comes together. Remove the frozen cream cheese from the freezer and chop into 1/4-inch cubes. Add the cubes to the dough, quickly stirring with a rubber spatula to evenly incorporate them into the dough. Refrigerate the dough for 1 hour.
Using a 1-ounce ice cream scoop or 2 tablespoons, scoop 12 portions of dough, roll into balls and transfer to the prepared baking sheet, spacing them evenly apart. Lightly flour the bottom of a 1/2-cup measuring cup and use it to flatten each cookie into a disk about 1/2 inch thick, re-flouring the cup after each cookie.
Bake, rotating the baking sheet halfway through, until the cookies look set but are still pale and barely brown on the bottom, 20 to 24 minutes. Cool the cookies on the baking sheet for 1 minute, then transfer them to a wire rack to cool completely. Repeat with the remaining cookie dough.
Meanwhile, combine the remaining 2 ounces room-temperature cream cheese, 2 cups sugar and 1/4 teaspoon salt in a medium bowl and beat with an electric mixer on low speed until the mixture forms a thick paste. Add the milk and stir slowly until a thick glaze forms.
When the cookies are cool, dip the entire surface of the top of each cookie in the glaze and lift up, letting the excess glaze drip off, then flip the cookie right-side up and onto the cooling rack. If the glaze is too thick, add another teaspoon of milk to loosen it. If using the cranberries or lime zest, sprinkle on top of the cookies while the glaze is still wet. Allow the glaze to set before serving, at least 10 minutes. Store the cookies in a single layer in an airtight container for up to 5 days.
Special equipment: a 1-ounce ice cream scoop, optional
Cook's Note: When measuring flour, we spoon it into a dry measuring cup and level off the excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)
GRANDMA'S PEANUT BUTTER COOKIES
This was one of my grandmother's recipes, along with the oatmeal cookie recipe that follows. You can find them in my e-cookbook, Off The Wall Cooking.
Ingredients
1/2 C butter
1/2 C peanut butter
1/2 C sugar
1 egg, well beaten
1-1/4 C flour
3/4 tsp. soda
1/2 tsp. baking powder
1/4 tsp. salt
Directions
Cream butter and peanut butter together. Add sugar gradually and cream thoroughly. Add egg. Sift flour once before measuring. Sift flour, soda, baking powder and salt together and add to creamed mixture. Chill dough well, then form into balls the size of walnuts. Place balls on lightly greased baking sheet. Flatten with fork dipped in flour, making criss-cross pattern. Bake at 375 degrees for 10-12 minutes.
GRANDMA'S OATMEAL COOKIES
Another one of my grandmother's recipes. When it came to baking, cookies were her specialty. You can also find these in my e-cookbook, Off the Wall Cooking
Ingredients
1 C flour
1 C brown sugar
3 C quick cooking oatmeal (NOT the instant oats!)
1 C butter or margarine
1/4 C boiling water
1-1/2 tsp. baking soda
Directions
Mix flour and brown sugar. Add oatmeal; stir. Melt butter; add to dry ingredients. Mix baking soda into boiling water; add to other ingredients, stirring well. Place batter into loaf pan, lined with aluminum foil and place in freeze for several hours. Slice and bake at 375 degrees for 10 minutes.
Oatmeal Cookie dough, taken from the freezer; showing first cuts before baking
Then cut down the center, like so:
Placed on parchment paper-covered baking sheet, for easier handling
CHOCOLATE ESPRESSO OATMEAL COOKIES
Makes 48 cookies.
From the December 2011 issue of Vegetarian Times, page 75. This begins, “Take chocolate chip cookies to the next level with this espresso-spiked dough that's laced with chewy oats.”
To view this online, click here.
Ingredients
3/4 cup all-purpose flour or oat flour
1/4 cup unsweetened cocoa powder
1/4 tsp. salt
1/2 tsp. baking soda
4 oz. (1 stick) margarine, softened
3/4 cup sugar
1/4 cup cooled espresso or strong coffee
1/2 tsp. vanilla extract
1-1/2 cups oats
1/2 cup mini semisweet chocolate chips
Directions
Whisk together flour, cocoa powder, salt, and baking soda in bowl.
Cream margarine and sugar together with electric mixer in bowl. Beat in espresso and vanilla. Beat in flour mixture 1/2 cup at a time, adding up to 1/2 cup more if necessary to make thick dough. Stir in oats and chocolate chips.
Divide dough in half. Transfer each dough half to large sheet of plastic wrap or wax paper. Use plastic wrap to shape dough into 2 2-inch-diameter logs with plastic wrap or wax paper. Wrap tightly, and chill 2 hours, or overnight.
Preheat oven to 350ºF. Slice dough logs into 1/2-inch-thick slices. Transfer slices to greased or parchment paper–lined baking sheet. Bake 8 to 11 minutes, or until cookies look dry on top. Cool cookies 3 minutes on baking sheet before transferring to wire rack.
nutritional information Per Cookie: Calories: 56; Protein: less than 1 g; Total Fat: 3 g; Saturated Fat: less than 1 g; Carbohydrates: 8 g; Cholesterol: 0 mg; Sodium: 43 mg; Fiber: less than 1 g; Sugar: 4 g; vegan
CHOCOLATE CHIP ICEBOX COOKIES
This comes from Diana Rattray, who writes for The Spruce Eats. She writes, “These icebox cookies are filled with ground chocolate chips. Use a small food processor or chopper to grind or chop the chocolate chips for these cookies. The dough is chilled slightly and then it's rolled into logs and thoroughly chilled until it's very firm. Plant to let the dough logs chill for at least four hours, or leave them in the refrigerator overnight.” Prep Time: 15 minutes; Cook Time: 11 minutes; Total Time: 26 minutes; Yield: About 3 dozen
To view this online, click here.
Ingredients
1 cup butter (8 ounces)
1/2 cup granulated sugar
1/2 cup light brown sugar
2 large eggs
1-1/2 teaspoons vanilla extract
1/4 teaspoon salt
3 cups all-purpose flour, 13-1/2 ounces
1 cup semisweet chocolate chips, ground or finely chopped
Preparation
In large mixing bowl with an electric mixer cream the butter and sugars together until light; add eggs, vanilla and salt and beat until light and fluffy.
With the mixer on low speed, gradually add the flour. Stir in the ground chocolate chips.
Chill the dough for about 30 minutes to 1 hour, or until firm enough to shape.
Divide dough into 2 portions; form each portion into a log and wrap in plastic wrap or waxed paper.
Refrigerate the dough logs for at least 4 hours, or until very firm.
Heat the oven to 350° F (180° C/Gas 4). Line a baking sheet with parchment paper or a silicone baking mat, or lightly grease the pan.
Cut a log into 1/4-inch slices and place on the prepared baking sheet about an inch apart.
Bake for 9 to 12 minutes.
PUMPKIN SWIRL COOKIES
This is from the Food Network, and begins, “Break open these oversized cookies, fragrant with pumpkin and spice, to reveal a soft interior with a beautiful swirl.”
Level: Easy; Total: 4 hr 20 min (includes chilling and cooling times); Active: 55 min; Yield: 12 large cookies
To view this online, click here.
Ingredients
Sugar Cookie Dough:
2-1/2 cups all-purpose flour (see Cook's Note)
1-1/2 teaspoons baking powder
1/2 teaspoon kosher salt
1-1/2 cups granulated sugar
2 sticks unsalted butter, at room temperature
1 large egg, at room temperature
1 teaspoon pure vanilla extract
Pumpkin Cookie Dough:
2-1/2 cups all-purpose flour, plus additional for dusting (see Cook's Note)
2 teaspoons pumpkin pie spice
1 teaspoon ground cinnamon
1 teaspoon baking soda
1/2 teaspoon kosher salt
1-1/4 cups packed dark brown sugar
1-1/2 sticks (12 tablespoons) unsalted butter, at room temperature
1 large egg, at room temperature
1/2 cup pumpkin puree
1 teaspoon pure vanilla extract
Glaze:
2 cups confectioners' sugar
1 teaspoon pumpkin pie spice
1/4 cup milk
Directions
For the sugar cookie dough: Whisk together the flour, baking powder and salt in a medium bowl; set aside.
Beat together the granulated sugar and butter in a stand mixer fitted with the paddle attachment, scraping down the bowl and paddle once, until light and fluffy, about 3 minutes. Add the egg and beat to fully combine. Add the vanilla and beat to combine. Turn off the mixer. Add half of the dry ingredients and turn the mixer to low; beat until incorporated. Scrape down the bowl and paddle, add the remaining dry ingredients and beat on low until just incorporated. Scrape down the bowl and increase the mixer speed to medium low for 1 minute to make sure the dough is well combined.
Transfer the dough to a piece of plastic wrap. Use a rubber spatula to spread and press the dough into a flat rectangle. Add a second piece of plastic wrap on top, and flatten the rectangle using a rolling pin to approximately 8 by 10 inches. Wrap tightly and refrigerate at least 2 hours and up to overnight.
For the pumpkin cookie dough: Whisk together the flour, pumpkin pie spice, cinnamon, baking soda and salt in a medium bowl; set aside.
Beat together the brown sugar and butter in a stand mixer fitted with the paddle attachment, scraping down the bowl and paddle once, until light and fluffy, about 3 minutes. Add the egg and beat to fully combine. Add the pumpkin and vanilla and beat to combine. Turn off the mixer. Add half the dry ingredients and beat on low speed until incorporated. Scrape down the bowl and paddle, then add the remaining dry ingredients and beat on low speed until just incorporated. Scrape down the bowl and beat on medium low for 1 minute to make sure the dough is well combined.
Transfer the dough to a piece of plastic wrap. Use a rubber spatula to spread and press the dough into a flat rectangle. Add a second piece of plastic wrap on top and flatten with a rolling pin to approximately 8 inches by 10 inches. Wrap tightly and refrigerate at least 2 hours and up to overnight.
Preheat the oven to 350 degrees F and line 2 baking sheets with parchment.
Unwrap the pumpkin cookie dough and place on a lightly floured piece of parchment. Lightly flour the top and a rolling pin and roll into a larger rectangle about 10-1/2 by 16 inches (see Cook's Note). Slide the parchment with the dough onto a baking sheet and refrigerate while you repeat the process with the sugar cookie dough. Roll and refrigerate the sugar cookie dough in the same manner.
Use a pastry brush to dust off any excess flour from the top of the pumpkin cookie dough. Using the parchment to help you, flip the pumpkin cookie dough onto the sugar cookie dough, lining up the 2 rectangles as closely as possible. Cut the dough in half crosswise with a very sharp knife or pastry cutter so you now have 2 rectangles that are 10-1/2 by 7 inches. Stack the dough rectangles on top of one another so you now have 4 layers of alternating cookie dough. Cut this stack crosswise into 6 rows, then lengthwise into 4 rows so you end up with a total of 24 squares. Stack one layered square on top of a second one and, using lightly floured hands, gently press the edges together and round into a domed ball. Place on the prepared baking sheet. Repeat with the remaining squares, evenly spacing 6 dough balls on each lined baking sheet.
Bake, rotating the baking sheets halfway through, until the cookies are puffed in the center and golden brown around the edges, 25 to 30 minutes. Let cool on the pans 10 minutes, then transfer to a wire rack set inside a baking sheet to cool completely.
For the glaze: Meanwhile, whisk together the confectioners' sugar with the pumpkin pie spice in a medium bowl. Add the milk and whisk until completely incorporated. Transfer to a quart-sized resealable plastic bag or piping bag. Snip the end and drizzle the cooled cookies with the icing. Let set, about 20 minutes.
Cook’s Note
When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.) The pumpkin dough will be much softer than the sugar cookie dough so you will have to use more flour when rolling out to prevent sticking. Work quickly; if the dough gets too soft or warm, place the whole piece of parchment on a sheet pan and place in the freezer for a few minutes.
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