Home > Desserts > Pumpkin Whoopie Pies Pumpkin Whoopie Pies September 20, 2020 | 8 Comments SAVE TO RECIPE BOX Jump to Recipe This post may contain affiliate links. Please read my disclosure policy. Smooth and velvety cream cheese frosting sandwiched between two soft, chewy, thick, and rich pumpkin cookies — Pumpkin Whoopie Pies are the ultimate fall treat! Pumpkin Whoopie Pies I can’t believe I haven’t shared more whoopie pie recipes in the past seven years of creating recipes, but after this pumpkin version, to say I’m hooked would be an understatement. Be prepared for a million different whoopie pie variations in the coming months! Pumpkin Whoopie Pies are soft, cake-like, and packed with great pumpkin flavor. What is a whoopie pie? In case you aren’t familiar, a whoopie pie is either a cookie, pie, sandwich, or cake — usually 2 round mound-shaped pieces of a flavored cake with a sweet and creamy filling sandwiched in between. These Pumpkin Whoopie Pies start with two thick, chewy pumpkin cookies with a thick layer of sweet and tangy cream cheese frosting inside! I’ve always been a believer that it’s the little things that make baked goods to turn out their best. With that in mind, let me share a few tips that will get these Pumpkin Whoopie Pies tasting their best. Pumpkin Whoopie Pie tips Watch the baking time. I like to *slightly* underbake these cookies to keep them soft, moist and a little bit dense. If they are overbaked they lose their awesome texture and a lot of the flavor. The pumpkin matters. For this recipe, you’ll want to use pure canned pumpkin and not pumpkin pie filling. Pumpkin pie filling has a lot of added ingredients, as opposed to pure pumpkin which is just pumpkin. We love Libby’s® pumpkin because it is thick, not watery, and very consistent from can to can (not sponsored). If you have wet pumpkin, you may need to dab it off a bit with some paper towels first. Accurately measure the flour. If you press a measuring cup into a bag of flour you will pack in way too much flour. To accurately measure your flour, spoon the flour into the measuring cup until its overfilled. Then use the back of a table knife to level the measuring cup at the top. You’ll have a perfect flour measurement now! Bake on a Silpat® liner or parchment paper. To help the cookie part of these Pumpkin Whoopie Pies bake evenly (and keep the bottoms from over-browning), I recommend a good baking mat. Parchment paper also works. I don’t recommend lining the pan with foil. Next, let’s chat frosting! Cream Cheese Frosting Set out the butter and cream cheese about an hour in advance to get them to room temperature. If these ingredients are cold, they won’t combine as smoothly with the possibility of unpleasant cream cheese chunks in the frosting. Here are some tips for how to bring cream cheese and butter to room temperature quickly. Slowly add in the powdered sugar. Add more or less powdered sugar according to personal preferences. For these whoopie pies, we want the frosting a bit firmer so it doesn’t squish out when taking a bite. More sugar will make the frosting sweeter and firmer, less sugar will leave the frosting a bit tangier and softer. Let cookies cool fully. Before frosting the inside of these Pumpkin Whoopie Pies, make sure they are completely cool. Otherwise, the frosting will begin to melt and change consistency. Storing Pumpkin Whoopie Pies Storing BAKED Cookies Unlike most cookie recipes, these pumpkin whoopie pies do not store well beyond a day at room temperature. Because of the canned pumpkin and how moist these cookies are, they get sticky when kept at room temperature for more than a day. To combat this, I’ve found that freezing any leftover unfrosted cookies after the first day works well. Freezing UNBAKED Cookies Drop the unbaked cookie dough balls on a large sheet pan and freeze until solid. Once solid, transfer the frozen dough balls to an airtight container/bag separated by parchment paper (so they don’t all stick together in one clump) and freeze for up to 3 months. To bake: You can bake them straight from the freezer; just add 1-3 minutes onto the cooking time (or thaw the dough in the fridge and bake according to directions). QUICK TIPFreezing cream cheese frosting: I haven’t had success with freezing and thawing cream cheese frosting or frosted Pumpkin Whoopie Pies. Because of the dairy in cream cheese frosting, it tends to separate and become an unpleasant texture. It also makes the cookies wet and soggy. QUICK TIPPumpkin pie spice is a delicious combination of warming spices (like cinnamon, nutmeg, ginger, cloves and allspice). It can be found among other spices in the grocery store, or you can make your own! Pumpkin pie spice adds loads of flavor to these Pumpkin Whoopie Pies; feel free to increase the amount for a more strongly spiced cookie. Use leftover pumpkin in one of these recipes Pumpkin Snickerdoodles thick and chewy! Pumpkin Overnight Oats nutritious breakfast option Kid-friendly hot beverage: Pumpkin Spice Latte Steamer Pumpkin Cupcakes with cinnamon-cream cheese frosting Gluten-Free Pumpkin Cake with chocolate chips FOLLOW ALONG! Subscribe to my newsletter and follow along on Facebook, Pinterest and Instagram for the latest updates, recipes and content. Pumpkin Whoopie Pies 5 from 3 votes - Review this recipe Smooth and velvety cream cheese frosting sandwiched between two soft, chewy, thick, and rich pumpkin cookies -- Pumpkin Whoopie Pies are the ultimate fall treat! SAVE TO RECIPE BOX Print Recipe Pumpkin Whoopie Pies 5 from 3 votes - Review this recipe SAVE TO RECIPE BOX Print Recipe Smooth and velvety cream cheese frosting sandwiched between two soft, chewy, thick, and rich pumpkin cookies -- Pumpkin Whoopie Pies are the ultimate fall treat! Course Dessert, Snack Cuisine American Keyword pumpkin whoopie pies Prep Time 30 minutes Cook Time 10 minutes Optional Chilling Time 30 minutes Total Time 1 hour 10 minutes Servings 25 -27 whoopie pies Calories 278kcal IngredientsParchment paper or Silpat linerCookies2 and 1/2 cups (328g) white, all-purpose flour (See Note 1)1 teaspoon baking soda1 teaspoon baking powder2 teaspoons ground cinnamon1 and 1/2 teaspoons pumpkin pie spice1/2 teaspoon fine sea salt3/4 cup (152g) granulated white sugar3/4 cup (144g) light brown sugar, lightly packed1/2 cup (8 tablespoons; 113g) unsalted butter, softened, not melted1 CUP (222g) canned pumpkin (not an entire can of pumpkin; don't use pumpkin pie filling)1 large egg1 teaspoon vanilla extractCream Cheese Frosting4 ounces (115g) full-fat cream cheese (the block cream cheese, not spreadable), softened, not melted4 tablespoons (56g) unsalted butter softened, not melted2 cups (242g) powdered sugar1/8 teaspoon fine sea salt1 teaspoon vanilla extract InstructionsPREP: Prepare a large sheet pan by lining with parchment paper or a Silpat liner (very important to avoid burned bottoms on these cookies). Preheat oven to 350 degrees F.DRY INGREDIENTS: Add flour, baking soda, baking powder, cinnamon, pumpkin pie spice, and salt to a large bowl; whisk to combine and set aside.WET INGREDIENTS: In a medium bowl, cream together the butter, white sugar, and brown sugar until smooth and creamy. Add 1 cup pumpkin, the egg, and vanilla. Beat until the mixture is creamy. Add in the dry ingredients and mix until JUST combined. Avoid overmixing, as it will create dense cookies.OPTIONAL -- CHILL DOUGH: Cover tightly and chill the dough for 30 minutes up to 10 hours. Chilling is not necessary but it makes the dough much easier to work with and intensifies flavors.ROLL COOKIE BALLS: Use a 1 tablespoon measuring spoon to scoop out balls of dough. Each cookie should be about 1 tablespoon in size. Once dough is in the tablespoon measuring spoon, use a small spoon to scoop it onto the lined sheet pan. Try to smooth or round the balls, but it's okay if they're a bit bumpy; this dough is difficult to work with. Leave 2 inches between each cookie (I only bake 8-10 cookies at a time) and flatten the balls of dough slightly. (This batter is wetter than normal cookie dough so don't be alarmed that you can't roll out balls of dough; chill in the fridge for additional time if needed to make it easier to get cookie dough balls on a tray).BAKE: Bake for 8-13 minutes (9-10 minutes is perfect for my oven) watching carefully to avoid over-baking. We like these slightly under-baked and soft, but the tops shouldn't be shiny or wet looking at all. Remove and allow cookies to stand for 3-5 minutes on the sheet pan before removing to a wire cooling rack to finish cooling.FROSTING: Meanwhile, make the frosting. In a stand mixer fitted with the whisk attachment (or a large bowl and a hand mixer), beat the softened (not melted) cream cheese and butter until creamy for about 2 minutes at medium-high speed. Add the powdered sugar, salt, and vanilla. Beat until everything is combined and the frosting is soft and creamy. Avoid over-beating the mixture or you'll get whipped frosting.FROST COOKIES: Generously frost half of the cooled cookies. Sandwich the other half of the cookies on top. STORAGE: Do not store the cookies in plastic containers. Store on plates loosely covered with foil in the fridge. Best eaten same day or within 1-2 days. After that, they soften too much and the texture degrades. Freeze unbaked cookie dough balls for up to 3 months; bake straight from freezer for an additional 1-3 minutes. Video Recipe NotesNote 1: If you press a measuring cup into a bag of flour, you will pack in way too much flour; use a spoon to scoop it into a measuring cup and then level the top with the back of a table knife. Nutrition FactsCalories: 278kcal | Carbohydrates: 52g | Protein: 4g | Fat: 6g | Saturated Fat: 4g | Cholesterol: 23mg | Sodium: 158mg | Potassium: 70mg | Fiber: 1g | Sugar: 33g | Vitamin A: 1663IU | Vitamin C: 1mg | Calcium: 42mg | Iron: 1mg DID YOU MAKE THIS RECIPE? I love hearing from you when you've made one of my recipes! Tag me on Instagram at @ChelseasMessyApron or leave me a comment below.