Yesterday my husband and I made a little bet.  He said it couldn’t possibly snow this early in the season. It’s not even Halloween yet!

I said, “Anything’s possible.”

I won.

It felt more like December than mid-October, with the snow falling in giant flakes outside the kitchen window, and there’s nothing I love to do more when it’s snowing outside in December than to bake holiday cookies.  So I queued up my winter playlist (which includes a few Christmas songs for good measure) and set about baking these fun little Halloween treats. And that’s how I happened to be carving Jack O’Lantens while listening to Christmas music yesterday.

Linzer cookies are so pretty and festive with the jewel-toned jam peeking out of the cut-outs like treasures hidden inside.  For these cookies I used a pumpkin-shaped cookie cutter and cut the faces out by hand – it’s so much easier than carving real Jack O’Lanterns and gives each cookie a personality all his own – but if you have a Jack O’Lantern cookie cutter that exactly matches the size and shape of the cutter you use for the pumpkin bases, that works too.  When cutting by hand, make sure to cut the openings a little larger than you think they need to be because they will close up a little while baking.  As for the recipe, it couldn’t be easier!  I started with a cinnamon cookie dough and kicked up the flavour and crunch a bit by sprinkling the top cookies (the faces) with even more cinnamon sugar, then filled them with apricot jam.  Apricots go so well with cinnamon sugar – a combination I love – but you can fill the cookies with any jam or even pumpkin butter if you like it (Maybe I’m the only person in the world who doesn’t like pumpkin butter??).  It’s up to you!

Cinnamon Sugar Jack O’Lantern Cookies

1 cup (2 sticks) unsalted butter, room temperature
2/3 cups white sugar + 2 TBSP (for the cinnamon sugar)
1 egg
1 1/2 tsp ground cinnamon, divided
1 tsp pure vanilla extract
1/4 tsp baking powder
1/4 tsp salt
2 1/3 cups all-purpose flour (plus more for dusting)
1/2 cup apricot jam (or any jam or pumpkin butter), room temperature

In a small bowl, mix 2 tablespoons of sugar with 1/2 teaspoon of cinnamon.  Set aside.

In a large mixing bowl, beat the butter with the remaining 2/3 cup sugar until fluffy.  Add the egg,  the remaining 1 teaspoon of cinnamon, the vanilla, baking powder and salt. Beat until combined.  Add the flour and stir in, using a wooden spoon, until the dough just comes together.

Divide the dough evenly into two disks.  Wrap the disks in plastic wrap and refrigerate for at least one hour and up to 24 hours.

When ready to bake, preheat the oven to 350 F (180 C).  Line two baking sheets with parchment paper.

On a well-floured surface, roll one of the disks of dough to a thickness that’s slightly under 1/4 of an inch (6mm). Using a pumpkin shaped cutter, cut out the cookies.  In half of the cookies, cut out a Jack O’lantern face with a sharp knife.  These will be the top cookies and the pumpkins without faces will be the bottom cookies.

Place the cookies on the baking sheets.  Using the cinnamon-sugar that you prepared earlier, sprinkle each face generously.  Leave the bottom cookies plain.  Bake, one pan at a time, for 10 minutes, or until the edges of the cookies are just beginning to turn golden.

Allow cookies to cool completely, then spread 1-2 teaspoons of jam on the bottom cookies.  Top with the jack o’lantern cookies. Place in the fridge until the jam has firmed up.