Pumpkin Drop Cookies with Caramel Icing

These Pumpkin Drop Cookies with Caramel Icing are the kind of old-fashioned fall cookie that earns a permanent spot in the recipe box. The pumpkin keeps them soft, moist, and almost cake-like, while cinnamon gives every bite a warm, familiar aroma. They are tender rather than crisp, with lightly golden edges and a fluffy center.

The caramel-style icing is what makes this collected recipe especially memorable. Brown sugar, butter, and milk create a rich cooked base, while confectioners’ sugar turns it into a creamy frosting that settles beautifully over the warm cookies. They are sweet and generously frosted, so one cookie is plenty satisfying with coffee or a cold glass of milk.

This is also a wonderfully practical recipe for fall gatherings, bake sales, and after-school treats. The dough is dropped straight onto the baking sheet, so there is no rolling, cutting, or complicated decorating. I especially like recipes like this when I want the house to smell like fall without spending the whole afternoon in the kitchen.

Love this recipe? Pin it to your Fall Cookies board on Pinterest so you don’t lose it!

Ingredients

Pumpkin Cookies

2 cups shortening

2 cups granulated sugar

2 cups canned pumpkin puree

2 large eggs

4 cups all-purpose flour

2 tsp baking soda

1½ tsp ground cinnamon

1 tsp salt

Caramel Icing

1 cup light brown sugar, packed

½ cup whole milk

6 tbsp unsalted butter

2 cups confectioners’ sugar

1½ tsp vanilla extract

Instructions

1. Preheat the oven. Heat the oven to 175°C / 350°F. Line baking sheets with parchment paper or lightly grease them.
2. Make the pumpkin mixture. In a large bowl, beat the shortening, granulated sugar, and pumpkin puree with an electric mixer until smooth and evenly combined. Beat in the eggs.
3. Combine the dry ingredients. In a separate bowl, whisk together the flour, baking soda, cinnamon, and salt.
4. Finish the dough. Gradually mix the dry ingredients into the pumpkin mixture just until no dry streaks of flour remain. Avoid overmixing.
5. Portion the cookies. Drop generous spoonfuls of dough onto the prepared baking sheets, leaving about 2 inches between cookies.
6. Bake. Bake at 175°C / 350°F for about 10 minutes, or until the edges are lightly golden and the centers are set. Let the cookies rest briefly on the pan, then transfer them to a wire rack.
7. Cook the caramel base. While the cookies bake, combine the brown sugar, milk, and butter in a saucepan. Cook over medium-low heat, stirring regularly, until the butter melts and the sugar dissolves.
8. Finish the icing. Remove the saucepan from the heat and let the mixture cool slightly. Stir in the confectioners’ sugar and vanilla until smooth and spreadable.
9. Frost the cookies. Spread the caramel icing over the cookies while they are still slightly warm. Allow the icing to set before storing or serving.

Cooking Notes

Because these are cake-like drop cookies, do not wait for the tops to become deeply browned. The edges should show just a little color, and the centers should spring back gently when touched.

Use 100% pumpkin puree, not pumpkin pie filling. Pie filling contains added sugar and spices that will change both the sweetness and consistency of the dough.

Measure the flour carefully. Scooping directly from a tightly packed flour container can add too much flour and produce dry cookies. Spoon the flour into the measuring cup, then level the top.

Allow the cooked brown sugar mixture to cool slightly before adding the confectioners’ sugar. If the icing becomes too thick, stir in milk 1 tsp at a time. If it is too loose, add a little more confectioners’ sugar.

The original recipe is unusually generous, particularly in shortening and sugar. For best results, treat the stated yield of 18 as 18 large, rich cookies rather than small everyday cookies.

Nutrition

Estimated Serving Size: 1 large frosted cookie
Yields: 18 servings

Estimated Nutrition per Serving

Calories: 540 kcal
Fat: 28.0 g
Carb: 71.0 g
Protein: 4.0 g

These values are estimates; exact nutrition varies with shortening, milk, butter, pumpkin, ingredient brands, and the amount of icing applied to each cookie.

Recipe Science

These cookies use pumpkin puree as both a flavoring and a significant source of moisture. Unlike crisp cookies, the formula contains a substantial amount of pumpkin and relatively little structural egg compared with the overall batch. Flour provides the framework, while baking soda encourages lift and contributes to the tender, cake-like result. Cinnamon complements pumpkin’s mild earthy sweetness without overwhelming it.

Shortening contributes tenderness because it is essentially fat without the water found in butter. The cookies therefore remain soft while developing only modest browning. During the short baking period, the flour starches gelatinize, egg proteins set, and leavening expands the dough. The icing uses dissolved brown sugar and butter for caramel-like flavor, while confectioners’ sugar provides enough fine sugar to turn the cooked mixture into a spreadable frosting.

These cookies can be prepared ahead and stored in an airtight container after the icing has completely set. Because pumpkin-based cookies retain considerable moisture, separating layers with parchment or wax paper helps prevent sticking. For longer storage, unfrosted cookies generally freeze more conveniently; thaw them before icing.

Dietary Notes & Health Alerts: This is an indulgent dessert rather than a nutritionally light snack. Based on the supplied nutrition information, saturated fat is about 9 g per cookie, or 45% of the FDA Daily Value of 20 g, making it high in saturated fat. The recipe is also very sugar-dense. For a lighter variation, smaller cookie portions are the most straightforward way to reduce calories, saturated fat, and sugar per serving without substantially altering the baking chemistry.

Why You’ll Love This Recipe

• Exceptionally Soft Texture: Pumpkin gives the cookies a moist, fluffy crumb that stays tender rather than turning crisp.
• Caramel-Topped: The cooked brown sugar and butter icing adds a richer flavor than a standard powdered sugar glaze.
• No Rolling Required: Simply mix, scoop, and bake; there are no cookie cutters or chilling steps.
• Made for Fall: Pumpkin and cinnamon deliver classic autumn flavor without requiring an elaborate spice blend.
• Great for Sharing: The large, generously frosted cookies are well suited to bake sales, potlucks, and holiday dessert trays.

FAQ

• Can I use fresh pumpkin instead of canned pumpkin? Yes, but cook and puree it thoroughly, then drain excess liquid. Homemade pumpkin puree can contain considerably more water than canned puree.
• Why are my pumpkin cookies cakey instead of chewy? That’s intentional. The high proportion of pumpkin adds moisture, while the eggs, flour, and baking soda create a soft structure closer to a miniature cake than a crisp cookie.
• Can I make the cookies ahead? Yes. Bake them a day ahead, cool completely, and store them airtight. For the neatest presentation, you can prepare the icing closer to serving.
• Why did my caramel icing get too stiff? Cooked sugar frosting thickens as it cools. Stir in a small amount of milk, about 1 tsp at a time, until it returns to a spreadable consistency.
• Can I freeze these cookies? Yes. Freeze the cooled, unfrosted cookies in an airtight container, then thaw at room temperature and prepare fresh icing before serving.

Conclusion

There is something wonderfully comforting about a soft pumpkin cookie covered in buttery caramel icing, and this collected recipe captures that old-fashioned fall-baking feeling beautifully. Don’t worry about making every cookie perfectly identical; homemade baking is a journey, and a little individuality is part of the charm.

Would you serve these with hot coffee, apple cider, or a cold glass of milk? I’d love to hear your pick. Happy baking from my kitchen to yours!