Ingredients
Cookies- 2 cups flour
- 1 ¼ t baking soda
- ½ t cinnamon
- Pinch of salt
- ½ cup butter, brought to room temperature
- 1 cup dark brown sugar
- 1 egg, brought to room temperature
- ½ cup maple syrup (real, not the high fructose fake stuff)
- ½ cup buttermilk
- 2 t vanilla
Filling
- ¼ cup butter, brought to room temperature
- 4 oz. cream cheese, brought to room temperature
- 2 ¼ cups powdered sugar
- 1/3 cup maple syrup (again, the real stuff!)
- 1 ½ t vanilla
Directions
We’ll start with the cookie part first.In a medium bowl, whisk together the dry ingredients: flour, baking soda, cinnamon and salt. Set aside but not far – you’ll need it soon.
In a large bowl add the butter and brown sugar and beat until smooth. Add in the egg, maple syrup, vanilla and buttermilk and beat again until everything is well combined.
Get your dry ingredients bowl and slowly add them to your wet ingredients until everything is just combined.
Line a couple baking sheets with parchment paper and plop the dough onto each sheet, about a tablespoon-full six to a sheet.
Bake at 350 for about 10 minutes or so, or until the edges and bottoms are a nice golden brown.
Take the sheets out of the oven, let the cookies rest on the sheet for a couple of minutes and then transfer them individually to a wire rack to cool completely.
Once the cookies are cool, you can make the filling. As always, don’t add the filling until the cookies are cool, otherwise it will just slide off and no one wants that (except maybe the dog).
The filling is easy – it’s just mixing. Put the butter and cream cheese into a medium or large bowl and mix until creamy. Slowly add in the powdered sugar and continue mixing until smooth. Finally, add in the maple syrup and vanilla and mix some more until everything is well combined.
Get your cookies and pair them up so that you have pairs that are both about the same size, and lay they upside down. Get your filling and either pipe it or just spoon it on (I piped it because I’m trying to get better at piping. Not sure I succeeded.). 
Do this for half the cookies (one of each pair). If you still have filling left over after you’re done piping, just portion that out among the cookies. Or, if your first cookies have too much filling and you ran out before you got to the end, move some filling around until they all have about the same amount of filling.
Get the paired cookie, squish the flat side on top of the filling and you got yourselves some homemade maple whoopie pies!
Depending on how big you make them, this recipe makes about 20-25 delicious pies!! Or just one big one, I guess, if you’re super ambitious.
Ugly Desserts 