Pumpkin Pie Cookies with Custard Filling and Whipped Cream
Pumpkin pie cookies put a spiced pumpkin custard on a wide brown sugar cookie, then finish it the way you’d finish a slice of pie: with a swirl of whipped cream and a pinch of spice on top.
The effect? You get every part of the pie without any pie dough to roll out or crimp.
Sounds good? Grab your baking sheet and let’s make it!
Why You’ll Love This Recipe
- The cookie dough needs one bowl, a whisk and a spatula, with no mixer and no butter to soften.
- The filling can be mixed a day ahead
- A batch makes 15 to 18 generous cookies, enough to cover a dessert table.
When and Who This Is For
These belong on the Thanksgiving dessert table, next to the pie or in place of it, and at any fall dinner where dessert goes around on a tray.
They’re a serve-at-home cookie. The custard filling needs the fridge and the whipped cream goes on at the last minute, so for a bake sale, a lunchbox or a tin that has to travel, my soft pumpkin cookies with chocolate chips are the better pick.
They’re vegetarian, provided your whipped cream has no gelatin in it, so check the label if you’re buying it ready-made. If you need a pumpkin cookie without dairy or eggs, my vegan pumpkin chocolate chip cookies are the one to make instead.
Ingredients
For the cookies
- ½ cup (113 g) unsalted butter, melted
- 1 cup (213 g) brown sugar, packed
- ½ cup (100 g) granulated sugar
- 2 large eggs
- 1½ teaspoons (7.5 ml) vanilla extract
- 3 cups (360 g) all-purpose flour
- 1½ teaspoons (9 g) baking soda
- ½ teaspoon (2 g) baking powder
- ¼ teaspoon (1.5 g) salt
- 2 teaspoons (5 g) pumpkin pie spice
For the pumpkin pie filling
- ⅔ cup (163 g) pumpkin puree
- 1 large egg
- ¼ cup (53 g) brown sugar, packed
- 2 tablespoons (30 ml) milk
- 1 teaspoon (5 ml) vanilla extract
- 2 teaspoons (5 g) cornstarch
- ½ teaspoon (1 g) pumpkin pie spice
For the topping
- Whipped cream, homemade or ready-made
- Pumpkin pie spice, for dusting
Brown sugar. Light or dark both work. Dark brown sugar carries more molasses and gives a deeper color, while light brown bakes up paler.
Pumpkin puree. Use plain canned pumpkin, the kind labeled 100% pumpkin, and not canned pumpkin pie filling (more on that in the questions below). ⅔ cup is a little over a third of a 15 ounce can, which leaves roughly a cup for a batch of pumpkin coffee cake cookies, pumpkin spice latte with almond milk or high protein pumpkin overnight oats, which take the same ⅔ cup.
Pumpkin pie spice. It’s also sold as pumpkin spice, and it’s usually a blend of cinnamon, ginger, nutmeg and cloves with no pumpkin in it at all. It goes into the dough, the filling and the topping. The dough on its own is really a pumpkin pie spice cookie recipe, since every bit of the pumpkin lives in the filling.
How to Make Pumpkin Pie Filled Cookies
- Heat the oven to 350°F (175°C) and line a rimmed baking sheet with parchment.
- Melt the butter and let it sit for a few minutes, so it’s warm rather than hot. Pour it into a large bowl and whisk in both sugars until combined.
- Whisk in the eggs and vanilla until the mixture is smooth and glossy.
- Spoon the flour into your measuring cup and level it off rather than scooping it straight from the bag, since packed flour makes a drier dough that’s more likely to crack when you press the wells. Stir the baking soda, baking powder, salt and pumpkin pie spice through the flour with a fork, so no cookie ends up with a pocket of baking soda. Add it all to the bowl and fold with a rubber spatula until no dry flour is left. Expect a thick, soft, glossy dough, closer to a heavy paste than a firm cookie dough.
5. Scoop the dough with a 2 inch (5 cm) cookie scoop onto the baking sheet, spacing the balls about 2 inches (5 cm) apart. Eight fit on a standard half sheet.
6. Press a deep well into the center of each ball with your thumb or the back of a rounded measuring spoon, keeping a wall of dough all the way around and taking care not to press through the bottom. The rims will look a little ragged, and that’s fine. Pinch together any crack that runs right through the wall, because that’s where filling escapes.
7. Put the tray in the freezer for 10 minutes. This firms the dough so the walls hold when the filling goes in.
8. While the dough is in the freezer, make the filling. Whisk the pumpkin puree, egg, brown sugar, milk and vanilla in a smaller bowl until smooth, then add the cornstarch and pumpkin pie spice and whisk again. It comes out smooth, pourable and brown rather than bright orange, thanks to the brown sugar and spice.
9. Take the tray out of the freezer and spoon about 2 teaspoons of filling into each well, stopping just below the rim. An overfilled well tends to run over in the oven and glue the cookie to the parchment.
10. Bake for 12 minutes, until the cookies have spread and the edges are golden brown. They spread wide as they bake, and the filling spreads with them, settling into the top so it comes out darker and marbled instead of sitting in a neat circle. That’s how it should look. The filling should look set rather than wet or wobbly when you take them out.
11. Leave the cookies on the sheet for 5 minutes, since they’re soft straight out of the oven, then move them to a wire rack to cool completely.
12. Repeat with the rest of the dough, keeping it in the fridge between trays. Give every tray its own 10 minutes in the freezer before filling. If you’re working with one baking sheet, let it cool before the next batch goes on, because a hot pan starts softening the dough right away.
13. Right before serving, pipe or spoon whipped cream onto each cookie and dust it with pumpkin pie spice. Wait until the cookies are completely cool first, because any warmth left in them will melt the cream.
Tips and Variations
Brown the butter. Cook the butter in a light-colored saucepan over medium heat, stirring, until it foams, smells nutty and brown flecks form on the bottom, about 5 to 8 minutes. Scrape it into your mixing bowl, brown bits and all, and let it cool for 10 to 15 minutes before the sugars go in. The dough comes out a shade darker.
Pipe the tops ahead with stabilized cream. Plain whipped cream starts to weep after a few hours. If you’d like the cookies topped before guests arrive, a stabilized whipped cream made with a little gelatin or cream cheese holds its shape much longer in the fridge. The gelatin version isn’t vegetarian, so skip it if that matters at your table.
Ways to Serve Them
- Cold or at cool room temperature. If you’ve had Crumbl’s seasonal Pumpkin Pie cookie, that one is served chilled too.
- As a top-your-own tray: set out the cooled, bare cookies with a bowl of whipped cream and a small dish of pumpkin pie spice, and let everyone finish their own.
- With coffee after dinner, especially with a splash of homemade pumpkin spice coffee creamer stirred in.
- Next to a pitcher of Thanksgiving vodka drink for the grown-ups, which brings apple, vanilla and cinnamon to the dessert table.
Questions You May Have About These Cookies
Do pumpkin pie cookies need to be refrigerated?
Yes. The filling is an egg and milk custard, the same kind of filling as pumpkin pie. The USDA’s advice for egg-rich pies is to refrigerate them once they’ve cooled and not to leave them out for more than two hours. Keep the cookies in an airtight container in the fridge, in a single layer or with parchment between the layers so they don’t stick together, and eat them within 3 days. They soften a little as they sit. Leave the whipped cream off until you serve them, since it doesn’t hold up in storage.
The recipe calls it pumpkin pie filling. Does that mean the canned kind?
No. Here, pumpkin pie filling means the custard you whisk together yourself from plain pumpkin puree, an egg, brown sugar, milk and spice. The canned product sold as pumpkin pie filling, sometimes labeled pumpkin pie mix, already contains sugar and spice, so using it here would double both. Look for a can that says 100% pure pumpkin.
Why did the filling spill over the edge?
Most leaks in pumpkin pie filled cookies come down to one of four things:
– The well was filled right to the top.
– The dough warmed up before baking, from a skipped freeze or a later tray shaped from dough that sat out.
– A crack ran through the wall.
– The well was pressed so deep that the bottom got too thin.
Fill to just below the rim, give every tray its 10 minutes in the freezer, and pinch cracks closed as you shape them.
Can I make them ahead of time?
Yes, in parts. The filling can be whisked a day ahead and kept covered in the fridge. The baked cookies, without the whipped cream, keep in the fridge for up to 3 days, so baking them the day before a dinner works well. For longer, freeze the cooled, bare cookies in a single layer until firm, then pack them into an airtight container for up to 2 months. Thaw them in the fridge overnight, and the filling may be a little softer. Add the whipped cream and spice just before serving.
Related Recipes
- Pumpkin Coffee Cake Cookies with Vanilla Glaze. Flat, chewy pumpkin cookies under a brown sugar streusel, finished with a drizzle of vanilla glaze.
- Soft Pumpkin Cookies with Chocolate Chips. Tall, tender and fine at room temperature for days, which makes them the pumpkin cookie for bake sales and lunchboxes.
- Pumpkin Pie Spice Milkshake with Vanilla Ice Cream. Pumpkin puree, vanilla ice cream and pumpkin pie spice blended thick, with whipped cream on top.
Pass the Tray
Pass these proudly around the table after dinner and everyone takes one without waiting for a slice to be cut. Save this to your Thanksgiving board on Pinterest so it’s ready when the planning starts. 🥧
Pumpkin Pie Cookies with Custard Filling and Whipped Cream
Ingredients
Cookies
- 1/2 cup unsalted butter, melted 113 g
- 1 cup brown sugar 213 g, packed
- 1/2 cup granulated sugar 100 g
- 2 large eggs
- 1 1/2 tsp vanilla extract 7.5 ml
- 3 cups all-purpose flour 360 g
- 1 1/2 tsp teaspoons baking soda 9 g
- 1/2 tsp teaspoon baking powder 2 g
- 1/4 tsp teaspoon salt 1.5 g
- 2 tsp pumpkin pie spice 5 g
Pumpkin pie filling
- 2/3 cup pumpkin puree, plain, NOT pumpkin pie filling 163 g
- 1 large egg
- 1/4 cup brown sugar 53 g, packed
- 2 tbsp milk 30 ml
- 1 tsp vanilla extract 5 ml
- 2 tsp cornstarch 5 g
- 1/2 tsp pumpkin pie spice 1 g
Topping
- Whipped cream homemade or ready-made
- pumpkin pie spice for dusting
Instructions
- Heat the oven to 350°F (175°C) and line a rimmed baking sheet with parchment.
- Melt the butter and let it cool for a few minutes. Pour it into a large bowl and whisk in both sugars.
- Whisk in the eggs and vanilla until smooth.
- Stir the baking soda, baking powder, salt and pumpkin pie spice into the flour. Add to the bowl and fold with a spatula until no dry flour remains.
- Scoop with a 2 inch (5 cm) cookie scoop onto the sheet, 2 inches (5 cm) apart, about 8 per sheet.
- Press a deep well into each ball without pressing through the bottom. Pinch closed any cracks in the walls.
- Freeze the tray for 10 minutes.
- Meanwhile, whisk the pumpkin puree, egg, brown sugar, milk and vanilla until smooth, then whisk in the cornstarch and pumpkin pie spice.
- Fill each well to just below the rim, about 2 teaspoons each.
- Bake 12 minutes, until the cookies have spread, the edges are golden brown and the filling looks set.
- Cool on the sheet for 5 minutes, then on a wire rack until completely cool.
- Repeat with the remaining dough, freezing each tray for 10 minutes before filling.
- Just before serving, top each cookie with whipped cream and a dusting of pumpkin pie spice.
Notes
- Storage: refrigerate once cool in an airtight container, in a single layer or with parchment between layers, for up to 3 days. Don’t leave them out for more than 2 hours. Add the whipped cream just before serving.
- Make ahead: the filling keeps covered in the fridge for 1 day. Bare baked cookies freeze for up to 2 months; thaw in the fridge overnight.
- Timing: the total covers the first tray, including 10 minutes in the freezer and cooling.
