Pumpkin Chocolate Chip Cookie Sandwiches

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These Pumpkin Chocolate Chip Cookie Sandwiches are so cute, fun and delicious! Two soft double chocolate chip cookies are sandwiched together with creamy homemade pumpkin frosting!

For another perfect pumpkin treat, don’t forget to check out my Pumpkin Cupcakes with Cream Cheese Frosting!

Pumpkin Chocolate Chip Cookie Sandwiches Stacked on a Plate

Pumpkin Chocolate Chip Cookie Sandwiches

Remember when I made this Chocolate Pumpkin Cheesecake Cake last week and said I needed to find another use for the pumpkin icing because it was so darn good? Well, I decided what to do. Sandwich it between two chocolate pudding cookies filled with chocolate chips. Pumpkin Chocolate Chip Cookie Sandwiches are where it’s at.

Asheville, NC is also where it’s at. Or at least, it’s where I’m at until later today. We’ve been on a work retreat since Tuesday – working, exploring, having a few laughs and eating entirely more than necessary.

With the exception of a few hours of work each day, we’ve been spending a lot of time on activities. Bike tours, touring the Biltmore, wearing super cool muppet shirts. We’ve had some fun.

I’ve been to Asheville before, but not the downtown area. We stayed in a place right downtown so that we can walk to most everything, which is a nice change from having to drive everywhere out in the ‘burbs.

A couple interesting things I’ve noticed about Asheville:

1. Stores open late and close early. Mostly it seems to be 10-6. On the one hand, I dig it. Seems like it’d give a good work/life balance. On the other hand, I’m not a fan. The only time I’ve had to break off and try to go into a few shops was yesterday at 6. Right when everything closed. So I checked out a bakery, French Broad Chocolates, that was recommended instead.

5 Pumpkin Chocolate Chip Cookie Sandwiches stacked on a black cake stand
A Stack of Pumpkin Chocolate Chip Cookie Sandwiches on a Plate

2. This is the most dog friendly place I have EVER BEEN! Like ever. And it’s kind of awesome. In stores, restaurants, walking around – there are dogs everywhere. There are dog bowls at many shops with water. Our hotel is even fostering a dog that hangs out in it’s little pen area in the lobby hoping someone will adopt it. Seriously, how cute is that? It’s like a little mascot. When I got up to work out the other morning, I peeked in on her and she was sleeping with a blanket over her. So cute.

3. There’s a ton of fun and different food places around. Not so many sweets, which I could use more of, but still. I enjoy a good fun and different meal and I have certainly had those while here.

My favorite has probably been the place we had dinner at last night – Curate. It’s tapas and they had one that was pork prepared like a skirt steak (called cerdo iberico a las finas hierbas – I just pointed – “that one”) and OH MY GOSH! SO good! When they brought out a second plate of it and I realized there was more, I actually did a little happy dance with some fist pumping.

Pumpkin Chocolate Chip Cookie Sandwiches on a Cake Stand

And if you like the chocolate and pumpkin flavor combo, these cookie sandwiches might just induce a happy dance as well.

There’s nothing softer, as far as cookies go, than a pudding cookie. They are just awesome. And they make a terrific cookie sandwich because they aren’t too hard to bite into, causing the icing to squeeze out. They are the perfect softness so that they keep everything held together, but perfectly blend with the icing when you bite into it.

Tips for Making These Tasty Cookie Sandwiches

Of course if you don’t have access to pudding mix, do not fear, you can still make these cookie sandwiches. Just reduce the flour to 1 1/4 cups, and use 1/2 cup total of cocoa. Keep everything else the same. They’ll still be delicious, just not as soft.

And as previously stated, the pumpkin icing is the jam. It’s the reason these cookie sandwiches came to be. The cookies are the delivery vessel for the icing. Together they make pumpkin and chocolate chip awesome sauce. You’ll want to eat it right up. 🙂

A Stack of Pumpkin Chocolate Chip Cookie Sandwiches on a plate

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Chocolate Pumpkin Cheesecake Cake
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Close-up of a Pumpkin Chocolate Chip Cookie Sandwich

Pumpkin Chocolate Chip Cookie Sandwiches

  • Author: Lindsay
  • Prep Time: 20 minutes
  • Cook Time: 7 minutes
  • Total Time: 27 minutes
  • Yield: 18-20 cookie sandwiches
  • Category: Dessert
  • Method: Oven
  • Cuisine: American


These Pumpkin Chocolate Chip Cookie Sandwiches are so cute, fun and delicious! Two soft double chocolate chip cookies are sandwiched together with creamy homemade pumpkin frosting!



  • 3/4 cup salted butter, room temperature
  • 3/4 cup sugar
  • 1/4 cup brown sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 2 cups all purpose flour
  • 2 tsp cornstarch
  • 1 tsp baking soda
  • 1 3.4oz package dry instant chocolate pudding mix
  • 2 tbsp cocoa powder
  • 1/2 cup chocolate chips
  • 23 tsp milk


  • 1/2 cup butter
  • 1/2 cup shortening
  • 4 cups powdered sugar
  • 1/4 cup pumpkin puree + 2 tbsp
  • 3/4 tsp pumpkin pie spice


1. Preheat oven to 350 degrees.
2. Cream butter and sugars together until light and fluffy, about 3-4 minutes.
3. Mix in egg and vanilla extract.
4. With the mixer on low speed, add flour, cornstarch, baking soda, dry pudding mix and cocoa powder.
5. Stir in chocolate chips. Add milk, if needed. Dough will be thick.
6. Make balls of about 1 tbsp and then flatten a bit into thick discs and place on cookie sheet. They will spread a little while they bake.
7. Bake for about 7-8 minutes.
8. Remove from oven and allow to cool for 2-3 minutes on cookie sheet, then transfer to cooling rack to cool completely.
9. While cookies cool, make icing. Beat the shortening and butter until smooth.
10. Slowly add 3 cups of powdered sugar. Mix until combined.
11. Mix in the pumpkin puree and pumpkin pie spice.
12. Add the rest of the powdered sugar and mix until smooth. Add more water until it’s the right consistency.
13. Once cookies are cool, make cookie sandwiches.


  • Serving Size: 1 Cookie Sandwich
  • Calories: 375
  • Sugar: 32.2 g
  • Sodium: 207.2 mg
  • Fat: 19.6 g
  • Carbohydrates: 48.8 g
  • Protein: 3.2 g
  • Cholesterol: 43 mg

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About Lindsay

I'm a wife and a mom to twin boys and a baby girl! And I've got a serious sweets addiction! Bring on the treats!

Scripture I’m Loving

“Come to me, all you who are weary and burdened, and I will give you rest. Take my yoke upon you and learn from me, for I am gentle and humble in heart, and you will find rest for your souls.” Matthew 11:28-29