In a mixer with a paddle attachment, combine butter and sugars. Mix until light and fluffy.
Add pumpkin, egg, and vanilla. Mix until combined.
In a large bowl, whisk together dry ingredients. Add them to wet ingredients and mix on a slow speed until just combined.
Stir in 1 cups or caramel chips, 1 cup of caramel bits and 1 cup of chocolate chips.
Place the dough in the fridge for at least 2 hours.
Preheat the oven to 350 degrees and prepare a baking sheet with parchment paper.
Use a large cookie scoop to scoop out balls of dough - about 6 to a sheet.
Bake for 14-16 minutes.
Allow cookies to cool on baking sheet.
While the cookies are cooling, combine 1 cup of caramel bits and 1 teaspoon of water. Microwave in 30 second intervals, stirring between each, until caramel is melted.
Place caramel in piping bag and drizzle it over the cookies.