Chestnut Thumbprint Cookies

Chestnut Thumbprint Cookies

We don’t need chestnuts roasting on an open fire to know that the holidays have arrived! The chestnut filling in these adorable cookies is brimming with the flavour of nuts, vanilla and the decadent touch of Redpath® Golden Yellow Sugar. Try them tonight - just don’t forget the chocolate drizzle on top.


36 cookies


45 minutes


14 minutes


For the chestnut filling

  • 1 ½ cups (270 g) whole chestnuts (about 20)
  • 1 cup (180 ml) water, plus extra as needed
  • ⅓ cup (72 g) Redpath® Golden Yellow Sugar, packed
  • 1 whole vanilla bean, split and scraped, or 1 tsp (5 ml) vanilla extract
  • 2 tbsp (30 ml) dark rum
  • ¼ tsp (1 g) salt

For the cookie dough

  • 2 cups (250 g) all-purpose flour
  • 1 cup (128 g) cornstarch
  • 1 tsp (6 g) salt
  • ½ tsp (2 g) ground ginger
  • 1 ¼ cups (284 g) unsalted butter, softened
  • ⅔ cup (80 g) Redpath® Icing Sugar
  • 2 tsp (10 ml) vanilla extract

For decorating

  • ½ cup (85 g) dark chocolate chips


For the chestnut filling

Lay a chestnut, flat side-up, in a folded tea towel. Grasp the chestnut firmly and score an “X” through the skin with a sharp paring knife. Repeat with remaining chestnuts.

Place scored chestnuts in a medium pot and cover with 1 inch (2.5 centimetres) of water. Bring to a boil, reduce heat to medium-low and simmer; 7 minutes.

Turn off heat, leaving chestnuts in the hot water. Remove a couple of chestnuts at a time with a slotted spoon and drain on the tea towel. Peel off the outer skin and inner membrane of the chestnut, using the paring knife to help. The tea towel can also be used to gently rub off the inner membrane (if the inner membrane does not come off easily, place the chestnut back in the hot water for a few more minutes).

Place the peeled chestnuts into a medium pot with 1 cup (180 millilitres) water, Redpath® Golden Yellow Sugar, vanilla bean seeds and vanilla bean pod, if using. Set over medium-low heat and bring to a simmer; 20 minutes.

Allow mixture to cool 10 minutes, then remove the vanilla bean pod and transfer to the bowl of a food processor fitted with the metal blade. Add rum, vanilla extract (if using) and salt. Process mixture until smooth, scraping down the sides of the bowl as necessary. If mixture is very thick, add a couple of tablespoons of water to loosen it up.

Place chestnut mixture in a piping bag fitted with a ½ inch (1 centimeter) plain tip, or in a large heavy freezer bag with one corner cut off.

For the cookie dough

Preheat oven to 350°F (180°C). Line 2 baking sheets with parchment paper.

Whisk together the flour, cornstarch, salt and ginger. Set aside.

In a medium bowl, using an electric mixer on medium speed, cream together the butter and Redpath® Icing Sugar for 3 minutes. Beat in vanilla.

Reduce speed to low and add the dry ingredients. Increase speed to medium and beat for 4 minutes.

Roll dough into 1 ½ inch (3.75 centimetre) balls and place on cookie sheets 2 inches (5 centimetres) apart. Flatten balls slightly and use your finger, or the handle of a wooden spoon dipped in flour, to create an indentation about ½ inch (1 centimetre) in diameter.

Bake cookies, rotating sheets halfway through, until light gold around the base; 12 - 14 minutes. Transfer to a rack to cool completely.

To assemble

Once cooled, pipe about 1 teaspoon (8 grams) of chestnut filling into the centre. Smooth tops of filling with a dampened finger.

In a small bowl, melt chocolate chips in the microwave in 10 second increments, stirring in between; until smooth.

Drizzle chocolate over cookies with a spoon or with a small piping bag.

Filled cookies will keep in an airtight container for up to one week.



  • Unbaked cookie dough, wrapped in plastic and placed in a plastic freezer bag, can be frozen for up to 1 month. Unfilled baked cookies can be frozen in an airtight container for up to 1 month, as well.

  • To save time, use peeled, ready-to-eat chestnuts, if possible.