Oct 232016

These chewy, decadent chocolate chip cookies are filled with an autumn surprise – creamy, rich pumpkin cheesecake.


I know I’ve said it before, but fall in Upstate NY is awesome (and you’ll never hear any good things from me about the winter, so some extra fall love is warranted).  The crisp autumn air is refreshing and the gorgeous changing leaves are one-of-a-kind, and there is no better way to experience the richness and colors of the season than by going on a wine tour.

Picture yourself in a limo bus, surrounded by some of your closest friends, ample amounts of cheese and crackers, and supplemental road beverages, as you cruise around one of the Finger Lakes from winery to winery.  The tour I went on yesterday was a one-year pre-celebration for my husband’s brother and one of my closest friends, who are getting married in October 2015 at one of the vineyards that we visited yesterday. They planned a perfect itinerary that included stops at a complex with 3 wineries and a brewery, a hippie-themed winery with vintage concert posters, eclectic memorabilia, and wines named after famous classic rock songs, and of course, the site of next year’s wedding, where we sampled wines and beers that they will be able to choose for the open bar during the reception.

The view from their wedding winery is absolutely stunning, and this shot from yesterday should be indicative of what we’ll be seeing next year.

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I’ve been so into the fall this year, and in addition to this wine tour and another that I’m going to on Saturday, I have been on a huge pumpkin baking kick. I decided to formulate these pumpkin cheesecake-filled chocolate chip cookies because they combine two of my all-time favorite desserts and there’s really nothing like them out there.  They are incredibly simple and turn out amazing.

I’m sure you’re wondering how I got the cheesecake INTO the cookies.  There are plenty of pumpkin cheesecake chocolate chip cookie BAR recipes out in internet land that require you to pour cheesecake batter over a layer of cookie dough, but I wanted to figure out a way to get the cheesecake into a cookie. After a logistical trial and error fail (that my employees generously reaped the yummy benefits of), I devised a fool-proof way to keep the cheesecake filling whole, intact, and well-shaped inside of the cookie by using a regular household item:

An ice cube tray!


After you prepare the cheesecake filling, pour about 1 to 1 ½ teaspoons into each ice cube tray slot until you’ve used all of the batter. Then, freeze the trays for at least an hour to set the cheesecake.  The shape and support of each tray slot leaves you with a perfectly-sized cheesecake cube that will bake perfectly inside your cookies.

Your cheesecake filling has chilled at least an hour, and you’ve prepared your cookie dough.  Remove the ice cube trays from the freezer, and squeeze and rotate the first tray from both ends to loosen the cubes of filling. Be careful: the filling is much thicker than regular ice cubes, and I actually broke an ice cube tray in half by squeezing too hard. Parts of the tray and cheesecake cubes hit the kitchen floor, a cat, and my face before the ordeal was done. I don’t recommend that you try that at home.

Once the cubes are loosened, scoop out a generous portion of cookie dough with your hands. Pull one cube of filling out of an ice cube tray slot and press it directly into the cookie dough. Add more dough, if needed, to be able to roll a full circle of dough around the cube, making sure that no cheesecake filling is visible through the dough. Depending on the shape of your ice cube trays and the size that you make your cookies, you may be left with a few extra cubes of filling. Transfer them to the fridge and eat them with small dollops of whipped cream for a mini dessert treat.

Place your cookies 2 inches apart on a baking sheet and bake at 350 degrees for 11-12 minutes. You want the edges of the cookies to be just starting to turn golden brown. Since these cookies have to be refrigerated, undercooking them just a little will help maintain their chewiness.  You will be left with 18-24 huge, delicious chocolate chip cookies with just the right amount of pumpkin cheesecake filling baked right into the middle.

These cookies can be stored in the fridge for up to 3 days, but I guarantee you they won’t last that long.

Pumpkin Cheesecake-Filled Chocolate Chip Cookies
Prep time
Cook time
Total time
These chewy, decadent chocolate chip cookies are filled with a surprise - creamy, rich pumpkin cheesecake.
Recipe type: Dessert
Serves: 24
  • ¼ c. cream cheese, softened
  • ¼ c. sugar
  • ¼ c. canned pumpkin
  • ¼ tsp. pumpkin pie spice
  • 1 egg

  • 1 c. (2 sticks) butter, softened
  • 1 c. brown sugar
  • 2 eggs
  • 1 tbsp. vanilla
  • ¼ c. canned pumpkin
  • 1 tsp. baking soda
  • 1 tsp. salt
  • 2¾ c. flour
  • 2 c. semi-sweet chocolate chips
  1. Prepare the cheesecake filling by beating the cream cheese with an electric mixer for 1-2 minutes or until whipped.
  2. Add sugar, canned pumpkin, pumpkin pie spice, and egg. and beat with mixer until completely smooth.
  3. Spray 2 ice cube trays with non-stick cooking spray.
  4. Fill each slot of the ice cube trays with 1 to 1½ teaspoons of cheesecake filling until you've used all of the filling.
  5. Freeze the ice cube trays for at least one hour or up to overnight to set the cheesecake.
  6. To prepare the cookies, cream the softened butter and brown sugar with an electric mixer for 2-3 minutes.
  7. Add the eggs, vanilla, and canned pumpkin and continue to beat until smooth.
  8. Stir in baking soda, salt, and flour until combined.
  9. Fold in chocolate chips until evenly distributed.
  10. Preheat oven to 350 degrees.
  11. Remove ice cube trays of cheesecake filling from the freezer.
  12. Remove one slot of cheesecake filling from the ice cube tray. Then, using your hands, scoop out some cookie dough and press the cube of cheesecake filling into the center of the dough.
  13. Add more dough (if needed) to cover the entire cube of cheesecake filling, and then roll the dough to create a circle. Repeat with remaining cubes until you've exhausted all of the cookie dough.
  14. Place cookies 2 inches apart on a cookie sheet.
  15. Bake cookies at 350 degrees for 11-12 minutes or just until the outside edges start to turn golden.
  16. Cool cookies for 20 minutes on the baking sheet for them to firm up, and then transfer to a wire rack to cool completely.
  17. Store cookies in refrigerator in an airtight container for up to 3 days. The cookies are best enjoyed cold, right out of the fridge!
  18. Yields 18-24 very large cookies.

  2 Responses to “Pumpkin Cheesecake-Filled Chocolate Chip Cookies”

  1. I love your story on here – sounds like Sean & Maggie’s wedding location will be awesome. Your dad goes on and on about the changing of the colors out there in the fall – love the way you describe it too. I am so proud of you doing this. Wish I was closer to taste more of your cooking! Love you bunches and bunches……..

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