These small, melt-in-your-mouth cookies, are both fun to make and to eat. The addition of spice, and pumpkin makes this a softer, denser variation on the clasice shortbread cookies we all love. They are the perfect companions to a warm cup of spiced coffee, or a latte.

Supplies

For the Shortbread:

3/4 cups unsalted butter (room temp)
1/2 cup + 2 tbsp. Icing sugar
1 1/2 cups flour
1/2 tsp salt
2 tsp pumpkin spice
1 1/4 tsp cinnamon
1/4 tsp nutmeg
1/4 tsp cloves
1/4 tsp ginger
1/3 cup pumpkin puree
2 tsp almond, or vanilla extract

For tossing:

1/2 cup Demerara sugar (raw sugar) or Granulated sugar
1 tsp pumpkin spice (see mix above)

Finishing:

1/2 cup semi-sweet chocolate chips, or melts
Coarse salt

Tools:

Mixer (stand mixer, hand mixer, or your hands if you want some biceps)
Spatula
Sieve
Measuring cups and spoons
Cheese cloth
Plastic wrap (optional, you can use parchment paper as well)
Oven, and tray
Parchment paper
Knife

Step 1: Ingredient Prep

The first step in any recipe it to prep the ingredients for baking.

First you will need softened butter, room temp is good but, if you don't have time microwave the stick for 5 seconds flip over and repeat, let stand for a bit. repeat till butter is soft but NOT melted.

Now for the pumpkin, take the 1/3 cup of puree place it in the cheesecloth, and squeeze out the extra liquid.

Sift the icing sugar, and flour. Keep them apart, we want to add them separately.

Mix the pumpkin pie spice, if you're not using a premixed variety.

Step 2: Making the Shortbread Dough

Add softened butter to Mixer, beat until it's nice and fluffy, it should also be much whiter, due to all the air bubbles. This will take 6-8 minutes, scrape down the sides of the mixing bowl.

Now add the icing sugar, mix on low gradually speeding up, mix till smooth.

Scrape down sides of the mixing bowl, and add the pumpkin, almond extract, and the spice blend. mix until smooth

Last add the flour, mix slowly until it's just combined, you don't want to overmix, but make sure there is no dry flour left.

The Dough will seem too dry at first, but soon to will be a soft, slightly sticky, dough.

Step 3: Refrigerating Dough

Place a large square of plastic wrap or parchment paper on a clean counter.

Scrape out the mixing bowl onto the middle of the square.

With your hands shape the dough into a long thin cylinder. Mine was about an inch and a half in diameter. you can make it smaller or larger depending on the size you will want your pumpkins to be.

Roll it up tightly, use the wrap to even out the cylinder. Place it into the fridge, refrigerate for at least 12 hours, ideally 24 to let the spices sink in.

This dough keeps well both in the fridge for about a week, and up to a month or two in the freezer (just be sure to keep it well wrapped in an airtight container.

Step 4: Making the Pumpkins

This step is optional, if you don't feel like taking the time, or you just don't want to, just slice it up into about 1/2-inch rounds and bake as directed.

But it's actually quite easy once you get the feel of it.

Unwrap the cylinder of dough, if you notice that it's gone flat on the bottom just give it a bit of a roll, but it really shouldn't matter since we're going to be shaping it any way.
Use a sharp knife or some unflavored floss to cut the cylinder to you desired width, I went with a bit less then 1/2 of an inch. You can go thicker or thinner if you want, just remember that your baking time will be different as well.
Take two of the rounds, cut one in half, use your finger or the back of the knife to make a slight indent in the cut side.
Now take the second round, and carefully shape it into an oval.
Carefully place both halves of the first round on either side of the oval, gently squeeze them together, if you're worried about them not sticking use your finger dipped in a bit of water to wet the side before sticking together, but you really should have too much of a problem.
Now use the back of the knife, or any utensil really, to indent the top of the middle oval.
For the stem, take a bit of dough, about fingernail sized, I used the end pieces for this. Roll it into a ball, then roll just one end so you have an uneven cylinder, place the thicker end I to the indent. Use your finger to gently smooth out the connecting line.

Now you have a little pumpkin cookie!

Step 5: Tossing the Pumpkins.

Mix together the 1/2 cup of demerara sugar with the tsp. of pumpkin spice, (half of the recipe above)

Use a flat spatula to lift up the cookies and place into the bowl of sugar, carefully flip them over, make sure entire cookie is coated in sugar, then lift out and place onto parchment paper lined baking tray, repeat for all the cookies.

If a cookie comes apart, set it back together on the baking tray, once you bake it will be fine.

Step 6: Baking

Preheat oven to 350*F.

Bake for 15-20 minutes, or until edges are golden brown, baking time will depend on how thick you made the cookie so keep an eye on them.

Once baked let cool down completely.

Step 7: Finishing Touches

Melt the 1/2 cup of chocolate chips, I used the microwave in 10 second bursts, take out the chocolate and stir well in between cycles

Be sure to check the ingredients on the chocolate that your using, if it contains cocoa butter don't heat it over 90*F or you will have to temper it. If you do the easiest way is to stir in un-melted chocolate till the temp goes down.

Dip in the cookie, you do this however you want. I wanted mine to look a bit "muddy" from being in the garden so i dipped in the bottom, when coating cookie in chocolate don't place it straight down go in at an angle so you don't get it on the bottom of the cookie, this will make the chocolate look neater.

While chocolate is still wet, sprinkle on a few grains of coarse salt.

Place cookie onto parchment paper until chocolate hardens.