Sandwich-cookie recipe passed down through generations Homemade Holidays
By: Eva Wasney Posted: 2:00 AM CST Monday, Dec. 8, 2025 Last Modified: 6:19 AM CST Monday, Dec. 8, 2025 Updates

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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.

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.

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

Homemade Holidays is an annual Free Press tradition featuring 12 festive desserts published over 12 days in December. Click here to find this year’s batch of reader-submitted recipes.

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Eva Wasney
Reporter

Eva Wasney covers environmental issues in Manitoba for The Narwhal in partnership with the Winnipeg Free Press. Read more about Eva.

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