Prep: Heat oven to 400°F. Then, line a baking sheet with parchment paper, or grease it with non-stick cooking spray, and set it aside.
Dough: In a large bowl beat together the butter and shortening with an electric mixer on medium speed until smooth. Mix in the vanilla extract and the egg and combine well.
Stir in the flour, baking soda, and salt until the dough comes together.
Shape: Roll the cookie dough out onto a lightly floured surface so that it is ⅓ of an inch thick. Cut the dough with an apple-shaped cookie cutter. If you do not have an apple shaped cookie cutter, use a pumpkin-shaped one and turn it upside down as I did.
Bake: Place the cookie cutouts two inches apart on your prepared baking sheet.
Carefully insert 1 inch of the wooden stick into the side of each cookie (where the stem will be). Use a light-handed touch to not disturb the cookie too much. You should be able to feel exactly where the stick is as you are doing this.
Bake in the oven for 6-8 minutes or until the edges are a light brown in color.
Let the cookies cool for 2 minutes on the pan before removing to a wire rack to cool completely.
Topping: If you are using the caramel ice cream topping, add in the flour and mix well until smooth.
If you are using caramel squares, heat them (unwrapped) with the water in a 2-quart saucepan over low heat, stirring frequently until smooth and melted.
Assemble: Spread caramel on the top third of the cookies and hold the cookies up right to allow the glaze to drizzle down the cookie. If it is not spreading, try adding some more caramel until it begins to drizzle down.
If you want to add some extra flare to these cookies, sprinkle with multi-colored candy sprinkles. Other great options for added decoration would be mini M&M's, chopped nuts, mini chocolate chips, really the possibilities are endless!
Be sure to let the cookies set for about an hour for the caramel to harden a bit. Store flat in an airtight container.