Sandwich-cookie recipe passed down through generations

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Heather Penno’s date-filled cookies have a long matrilineal history.

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Hey there, time traveller!
This article was published 08/12/2025 (312 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.

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

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.

MIKAELA MACKENZIE / FREE PRESS

Heather Penno’s great-grandmother made this tender sandwich cookie a Christmas tradition.

Eva Wasney

Eva Wasney
Arts Reporter

Eva Wasney is a reporter for the Winnipeg Free Press.

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