Pumpkin Chocolate Chip Cookie Sandwiches

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 white plate

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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Close-up of a Pumpkin Chocolate Chip Cookie Sandwich
Recipe

Pumpkin Chocolate Chip Cookie Sandwiches

  • Author: Lindsay
  • Prep Time: 20 minutes
  • Cook Time: 7 minutes
  • Total Time: 27 minutes
  • Yield: 18-20 cookie sandwiches 1x
  • Category: Dessert
  • Method: Oven
  • Cuisine: American

Description

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!


Scale

Ingredients

CHOCOLATE CHIP COOKIES 

  • 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

PUMPKIN ICING

  • 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

Instructions

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.

Keywords: pumpkin chocolate chip cookies, pumpkin chocolate chip cookies recipe, pumpkin dessert recipe, easy pumpkin dessert, double chocolate chip cookies, soft chocolate chip cookies

Enjoy!

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Recipe rating

25 Comments
  1. Jennifer Lamson-LaPlume

    I made these for church refreshments along with 2 of your other recipes relating to pumpkin. These cookies flattened out. I am not sure what went wrong. They look like how my oatmeal cookies look (except for when I made you apple ones). Even though they were flat they were voted a favorite by the congregation. So we’re making them again this week.

  2. Chineka @ Savor The Baking

    Wow! These cookies look great and I bet they taste even better. I can’t wait to try them out.

  3. Suzanne @ Flour Arrangements

    These cookies are beautiful! I’ve never tried chocolate with pumpkin before, but you’ve totally convinced me!

  4. Thalia+@+butter+and+brioche

    Oh my god.. these cookie sandwiches look incredible! I especially am loving that thick layer of frosting in the middle. Craving a bite of one right now, pinned!

  5. Lindsey+@+American+Heritage+Cooking

    oh, yes this was an excellent way to use that icing!!! They look delicious! It sounds like AShville was a blast!! I’ve never been downtown either…didn’t even know it was there. I’ll have to drag my husband back so we can see it and revisit the Biltmore library too.

  6. Trish - Mom On Timeout

    Couldn’t think of a better use for that leftover frosting! These are all kinds of gorgeous! Pinned and sharing on FB today!

  7. Amy @ Amy's Healthy Baking

    I love how you baked cookies to find a use for the frosting… I would’ve just eaten it with a spoon! No shame. 😉 So glad you had fun on your retreat to Asheville! I’ve heard so many awesome things about it, but… Being on the West Coast, it’s a little bit more of a trek to get out there. But I’d love to see the Biltmore someday!

    1. lifeloveandsugar@gmail.com

      lol, I eat some on it’s own, but I’ve got to find a way to share it or I’d eat way to much sugar and sweets. 🙂

  8. Donna

    I am all over these cookie sandwiches. In fact, I want to whip them up this weekend! Will it matter whether I use instant pudding mix or cook n serve pudding mix? Also, which size — the small box or the big box?

    Many thanks!

  9. Alice @ Hip Foodie Mom

    I so want to visit Asheville, NC . . I hear it’s beautiful. . and these cookie sandwiches?!!! OH MY GAWD. . love!! the pumpkin icing is genius!

  10. Mir

    Forget your happy dance at the restaurant (though that does sound really amazing). I’m doing a happy dance right now! These look entirely too gorgeous. Most people make sandwich cookies. You elevate it to an art form!

Lindsay
About Lindsay

I'm a wife and mom to twin boys, a baby girl and a sweet black lab with a serious sweets addiction! Bring on the sugar!

Scripture I’m Loving

“Be joyful in hope, patient in affliction, faithful in prayer.” Romans 12:12