Pumpkin Whoopie Pies Two Ways

Whoopie pies go seasonal, with pumpkin cookies and two different cream cheese fillings—lemon and maple nutmeg. Recipes below.

Pumpkin Whoopie Pies

WHEN I TOLD MY FRIENDS THAT FOR THIS WEEK’S POST I would be making whoopie pies, no one said, “Making what?”

Pretty much everybody in the United States these days knows what a whoopie pie is. A cookie sandwich with an icing filling, it’s simpler than cake, a happy intermediate between a cupcake and a sweet bread. Whoopie pies emanated from the American Northeast—Maine (where it is the “official state treat”), Pennsylvania and Boston all vow they invented it. Wikipedia reports that the world’s largest whoopie pie was made in South Portland, Maine in 2011. It weighed 1,062 pounds. This is a real thing, that happened.

In the last couple of decades or so, whoopie pies have moved from the humble North Atlantic lunchbox to tables all over the country. They are in hipster bakeries and everywhere on the Internet—hundreds of thousands of recipes and all sorts of flavors. There are Pinterest boards devoted to photos of them. Chocolate, chocolate chip, red velvet, lemon, salted caramel, peanut butter, raspberry, sweet potato… there’s a royal purple one on one pinboard that I am trying to get my head around. But after our recent visit to Syracuse, pumpkin has been on my mind.

This is an adaptation of about 40 online recipes. The recipe can be made in stages—bake the cookies in the morning, then later in the day make the filling and assemble the whole shooting match. Then you will have these convenient treats around for a quick afternoon pick-me-up or informal dessert or on hand when people drop in over the holidays or as part of a game day TV marathon buffet.  Or you could take a batch to the office like I did on Monday or bring it to a holiday pot luck.

After sorting around online for a while, that is what I went with—a classic soft pumpkin cookie, and a cream cheese filling. But we agreed that we wanted more than just cream cheese. This ain’t carrot cake. Terry suggested something to emphasize the tanginess of the cream cheese: lemon. And I proposed something to enhance the warm spicy flavors in the cookie: maple syrup.

The thing about cream cheese filling is that first you mix up the base filling, and after that, you add the flavor. The commitment to a flavoring happens last.  This really cheered me up because I did not have to decide between the two flavors—we could have both.

There are  lots of other fillings you could devise for these simple desserts. Instead of lemon, go for orange or add some bourbon—hard to imagine something that’s not improved by bourbon. Or don’t use filling at all, use a little Nutella. Or use the cookie recipe on its own with a simple fat-free icing—powdered sugar and lemon juice mixed together, then drizzled over the cookies, for instance.

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Pumpkin Whoopie Pies

Whoopie pies go seasonal, with pumpkin cookies and two different cream cheese fillings—lemon and maple nutmeg.
Course Dessert
Servings 15 or 16 3-inch Whoopie Pies

Ingredients

For the cookies:

  • 3 cups flour
  • 2-1/4 cups dark brown sugar (packed—see Kitchen Notes)
  • 1 cup grapeseed or vegetable oil
  • 1 15-ounce can pumpkin puree—not pumpkin pie filling
  • 1 teaspoon cinnamon
  • 1 teaspoon ginger
  • 1/8 teaspoon allspice
  • 1 teaspoon salt
  • 1-1/2 teaspoon vanilla
  • 2 eggs
  • 1 teaspoon baking soda
  • 1 teaspoon baking powder

For the filling:

  • 8 ounces cream cheese at room temperature
  • 4 ounces unsalted butter at room temperature
  • 3 cups powdered sugar
  • 1 teaspoon vanilla

For the half-recipe of lemon-flavored filling:

  • 2 teaspoons lemon zest chopped fine
  • 2 teaspoons lemon juice

For the half-recipe of maple nutmeg-flavored filling:

  • 1-1/2 tablespoon maple syrup
  • a pinch (okay, 1/16 teaspoon or maybe less) freshly grated nutmeg

Instructions

  • Make the cookies. Preheat oven to 350ºF. Prepare baking sheets with parchment paper—you won’t need oil or butter.
  • In a large bowl, using an electric hand mixer, mix together the canned pumpkin, oil, brown sugar, eggs, cinnamon, ginger , vanilla, allspice and salt. Mix until there are no lumps.
  • Add the baking soda and baking powder. Stir and then add the flour in batches. The dough should be smooth and a little glossy.
  • Drop spoons of batter onto the cookie sheet, leaving about 1-1/2 inches between blobs. Each of mine was about 1-1/2 tablespoon of dough. The dough is very sticky and a little fussy to work, and at times seems to be feeling its way along your hands, and you will have an adventure getting it from the spoon to the sheet. Keep a wet cloth at hand to minimize the damage. (Note to self: move laptop away from work area.)
  • Slide the sheets into the hot oven and bake for 10 to 12 minutes depending on your oven. I did two sheets at a time, three batches. When done, the cookies should be firm to the touch and your tester should come out clean. Lift the cookies off the sheets right away with a spatula and cool completely on racks.
  • Make the filling. While cookies are cooling, put the butter in a big bowl and beat with an electric hand mixer until fluffy, about three minutes. Scrape down the bowl and add the cream cheese. Beat again for about two minutes. Add the vanilla. Add the powdered sugar, one cup at a time. Scrape down the bowl now and then. Pretty quickly, it will take on that lavish look of cream cheese icing, and even if you have done this a hundred times before you will think: say, that was easy! This recipe yields about 2-1/2 cups of cream cheese filling.
  • Make the two flavors of filling. Divide the filling in half into two smallish bowls. In one bowl, add the maple syrup (the filling will have a subtle maple flavor) and grate in the nutmeg—go easy on it. In the other bowl, stir in the 2 teaspoons of lemon zest and the lemon juice.
  • Assemble the whoopie pies. Prepare a plate or surface to hold them—I ended up using pizza pans. If you are making two different fillings, then divide the cookies into two and use two different sheets to sort them. There’s not a lot of visual difference between the fillings, and it’s easy to lose track of which is which (see Kitchen Notes).
  • Hold one cookie flat in your hand, flat bottom side up, dollop on a generous tablespoon of filling, then gently place another cookie on top. Don’t squeeze it. Settle it in place firmly.
  • Slide the whoopie pie-laden sheets into the fridge for a little while to firm them up. That’s it. Done. Store finished whoopie pies in a single layer in airtight containers in the fridge.

Kitchen Notes

Brown sugar. Before you add the brown sugar to the batter, eyeball it for lumps. If it is looking like there are hard stubborn lumps, try to crush them and break them up.
What would I do differently? I would add a tiny drop of yellow food coloring to the lemon filling, because honestly, it was really hard to tell the difference between these two flavors visually. I might also try making the cookies smaller (with a corresponding shorter baking time).
What if you only want one icing flavor? Use the whole filling recipe and double the flavorings.
Whoopie? How did they get that name? Supposedly, because that’s what kids would say when offered one.
Use real maple syrup, not "maple-flavored” stuff. We still have some of the superb maple syrup we got at beautiful Moondance Gardens in upstate New York during sugaring time—but use any kind that you have available.
And finally, fun with cats. After I prepared the lemon zest, I went in the living room and patted the more scornful of our cats. Now you smell like lemon, I said to her.

10 thoughts on “Pumpkin Whoopie Pies Two Ways”

  1. Now *this* is fun! There are still places in Maine where you can buy homemade whoopie pies, which are delicious, but there are so many awful packaged imitations out there. And I don’t think I’ve ever seen pumpkin whoopie pies, so this is going on my list to try post haste.

  2. It’s always important to have fun with cats! I’m pretty sure the internet was invented just so we could all share our cat experiences. Anyway, fun recipe! We’ve never made Whoopie Pies, although I’m sure we will someday. I kind of like to think of them as America’s answer to the macaron. 😉 Love the idea of bourbon. Dark rum would be excellent too. Good stuff — thanks.

  3. I’m one of those weirdos that doesn’t like pumpkin. Makes no sense since I love squash. I used to say that about eggnog until I put an old dark rum in it a week ago. Maybe I’ll be nice and make them for my family but I’d probably eat all of the lemon icing. Not sure If I’ve ever had a whoopie pie of any flavour.

  5. Lydia, please let us know how you like it! After stumbling on them in Syracuse last month we knew we had to try them.

    Kitchenriffs, I agree about the invention of the Internet – the same goes for youtube which until recently was 50% cats batting at paper or falling off beds. Oooh, the dark rum is a good idea! I will be making these again soon due to popular demand (villagers with pitchforks outside my office door – I hear and obey) and will give that a whirl.

    Randi, the lemon icing is definitely wonderful. And if you like spice cake or gingerbread, you will like this, I think.

    Karin, then maybe they still mostly manifest in the eastern half of the country. Also, moon pies = horrific, ew ew ew

  6. Am a huge fan of yours and have tried quite a few of your recipes with accolades for the results. many thanks.

    I´m one of (the maybe two or three) people who had heard of whoopie pies, but hadn´t a clue as to what on earth they were – am most grateful for the enlightenment, and shall try them soon.

    May I ask for a huge favor? since you obviously are very much attuned to recipes in general, could you please steer me to any sites which specialize in diabetic (sugarless) sweets. We diabetics are worse than ants, maybe because they are such no-nos. A big hug from Brazilian foodies, especially me.

  7. Terry – I let out a big whoop when I saw this today – how did you know I’ve been longing for a pumpkin whoopie pie recipe? Thank you , thank you, thank you!

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