Old Fashioned Chocolate Whoopie Pies with Powdered Sugar and Three Fillings

Have you ever had a whoopie pie? Whoopie pies are delightful, fluffy chocolate cake sandwiches filled with sweet filling and are considered to be one of New England's best known comfort foods. Not all whoopie pies are created equal. If you've only tried a greasy cake smothered in plastic wrap or one sitting under glass and hot lights in a bakery I would argue that you've never tasted a whoopie pie. A real whoopie pie is fresh and soft with the right balance between filling and cake.

I had actually forgotten about whoopie pies until I saw this post by Mowielicious. Immediately upon reading the post memories of my grandmother came flooding back to me. Thanks Mowie.







My grandmother was a very good baker and I remember waiting in eager anticipation for her visit. Occasionally she'd pull out of her bag an old-fashioned round tin full of the homemade goodies. Prying the lid off revealed layers of waxed paper with little whoopie pies hiding underneath. Even though they were small, the chocolate smell was intense and they looked huge in my 6 year old hand. I loved eating them with a huge glass of ice cold milk. Last month while unpacking, I came across her old recipe for whoopie pies hand-typed on an index card. (Anyone out there remember typing?)







My grandmother was born shortly after the turn of the century (the last one) and lived to be nearly 100 years old. She lived through not one but two World Wars, raised a family during the Great Depression, saw women earn the right to vote, watched the Civil Rights and Women's Rights movements unfold and witnessed every major innovation from a man landing on the moon to the development of the internet. It makes me wonder what we'll experience in this lifetime.








This recipe for whoopie pies is incredibly simple recipe to make and will surely please both young and old. Written in the 1930's, it's the real deal. Keep in mind, her recipe is made with vegetable shortening. After reading this, however, I opted to use locally made butter as a substitute.

The traditional filling is vanilla but I experimented with about ten different flavors and narrowed it down to three favorites: vanilla, chocolate and raspberry. These flavors tasted the best without altering the essence of how the whoopie pie is supposed to taste. The good news is that these little cakes also freeze and defrost beautifully so you can stock up. And of course, they're best enjoyed while looking at beautiful spring flowers.







Whoopie Pies

Sift into a bowl:
1 3/4 c. flour
3/4 c. good cocoa powder
1/2 tsp. baking powder
1 1/2 tsp. baking soda
1 cup sugar

Add:
1/2 c. butter
1 egg
1 c. milk
1 tsp.vanilla

Mix well. Drop by the tablespoonful onto a silpat. Bake 8-10 minutes at 375. Baking time will vary by oven. Cake is done when it springs back at the touch of your finger or when a tooth pick inserted into the center of the cake comes out clean. Cool on wire rack. Once cool add desired amount of filling between two cakes and dust with powdered sugar.

Vanilla filling:

Beat for 4 minutes:
1/3 c. evaporated milk
1/3 c. softened butter
1/2 c. granulated sugar
1 tsp. vanilla

Add:
1 to 2 c. powdered sugar (depending upon taste) and mix well.
The mixture should be thick and smooth enough for the two cakes to stick not slide together.

Divide the vanilla mixture into three bowls. Let one bowl be vanilla. For chocolate and raspberry, follow the directions below.

Chocolate filling:
In the second bowl of vanilla filling add cocoa powder by the tablespoonful. Mix and taste until desired flavor is achieved.

Raspberry filling:
In the third bowl of vanilla filling add crushed fresh raspberries by the tablespoonful. Mix and taste until desired flavor is achieved. You may need to increase the amount of powdered sugar to maintain consistency since raspberries are wet. You'll only need a handful of raspberries to get the desired taste.

If you've never had a whoopie pie, you'll love them. They're delicious.

Bon Appetit!