This weekend B.O.B. Bob and I really got to celebrate the end of summer in style, first by attending an over-the-top Oktoberfest thrown by some of our Herndon neighbors, and then by going to see Colbie Caillat perform a concert at Wolf Trap. Smashed in between of all of that fun, there were cookies baked, Halloween decorations dragged down from the hot-as-hell attic, and a cat wrestled down to the ground to switch out her collar to one more appropriate for the upcoming season. With all of that fun, I would have to say that nothing was more enjoyable that baking cookies with reluctant assistance from B.O.B. Bob. Turns out that he makes a much better sous chef than Brenna, and he’s pretty good at dropping dough onto cookie sheets with the aid of a scoop, at least until he burns himself on the Silpat. He also got a cheap thrill out of using the mojito muddler to make indentations in the cookies for the cream cheese filling, but that’s probably because he’s a man, and it was kind of like using a tool. Perhaps next time I should let him use the head of a hammer to make it more fun.
- 1 (15-oz.) Can Pure Pumpkin
- 1 1/3 Cups Canola Oil
- 4 Eggs
- 2 Tablespoons Vanilla
- 2 Cups Light Brown Sugar, Packed
- 1 Teaspoon Salt
- 4 Cups All-Purpose Flour
- 2 Teaspoons Baking Powder
- 2 Teaspoons Baking Soda
- 3 Teaspoons Ground Cinnamon
- 1 (10-oz.) Package Mini Semi-Sweet Chocolate Baking Chips
- 1 (8-oz.) Package Cream Cheese, Room Temperature
- 1/2 Cup Unsalted Butter, Room Temperature
- 1 Teaspoon Vanilla
- 2 Cups Powdered Sugar
- Dark Cocoa Organic Cane Sugar (Optional)
- Preheat oven to 375 degrees.
- Mix the pumpkin, oil, eggs, vanilla, brown sugar, and salt together on low-speed for 3 minutes.
- While the pumpkin mixture is mixing, sift together the flour, baking powder, baking soda, and cinnamon.
- Slowly add the flour mixture to the pumpkin mixture on low-speed, and mix until just incorporated.
- Fold the mini chocolate chips into the dough until evenly distributed.
- Drop the dough onto a Silpat or parchment paper lined baking sheet with a cookie scoop or tablespoon.
- Bake for 6 minutes, remove from oven, and immediately place a well into each cookie with your thumb or the back of a tablespoon.
- Allow the cookies to cool for 2 minutes, before removing them to a cookie rack to finish cooling completely.
- Cream the cream cheese and butter together on low-speed for 1 minute.
- Add the vanilla, and then mix for an additional 30 seconds.
- On low-speed, slowly add the powdered sugar, and mix until smooth.
- Fill a large plastic Ziploc or decorating bag with filling, and then evenly distribute it among the cooled cookies. Decorate with a sprinkle of cocoa sugar.
- I use a mojito muddler to place thumbprint wells in my cookies. Look around your kitchen for any object a little under the size of a quarter; measuring spoons are usually perfect for this task.
- You can purchase Dark Cocoa Organic Cane Sugar at Seasons Olive Oil & Vinegar Taproom. There three locations are in Bethlehem, PA, Annapolis, MD, and Lancaster, PA.
- Replace the cocoa sugar with unsweetened cocoa powder or shaved chocolate.
- This recipe will yield between six or seven dozen cookies. The cookies will be moist, and will last a day or two at most, so share them with everyone around you and wish them a happy fall.
- Replace the chocolate chips with toffee bits.
- Fill the thumbprint cookies with salted caramel.
RECIPE ADAPTED FROM: Pumpkin Thumbprints from Food Network Magazine
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