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Mix dry ingredients–flour, baking powder, baking soda, salt, & spices–in a medium bowl until well blended.
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Beat butter & brown sugar on medium-high speed 2-3 minutes, until pale and fluffy, then mix in eggs and beat in well. Add pumpkin, vanilla, & evaporated milk. Beat on medium until well blended.
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Add dry ingredients to wet mixture and beat until blended. Stir in chocolate chips, if desired. Mixture will be runnier than “regular” cookie dough–more like thick cake batter.
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Using cookie scoop, drop uniform balls onto parchment paper-lined cookie sheet. Bake at 375 degrees for 11-14 minutes, until cookies are slightly springy.
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Remove cookies from oven; let cool for a minute or two, then transfer to wire cooling racks before they have a chance to stick to the parchment paper. (Note: The cookies by themselves will be a little on the salty side, which (I think) is the perfect compliment to the sweetness of the icing. However, if you plan to make only the cookies with no icing, you may want to cut the salt to 1 teaspoon and add an additional 1/2 cup of brown sugar.)
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For icing, beat butter & cream cheese at high speed until fluffy, about 2-3 minutes. Mix in maple syrup and beat another minute. Add powdered sugar and beat again until fluffy and smooth.
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To make sandwiches, spread approximately 1 tablespoon icing onto the backside of one cookie, then press 2nd cookie on top of icing. Makes approximately 3 1/2 dozen sandwiches.