Pre-heat oven to 350°, placing rack in the top third of the oven. Spray non-stick spray on Whoopie pan or a parchment lined sheet pan.
Using Artisan Flour Blend
Whisk together Artisan Flour, cocoa, baking soda and salt; set aside. Mix vanilla into buttermilk; set aside. Beat together butter and brown sugar on medium/high speed until light and fluffy (about 3 minutes in a stand mixer and 5 minutes with an electric hand mixer). Add egg and beat until well combined, add half the flour mixture and mix to combine. Add buttermilk, slowly mix together. When combined add the rest of the flour mixture. Mix and scrape down the side of the bowl and mix well again until smooth.
Using Chocolate Cake Mix
Whisk together eggs, oil and water until well mixed. Add the dry mix and stir to combine.
If using parchment on sheet pan: Scoop out dough with 1 to 1 -1/2" scoop (about 2 TBSP), leaving about 2" between scoops for room to spread. Once scooped, with wet hands gently pick up each scoop and form a ball shape. Moisten fingers or palms and press each ball gently to flatten.
If using Whoopie Pan: fill indentations two thirds full (about 2 TBSP). Then press to flatten with moist hands.
Bake in preheated oven 10 to 14 minutes depending on cake size. Cakes are done when they spring back when touched in the center. Place on a rack to cool. Cool pies completely, make filling, then assemble.
Store cakes for up to 3 days in an air tight container with wax paper in-between layers (It is said that day old pies taste better than fresh ones).
In a bowl of a stand or with electric mixer, cream softened butter, powdered sugar, marshmallow cream, and vanilla (and peppermint extract if using). Beat on low until combined, turn up to medium and beat until fluffy and smooth for 2 or 3 minutes. Use frosting within a few hours for best results.
Prepare ahead: If using crushed peppermints to roll on edges, unwrap peppermint candies and crush in a plastic bag to desired size. Place crushed peppermint on a flat plate or pie pan. Set aside.
On a parchment covered sheet pan, lay first Whoopie cake bottom side up. Use a knife or small spatula to spread a 1/4" layer of filling, or use a small pastry bag or plastic bag to pipe the filling. Start in the center and make a spiral circle, round and round until you are all the way to the edge. Top with 2nd Whoopie pie, rounded side up, to create a Whoopie Pie sandwich.
To decorate with cracked peppermint, either place the peppermint pieces into the filling, or run an extra line of filling around the pies at the seam, then roll in cracked peppermint until well coated.
Chef's Note: How to measure out 2 drops of peppermint extract-pour extract into a small spoon, then pour extra back into the bottle, leaving just the 2 drops needed for the filling.
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