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Preheat oven to 375 degrees F. Lightly grease 10-inch cast iron skillet.
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In bowl of stand mixer with paddle attachment, add butter, brown sugar and granulated sugar. On medium-high speed, beat 3–4 minutes until light and fluffy. Stop to scrape sides of bowl with spatula.
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To bowl of stand mix with butter/sugar mixture, add pumpkin puree, egg and vanilla extract and mix on low until combined. Then add flour, baking soda, salt and spices and mix on low until combined.
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Remove bowl from mixer and fold in chocolate chips and chopped pecans.
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Spread batter evenly into prepared skillet.
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In medium mixing bowl, whisk together all pecan pie topping ingredients except pecan halves.
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Across top of cookie, sprinkle pecan halves and pour pecan pie topping evenly.
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Bake 25-30 minutes, until toothpick inserted in center comes out clean and edges are browned. (Note: The longer the cookie bakes, the more cake-like it becomes.)
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Remove to baking rack to cool 15 minutes. Slice and serve warm on plates or in bowls. Serve with whipped cream or ice cream, if desired.