I had my very first whoopie pie about ten years ago when I was in Boston, at a great bakery called Mike's Pastry. I think I was strung out on stress and fatigue from days of college scouting because as my family members and I opened our box of goodies to divvy up our treats of every variety, and someone "accidentally" took my whoopie pie, I threw a fit. Childish, immature, whatever. I had been eyeing that giant, creamy, pillowy, chocolate cakey, long-lost-relative-of-an-Oreo behind the glass with fervent anticipation. Have you ever seen a whoopie pie? A real, traditionally-made, towering sandwich of dark chocolate and cream? Well, if you're a chocolate fiend, like I am, restraint is difficult. Probably because my inner child comes out and I feel like I'm in Willy Wonka & The Chocolate Factory. Flavor comes second to pure aesthetics and your head spins from all the stimuli. "The snozzberries taste like snozzberries!"
Annyyway, I got my pie (with a bite in it!) and it was still amazing—like a taste of heaven. But it was the last time I saw a whoopie pie until now. Whoopie pies are traditionally a New England dessert sometimes called gobs, black-and-whites, or bobs, which I didn't know but makes sense since every time I mention a whoopie pie here in California I get a blank look. Whoopee cushion? Whoopi Goldberg? Making whoopie? Noooo. Well, as I've been in the Halloween spirit lately and wanting to bake something new (and relatively easy), I picked up this month's Everyday Food and decided on some whoopie pie experimentation. They were loads of fun and tasted lovely but after all was said and done, I'd do a few things differently. I'd probably dye the cream a fun orange (or appropriate color for another holiday) instead of sprinkles. And, I'd probably use this recipe because of the rich chocolate cocoa powder and the marshmallow-y filling. That's how I remember it originally and the recipe I used wasn't nearly as impressive on the filling side. But so it goes.
The moist texture of the cakes comes from this secret ingredient: unsweetened applesauce. I'm sure everyone knows this and I'm alone in my bewilderment. I find it really weird but really fun when totally unrelated ingredients are thrown in a recipe. It was a good thing I actually looked at the list of items I needed before shopping at the market because I never would have guessed applesauce. Who buys applesauce? People who have kids or like pork chops. And who bake moist whoopie pies.
The recipe instructs to drop heaping tablespoons of the cake dough about two inches apart. Try to give them ample room because they really expand. And as you drop them onto the baking sheet, aim to make them as round as possible. I made the mistake of having a few oval-shaped cakes that looked like footballs as the end result.
My best advice for these pies is patience. Cool them COMPLETELY before spreading the filling and sandwiching or they'll break apart. Put them in the freezer for 10 minutes or so to harden them a bit.