Sandwich-cookie recipe passed down through generations
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Hey there, time traveller!
This article was published 08/12/2025 (265 days ago), so information in it may no longer be current.
Heather Penno’s date-filled cookies have a long matrilineal history.
Her great-grandmother made this tender sandwich cookie filled with jammy dates a Christmas tradition and passed the recipe on to her eldest daughter.
“I always remember my grandmother having a dainty tray and this was definitely on it,” Penno says, adding the cookies only ever make an appearance during the holidays.
MIKAELA MACKENZIE / FREE PRESS
Heather Penno’s tender sandwich cookies are a Christmas tradition.
The tradition of seasonal baking and bequeathing has continued, with the recipe passed down to the eldest daughter of each subsequent generation.
“There were probably three generations baking this cookie at the same time for Christmas and when my great-grandmother passed, it was passed on to me,” she says.
As the fourth in line, Penno is looking forward to updating the recipe title to five generation date-filled cookies when it comes time to pass it on to her eldest niece.
Homemade Holidays is an annual Free Press tradition featuring 12 festive desserts published over 12 days in December. Visit winnipegfreepress.com/homemade to find this year’s batch of reader-submitted recipes.
winnipegfreepress.com/evawasney
MIKAELA MACKENZIE / FREE PRESS
These date-filled cookies were a staple of always on Heather Penno’s grandmother’s dainty tray at Christmas
MIKAELA MACKENZIE / FREE PRESS
Heather Penno’s great-grandmother made this tender sandwich cookie a Christmas tradition.
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Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.
Four Generations Date-Filled Cookies
Dough
375 ml (1 1/2 cup) flour
5 ml (1 tsp) baking soda
10 ml (2 tsp) baking powder
375 ml (1 1/2 cup) oatmeal
250 ml (1 cup) brown sugar
180 ml (3/4 cup) cold butter, cubed
30 to 45 ml (2 to 3 tbsp) milk
Filling
250 ml (1 cup) granulated sugar
450 g (1 lb) dates, chopped
7.5 ml (1 1/2 tsp) vanilla
250 ml (1 cup) water
Mix flour, baking soda, baking powder, oatmeal and brown sugar together in a large bowl. Cut in the butter with a fork or pastry cutter, as if making a pie crust. Mix in milk.
Roll out the dough on a lightly floured board, but not too thinly, and cut into circles with a round cookie cutter.
Preheat the oven to 350 F and bake for 10 to 12 minutes. Let cool.
Add the filling ingredients to a pot and cook over medium heat until the sugar is dissolved. Once cooled, spoon the filling between two cookies to form a sandwich.
— Heather Penno
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Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.
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