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Prepare the Classic Shortbread Dough: In a large bowl, cream together the softened salted butter and powdered sugar until light and fluffy. Beat in the vanilla extract. Gradually add the all-purpose flour, mixing until just combined and a soft dough forms. Do not overmix. Divide the dough in half, wrap each half in plastic wrap, and chill for at least 30 minutes.

Prepare the Sandwich Cookie Dough: In a separate large bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy. Beat in the heavy cream. Gradually add the all-purpose flour, mixing until just combined and a soft dough forms. Do not overmix. Divide the dough in half, wrap each half in plastic wrap, and chill for at least 30 minutes.

Prepare the Maraschino Cherry Shortbread Dough: In another large bowl, cream together the softened butter, powdered sugar, and vanilla extract until light and fluffy. Gradually add the all-purpose flour, mixing until just combined. Fold in the chocolate chips and chopped maraschino cherries until evenly distributed. Form the dough into a log (about 2 inches in diameter), wrap tightly in plastic wrap, and chill for at least 30 minutes.

Preheat oven to 325°F (160°C). Line baking sheets with parchment paper.

Bake the Classic Shortbread: On a lightly floured surface, roll out one half of the classic shortbread dough to about 1/4-inch thickness. Cut into desired shapes (rectangles or fingers) and transfer to the prepared baking sheets. Prick the tops with a fork. Repeat with the remaining classic shortbread dough. Bake for 15-18 minutes, or until edges are lightly golden. Let cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Bake the Sandwich Cookies: On a lightly floured surface, roll out one half of the sandwich cookie dough to about 1/8-inch thickness. Cut into small rounds (about 1 1/2 inches in diameter) and transfer to the prepared baking sheets. Repeat with the remaining sandwich cookie dough. Bake for 10-12 minutes, or until edges are set and lightly golden. Let cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Bake the Maraschino Cherry Shortbread: Remove the chilled dough log from the refrigerator. Slice into 1/4-inch thick rounds and place on the prepared baking sheets. Bake for 12-15 minutes, or until edges are lightly golden. Let cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Prepare the Sandwich Cookie Filling: While cookies cool, in a medium bowl, cream together the softened butter, powdered sugar, and vanilla extract until smooth. Beat in the heavy cream until light and fluffy. Divide the filling into two separate bowls. Tint one bowl with a few drops of red food coloring and the other with a few drops of green food coloring, mixing until desired color is achieved.

Assemble Sandwich Cookies: Once the sandwich cookies are completely cool, spread a small amount of red or green filling onto the flat side of one cookie. Top with another cookie, pressing gently to create a sandwich. Repeat with remaining cookies and filling.


Prepare the Classic Shortbread Dough: In a large bowl, cream together the softened salted butter and powdered sugar until light and fluffy. Beat in the vanilla extract. Gradually add the all-purpose flour, mixing until just combined and a soft dough forms. Do not overmix. Divide the dough in half, wrap each half in plastic wrap, and chill for at least 30 minutes.

Prepare the Sandwich Cookie Dough: In a separate large bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy. Beat in the heavy cream. Gradually add the all-purpose flour, mixing until just combined and a soft dough forms. Do not overmix. Divide the dough in half, wrap each half in plastic wrap, and chill for at least 30 minutes.

Prepare the Maraschino Cherry Shortbread Dough: In another large bowl, cream together the softened butter, powdered sugar, and vanilla extract until light and fluffy. Gradually add the all-purpose flour, mixing until just combined. Fold in the chocolate chips and chopped maraschino cherries until evenly distributed. Form the dough into a log (about 2 inches in diameter), wrap tightly in plastic wrap, and chill for at least 30 minutes.

Preheat oven to 325°F (160°C). Line baking sheets with parchment paper.

Bake the Classic Shortbread: On a lightly floured surface, roll out one half of the classic shortbread dough to about 1/4-inch thickness. Cut into desired shapes (rectangles or fingers) and transfer to the prepared baking sheets. Prick the tops with a fork. Repeat with the remaining classic shortbread dough. Bake for 15-18 minutes, or until edges are lightly golden. Let cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Bake the Sandwich Cookies: On a lightly floured surface, roll out one half of the sandwich cookie dough to about 1/8-inch thickness. Cut into small rounds (about 1 1/2 inches in diameter) and transfer to the prepared baking sheets. Repeat with the remaining sandwich cookie dough. Bake for 10-12 minutes, or until edges are set and lightly golden. Let cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Bake the Maraschino Cherry Shortbread: Remove the chilled dough log from the refrigerator. Slice into 1/4-inch thick rounds and place on the prepared baking sheets. Bake for 12-15 minutes, or until edges are lightly golden. Let cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.

Prepare the Sandwich Cookie Filling: While cookies cool, in a medium bowl, cream together the softened butter, powdered sugar, and vanilla extract until smooth. Beat in the heavy cream until light and fluffy. Divide the filling into two separate bowls. Tint one bowl with a few drops of red food coloring and the other with a few drops of green food coloring, mixing until desired color is achieved.

Assemble Sandwich Cookies: Once the sandwich cookies are completely cool, spread a small amount of red or green filling onto the flat side of one cookie. Top with another cookie, pressing gently to create a sandwich. Repeat with remaining cookies and filling.
