While trimming the tree this season I was inspired to create an eggnoggy tasty treat.  After a couple of tries this is what I finally came up with.  The recipe is based upon homemade eggnog because I abhor grocery store eggnog.  Though I cannot attest to the results, it seems feasible that purchased eggnog could be used to save a little time.  If you do decide to make your own eggnog it’s best to prepare it along with the eggnog pastry cream a day ahead to allow for proper cooling.

4 cups 2% milk
2 cups whole milk
1 vanilla bean, halved lengthwise and scrapped
2 tablespoons cinnamon chunks or 2 sticks
24 whole cloves
12 egg yolks
1 cup sugar
1/2 cup vanilla sugar (or extra vanilla and sugar)
1 teaspoon freshly grated nutmeg

Combine milk, cloves, vanilla bean, and cinnamon in a saucepan and heat over low for 5 minutes. Slowly bring milk mixture to a boil. In a large bowl, combine egg yolks and sugars. Whisk together until fluffy. Whisk hot milk mixture slowly into the eggs. Pour mixture into saucepan. Cook over medium heat, stirring constantly for 3 minutes, or until thick. Do not allow mixture to boil. Strain to remove spice chunks.  Stir in nutmeg and refrigerate until cooled.

Eggnog Pastry Cream:
1.5 cups each whole milk and eggnog
7 egg yolks
1/4 cup sugar
1/4 cup vanilla sugar
1/4 cup each flour and cornstarch
1/2 teaspoon salt
1/2 teaspoon freshly grated nutmeg
Pinch of Cinnamon
Tiny pinch of Ground Cloves
1 tablespoon vanilla extract

In a medium saucepan over medium-low heat, bring the eggnog and milk to a simmer.

While the mixture is heating, whisk together egg yolks, sugars, flour, cornstarch, nutmeg, and salt in a medium bowl.

Temper the egg mixture by SLOWLY whisking the heated eggnog mixture. Return to the pan and heat over medium-low heat. Bring the mixture to a low boil, and cook, whisking constantly until the mixture is very thick, 5ish minutes. (Be careful not to overcook or the eggs will scramble.)

Strain the mixture through a fine sieve into a bowl and covering with plastic wrap so the wrap is in direct contact with the pastry cream. Refrigerate until chilled. The pastry cream can be refrigerated up to 5 days (which is significant because you will mos def have leftovers).

Brown Sugar Eggnog C(ake)ookies:
1 cup butter
1 cup dark brown sugar, packed
1/2 teaspoon baking powder
1/2 teaspoon baking soda
1 teaspoon freshly grated nutmeg
3/4 teaspoon salt
2 tablespoons dark rum
1 large egg
2 1/2 cups all-purpose flour
1 1/3 cup eggnog

Preheat oven to 350 degrees.  Mix dry ingredients (nutmeg, baking powder and soda, salt, and flour) in a large bowl and set aside.  In a mixer fitted with a paddle attachment cream butter and sugar until light and fluffy.  Add egg and rum, mix until well blended.  Alternating between the flour mixture and eggnog add in three additions each to the butter mixture mixing until well blended after each addition.  Drop by small teaspoonfuls onto greased or silpat(ed) cookie sheet two inches apart.  Bake for 10 minutes, until lightly golden in color.

Eggnog Fluff:
1/2 cup butter
1 1/2 cup powdered sugar
1 teaspoon freshly grated nutmeg
1 7.5 ounce jar marshmallow fluff
1/2 cup eggnog pastry cream
3.5 ounces white chocolate
1 tablespoon dark rum

Begin to slowly melt the white chocolate over lowest heat. It will cease rapidly so use caution. Stir in the eggnog pastry cream and heat until the chocolate is completely melted. Remove from heat and allow to cool while moving onto the next step.

Beat butter with whisk attachment until creamed. Slowly add the powdered sugar and whisk until smooth and fluffy. Add marshmallow fluff, cooled eggnog white chocolate mixture, and rum. Whisk for a few minutes. Refrigerate until the fluff has firmed up a bit, up to an hour, making for easier assembly.

Chocolate Chai Drizzle:
1/4 Cup Heavy Cream–use only 2 tbsp infused cream
1 Chai Tea Bag
3.5 Ounces Fine Bittersweet Chocolate, chopped

Empty contents of teabag into a small sauce pan. Add cream and heat over low heat until hot, but not boiling. Cover and remove from heat and all the tea to steep while the cream cools. Once cooled strain cream to remove the tea. Return pan to low heat (free of any tea debris) add 2 tbsp infused cream and chocolate. Stir constantly until melted. If it begins to cease add a bit more infused cream. Allow to cool until it sets up to a good piping consistency. Fill piping bag with small round tip with the chai chocolate and drizzle over whoopie pies.

Final Assembly of Whoopie Pie:
Place slighly firmed eggnog fluff into a large pastry bag fitted with any tip you prefer, I used some sort of star tip.  Generously pipe fluff onto underside of the cookie and place a similarly shaped and sized cookie on top.  Place in covered container and refrigerate (or place outside if it’s cold out) to allow the filling to set a bit.  Once set drizzle generously with chai chocolate.  Cool again to set chocolate.  Serve once chocolate sets or refrigerate for up to three days for maximum freshness.  They are best if brought to room temperature before serving, 20ish minutes.