I didn’t set out to create whoopie pies today—just hunting for coffee when that can of pumpkin purposively called my name. Before I knew it, my counter was dusted in flour and sugar, and I was grinning at the idea of pumpkin-spiced cake rounds hugging creamy filling. These pies feel like tiny fall sandwiches—and honestly, their slightly lopsided imperfections make them even more lovable. My first try resulted in a trio of uneven circles—one flat, one domed like a hill, and one with a cute little crack that I dubbed my “signature pie.” Taste? Still top-tier. The batter whipped together thick and dreamy, dotted with warm spices and pumpkin. There was one moment where I thought, “This is too orange,” but once baked, the balance of pumpkin and sugar made everything feel just right. Piping the filling came next and, naturally, I squeezed a bit too much out, and yes—filling spilled, fuzzy—the saucy edges caught on my fingertips, and I licked off every bit before it had a chance to make a mess elsewhere. It’s the little joys. When they cooled, I pressed two cake rounds together with that soft cream center, and my cat gave me a look that said, “Where’s mine?” The filling squeezed out the sides in the most heartwarming way, like a hug that’s a bit too long, but oh-so-satisfying. I stacked them in a pile that teetered and questioned if these should maybe a “whoopie tower” instead. Totally wobbly and absolutely perfect. These whoopie pies are forgiving. Slightly cracked tops? Hidden by filling. Irregular shapes? Whimsical. Too much filling? Luxuriously messy. You bite into one and warm pumpkin cake gives way to soft, sweet frosting, and you close your eyes for a second thinking, yes—the world can wait while I savor this. A few vanished before I managed to offer them to anyone else. If a recipe know how to feel like a memory, it’s these: tender cake, fluffy center, sweetness tucked in every edge. And yes, I’ll absolutely make them again tomorrow—maybe with a cheeky drizzle of chocolate or a tiny sprinkle of flaky sea salt. But right now, I’ll just sit here with my signature pie, flaky crumbs between my fingers, feeling fall in a bite.
Detailed Ingredients with measures
- 1½ cups all-purpose flour
- ½ teaspoon salt
- 1½ teaspoons baking soda
- ½ teaspoon ground cinnamon
- ½ teaspoon ground ginger
- ¼ teaspoon ground nutmeg
- ¼ teaspoon ground cloves
- ½ cup unsalted butter, softened
- ¾ cup light brown sugar, packed
- 1 large egg
- ½ cup pumpkin purée
- 1 teaspoon vanilla extract
- For the filling: ½ cup unsalted butter, softened, 4 oz cream cheese, softened, 2 teaspoons vanilla extract, 2½ cups powdered sugar
Prep Time
About 30 minutes—enough to mix the batter, spread the cream, and sneak a taste.
Cook Time, Total Time, Yield
Cook Time: 10–12 minutes until cake tops spring back softly. Total Time: Around 1 hour, counting baking, cooling, and stacking. Yield: Makes about 16 whoopie pies—though quality testing may reduce that number a bit.
Detailed Directions and Instructions
Preheat, line, and gather pumpkin essentials
Start by preheating your oven to 350°F and lining your baking sheets with parchment so cookies will slide off. Gather flour, cozy spices, pumpkin puree, sugar, oil, eggs, and vanilla. Even at this early stage, the autumn vibes are touching down.
Whisk dry spices and flour lovingly
In a large bowl, whisk together flour, baking soda, baking powder, a scant pinch of salt, ginger, cinnamon, and cloves. Your air might fill with spice perfume, which could inspire you to taste-test—totally acceptable.
Mix wet pumpkin goodness
In another bowl, whisk pumpkin puree with sugar, oil, eggs, and vanilla until smooth and blissfully thick. The batter glows orange and makes you want to scoop it by the spoonful, even though restraint is wise (not always practiced in my kitchen, though).
Fold wet into dry with love
Pour the pumpkin mixture into your spiced flour bowl. Gently stir just until everything looks evenly moistened—no white streaks should remain, but don’t overmix. The texture should feel soft and just a touch dense, not gloopy.
Scoop, bake, and resist opening early
Use a small ice-cream scoop—about two tablespoons—to drop round, paired cookies onto your prepared sheets. Bake one tray at a time for 12 to 15 minutes, until the tops appear dry and a toothpick comes out clean. It’s okay to peek at around 11 minutes, but don’t let impatience win. Let them cool right on the pan briefly, then slide them to a rack—two minutes on hot pans and they’ll turn funky.
Whip the dreamy cream-cheese filling
While the cookies cool, beat soft butter and cream cheese until smooth, then add vanilla and powdered sugar a bit at a time until thick and dreamy. Stir until it looks like frosting clouds. You might swipe a bit with a finger—worth every sugar whisper.
Assemble and chill for claims
Spread or pipe the filling on flat sides of half the cookies, then press another cookie gently on top. Give them a chill in the fridge for about half an hour so the filling sets. Then store or attack immediately—either mood is valid.
Notes
Don’t skip chilling or timing
Too-warm cookies make a mess when you sandwich them. Cool before assembly or risk drippy disasters.
Spices can be playful
If you’re bold, nudge up the ginger. Want subtle warmth? tone down the sprinkle. Either way—taste as you go.
Even scoops equal matching tops
Scooping evenly means each pie halves pair up like puzzle matches—not frustrating mismatches.
Storage makes them better
These keep in the fridge up to a week (if they even survive that long) and freeze well too. Thaw slowly for soft, spice-warmed kisses.
Cook techniques
Use real pumpkin puree, not pie filling
Grab a can that says 100% pumpkin puree, promise me. Pie filling already has sugar and spices—been there, made a way-too-sweet batch—and different brands can be watery. I reach for a thick puree so the batter stays cuddly, not sloshy. If yours looks thin, don’t be shy about switching brands next time.
Measure flour gently (your cookies will thank you)
A heavy hand turns these into stodgy little pucks. Fluff the flour, spoon it in, level it off—or use a scale if you’ve got one. The day I scooped straight from the bag, I swore my mixer sighed at me. Light touch = pillowy, cake-y cookies.
Cozy batter beats tough batter
Bring the eggs to room temp so they mingle smoothly, then stir until the streaks disappear and stop. Overmixing is where tenderness goes to die. I’ve done the enthusiastic-stir routine and, yeah, the texture paid the price. Quick dip eggs in warm water if you forgot.
Scoop neat, bake calm
A small ice cream scoop—about 2 tablespoons—keeps cookies the same size so every one finds a perfect partner. Space them about an inch apart and bake one sheet at a time for 12 to 15 minutes, just until the centers look dry and a toothpick comes out clean. Parchment keeps things easy-breezy.
Cool, fill, then chill (ask me how I know)
Let cookies rest 5 minutes on the pan, move to a rack, and cool completely. Beat room-temp unsalted butter with full-fat block cream cheese for that plush, tangy filling. If you rush assembly, the filling will try to slide away like a sugar avalanche—so sandwich, then chill 30 minutes.
Make-ahead without the mush
Party tomorrow? Stash cookies and filling separately in the fridge, then assemble later so nothing gets squished in storage. A piping bag makes you feel fancy, but a spoon totally works when life (or dishes) are chaotic.
Storage that keeps them soft, not sticky
Pumpkin makes these extra moist, which is lovely—until they sit out. Keep them covered in the fridge for up to a week, or wrap tight and freeze for those late-night snack emergencies (hello, three months).
FAQ
Can I use pumpkin pie filling instead of puree?
I wouldn’t. Pie filling is pre-sweetened and spiced, so the cookies go overboard. Stick with 100% puree; thicker brands behave better in batter.
Why are my whoopie pies sticky?
It’s the pumpkin doing its moist magic. Once cooled, keep them refrigerated and covered; that’s how you dodge the tacky tops.
How big should each cookie be and how long do I bake?
Scoop about 2 tablespoons per cookie and bake one pan at a time for 12 to 15 minutes, until the centers look dry and a toothpick tests clean.
How do I avoid runny or lumpy filling?
Start with room-temperature unsalted butter and full-fat block cream cheese, then beat until smooth. Don’t sandwich warm cookies, and chill assembled pies before serving.
Can I make these ahead or freeze them?
Yes. Store cookies and filling separately in the fridge, assemble later, and refrigerate finished pies up to a week. For longer, freeze well-wrapped for about three months.
Forgot to warm the eggs—help?
Pop them (still in their shells) into warm tap water for about 5 minutes, then carry on like the kitchen hero you are.
Conclusion
You’ve just baked Preppy Kitchen’s pumpkin whoopie pies, and oh boy—what a cozy pumpkin hug between cakey rounds this is. The batter itself is dreamy: pumpkin puree, brown sugar, a touch of molasses, eggs, oil, milk, and that warm blend of spice that feels like fall in a bowl. I’ll admit, my mixer spat some batter onto the backsplash once—I admired the splatter for a moment before laughing and wiping it up. That’s the kind of kitchen trophy we take pride in. Pipe or drop rounds of batter onto the baking sheet, and watch them puff up. They puff, they crack just a little, and those tops look like miniature autumn moons winking at you. I nudged one too early and the edge crumbled—but that just became mid-bake taste testing, so zero regrets. When they come out, each cookie is golden-edged, tender, and still warm enough to be dangerously quick to pair. Then comes the filling—softened butter whipped with cream cheese, vanilla, a dash of spice, and a whisper of powdered sugar until it’s fluffy solar-cloud level. I may have overfilled a piping bag once, and frosting squished out from the top—flavor everywhere, zero complaints. Sandwich it between two warm pumpkin discs, and the first bite is a chewy pumpkin cake giving way to pillowy tangy frosting. It’s that moment you close your eyes and taste cinnamon leaves and pumpkin cider all at once. You might find crumbs in your hair or a little frosting smudge on your shirt—but that’s your fall baking badge. And honestly, leftovers? Even better. The cookies stay so soft they practically melt in your mouth long after bake day. I’ve walked by the counter and snagged one only to realize it was gone in two bites. Worth it every time.
More recipes suggestions and combination
Pumpkin Whoopie Pie Ice Cream Sandwiches
Grab your cooled pumpkin cakes and a scoop of vanilla or caramel ice cream, press them together, freeze a beat—then bite into cold pumpkin cake and melting ice cream. Mine oozed at the edges immediately, but the mess was part of the thrill.
Pumpkin Whoopie Pie Trifle
Crumbled whoopie pies layered with whipped cream, pumpkin mousse, or even warm cider syrup makes fall in a parfait glass. One of mine dripped down the side, but I just called it “character” and dove right in.
Mini Pumpkin Whoopie Pie Bites on Skewers
Make smaller rounds, sandwich them, then stack on a skewer like festive pumpkin kabobs. I accidentally skewered one sideways and it wobbled like a pumpkin on a stick—but it was adorable and totally snack-worthy. Serve the classic sandwiches when you want that rich, cozy bite. Ice cream versions are for summer-fall mashups. Trifles for special fall gathering oomph. Skewers when you’re feeling whimsical and sweet. Expect crumb tracks, frosting fingerprints, maybe a goofy smile in the mirror—but isn’t that the whole point of baking with heart?
