HEAT oven to 375ºF. Combine brown sugar, peanut butter, shortening, milk and vanilla in the bowl of an electric mixer. Beat at medium speed until well blended. Add egg. Beat just until blended.
COMBINE flour, baking soda and salt in a medium bowl. Add to shortening mixture. Beat at low speed just until blended. Cover and refrigerate about 30 minutes.
DIVIDE dough into thirds. Roll out evenly to 1/4-inch thickness. Using a floured 2 1/2 to 3-inch pumpkin-shaped cookie cutter, cut dough into desired shape and place 2 inches apart on ungreased cookie sheet. Repeat with remaining dough.
To make without pumpkin cookie cutter: PINCH off walnut size pieces of dough. Shape into balls. Place 3-inches apart on ungreased baking sheet. Flatten each ball with bottom of glass to approximately 3/8-inch thickness. Form into pumpkin shape, making indentation on top of round. Pinch off very small piece of dough and roll to form small stem. Attach to top of cookie. With a small sharp knife, score dough with vertical lines to resemble a pumpkin.
BAKE 7 to 8 minutes or until cookies are set and just beginning to brown. Cool on baking sheet 2 minutes. Remove cookies to cooling rack to cool completely.
REMOVE about 1/4 C. vanilla frosting from container and set aside. Add several drops each of red and yellow food coloring to remaining frosting. Blend thoroughly to a bright orange color. Add one drop green food coloring to reserved 1/4 C. vanilla frosting; blend well.
FROST all but the upper “stem” area of cooled cookies with orange frosting. Frost the upper “stem” area with green frosting.
PLACE chocolate chips and shortening in a microwave-safe bowl. Microwave on MEDIUM (50% power) 1 minute. Stir. If necessary, microwave an additional 30 seconds at a time until mixture is smooth when stirred. Transfer chocolate mixture to a resealable food storage bag. Cut small tip off corner of bag. Pipe lines and faces over frosted cookies to resemble jack o’lanterns.
Calories from Fat80g
Total Fat 9g
Saturated Fat 2g
Polyunsaturated Fat 0g
Monounsaturated Fat 0g
Total Carbohydrates 25g
Dietary Fiber 1g
Vitamin A 0%
Vitamin C 0%
Vitamin D 0%
*Percent Daily Values are based on a 2,000 calorie diet