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You are here: Home / Cookies / Pumpkin Chocolate Chip Pillow Cookies

Pumpkin Chocolate Chip Pillow Cookies

October 8, 2014 by Wendy Sondov 29 Comments

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This week, the Cookie Month ’14 bloggers are sharing recipes for cookies that are their family favorites. My contribution is Pumpkin Chocolate Chip Pillow Cookies, with options for white flour, whole wheat, and gluten free versions.

Pumpkin Chocolate Chip Pillow Cookies (gluten free option) #cookiemonth14

At this moment, I have an absurd amount of flour in my kitchen. There may be more than forty pounds. Absurd even for a baking blogger. My canisters were already filled with a variety of flours (all-purpose, bread, cake, self-rising) when my Cookie Month goodies arrived from Bob’s Red Mill.

Pumpkin Chocolate Chip Cookies

The supportive folks at Bob’s sent me 15 pounds of flour to play with, as I tried out Cookie Month recipes. The bags contained unbleached all-purpose organic flour, whole wheat organic flour, and 1-to-1 Gluten Free Baking Flour.

flour

My gluten sensitive daughter was especially excited about the wheat free baking flour. She gets a little frustrated not being able to taste test my baking endeavors. My objective was a recipe in which any of the three types of flour could be used interchangeably. I was hoping for a recipe that produced delicious cookies with any of the flours, not necessarily the same taste with each flour, but delicious regardless of which flour was used. I did not have instant success. Maybe I am overly picky (my daughter says I am), but I wasn’t happy with the texture of several recipes I tried. The gluten free honey cake was tasty but rubbery. The gluten free gingerbread cookies were a little dry and grainy. Finally, not being able to resist the seasonal pull of pumpkin, I tried the flours in one of our family favorites, Pumpkin Chocolate Chip Pillow Cookies. Bingo!

Pumpkin Chocolate Chip Cookies

I am attributing the versatility of this recipe to the high moisture content of the pumpkin puree. All three versions of Pumpkin Chocolate Chip Pillow Cookies are moist and soft, like little round chocolate coated bites of cake. The taste and texture of all three versions is so similar that you could sneak some nutritious whole wheat into your cookie jar and no one would know, or you could serve a gluten free cookie that everyone would enjoy.

Pumpkin Chocolate Chip Pillow Cookies (gluten free option) #cookiemonth14

I used dark Bada Bing Bada Boom Dipping and Coating Formula from Chocoley.com to drizzle or coat the cookies. I really like using these little chocolate discs. They taste like real chocolate because they are real chocolate. Bonus, they are gluten free. The dipping and coating formula is a compound chocolate. It doesn’t require tempering and melts to the perfect pouring consistency. Drizzling melted chocolate over the cookies is fast and creates a pretty cookie. Coating the tops of the cookies in chocolate takes a little longer (and requires more chocolate), but in addition to tasting great and looking irresistible, I think being coated helps the cookies retain their moisture and stay fresh longer.

Pumpkin Chocolate Chip Pillow Cookies (gluten free option) #cookiemonth14Pumpkin Chocolate Chip Cookies

Though this recipe makes a LOT of little cookies(60), they are each only one or two bites. It is way too easy to eat numerous Pumpkin Chocolate Chip Pillow Cookies at a time. You will be glad the recipe makes a lot.

Pumpkin Chocolate Chip Pillow Cookies (gluten free option) #cookiemonth14

Care package shipping note: These cookies stay fresh for at least 5-7 days, but should only be shipped in cool/cold weather. Warm temperatures can melt the chocolate and cause the moist cookie to mold.

Pumpkin Chocolate Chip Pillow Cookies (gluten free option) #cookiemonth14

Pumpkin Chocolate Chip Pillow Cookies (gluten free option) #cookiemonth14
Print

Pumpkin Chocolate Chip Pillow Cookies

Adapted from Nestle’s Very Best Baking
Makes 5 dozen cookies
Author Wendy Sondov themondaybox.com

Ingredients

  • 2 ¼ cups all-purpose whole wheat, or Bob’s Red Mill Gluten Free Baking Flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ¼ teaspoon salt
  • 2 ½ teaspoons cinnamon
  • 1 cup unsalted butter room temperature
  • ½ cup granulated sugar
  • ½ cup brown sugar packed
  • 1 15 ounce can pumpkin puree
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 2 cups semi-sweet chocolate chips
  • For decorating:
  • 4 cups dark semi-sweet, or milk chocolate chips (I use Bada Bing Bada Boom Dipping and Coating Formula)
  • sprinkles

Directions

  1. Preheat oven to 375˚F. Line a baking sheet with parchment paper.
  2. In a medium bowl, whisk together flour, baking powder, baking soda, salt, and cinnamon.
  3. In the bowl of an electric mixer, cream together butter and sugars. Beat in pumpkin, eggs and vanilla until incorporated.
  4. Gradually add flour mixture.
  5. Stir in chocolate chips.
  6. Scoop rounded tablespoon balls of dough onto prepared baking sheet, 2” apart.
  7. Bake for about 15 minutes or until the bottom edges are lightly browned.
  8. Cool for 5-10 minutes on the baking sheet before placing on a wire rack to cool completely.
  9. Decorating: Once completely cool, cookies can be drizzled or coated in melted chocolate. Melt the chocolate over a double boiler or in a microwave at 50% power.
  10. To drizzle, place cookies on a baking sheet lined with wax paper. Using a spoon or fork drizzle melted chocolate over cookies. Top with sprinkles while the chocolate is still wet. To coat, place cookies on a wire rack positioned over a wax paper lined baking sheet. Spoon melted chocolate over cookies. Top with sprinkles while the chocolate is still wet.
  11. Place the baking sheet of drizzled/coated cookies in the refrigerator for 5-10 minutes until the chocolate is set.
  12. Store cookies for 5-7 days in an airtight container at room temperature with wax paper between layers.

Packing Tips

Pumpkin Chocolate Chip Pillow Cookies should be mailed only in cool/cold weather care packages. In warm weather the chocolate coating will melt and the high moisture in the cookie would promote mold. For shipping, double wrap pairs of cookies (with bottoms together) in plastic wrap, then place in an airtight container.

Pumpkin Chocolate Chip Pillow Cookies

 

**This post is sponsored by Bob’s Red Mill. They are one of our Cookie Month sponsors, partnering with us to create delicious cookie recipes for you to enjoy. Chocoley.com  provided their dark chocolate Bada Bing Bada Boom Dipping and Coating Formula  for use in this recipe. **

Be sure to check out my Cookie Month partners and their amazing recipes: Jess at The 104 Homestead – Kathie at Homespun Seasonal Living – Tessa at Homestead Lady – Chris at Joybilee Farm – Sheila at Life, Love, and Good Food – Nikki at Nik Snacks – Shari at Pure Grace Farms – Angi at Schneiderpeeps – Lauren at Wicked Spatula

The following companies generously sponsored this and other cookie month projects. I may not have used all of them in my recipes, but this project is in no small part thanks to them and their incredible contributions: Bob’s Red Mill, The Daily Meal, India Tree, KerryGold, King Arthur Flour, Products of GIR, KaTom, SunButter & Wilton.

You might also like:

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Filed Under: Cookies Tagged With: #cookiemonth14, Bob's Red Mill, cakey cookie, care packages, Chocoley.com, gluten free, military care packages, Pumpkin Chocolate Chip Cookies, whole wheat

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Comments

  1. Monica says

    October 8, 2014 at 12:24 pm

    I love this experiment of yours, Wendy! I totally agree – sometimes it’s a matter of using different flours for different recipes and, unfortunately, we can’t just interchange randomly. It’s interesting (and makes sense) that the moisture from the pumpkin puree was probably key here. These cookies look wonderful and it’s so great to be able to use those different types of flours for the same tasty result. And I’m a fan of Bob’s Red Mill – enjoy your flours! It’ll come in handy for the holiday baking season. : )

    Reply
    • themondaybox says

      October 10, 2014 at 9:53 am

      Thanks, Monica! I really have been like a kid in a sandbox, playing with all of that flour (not to infringe on your blog title!) My daughter has tried a lot of commercially produced gluten free products and as a result is less bothered by the difference in texture that gluten free baking can produce. I was looking for something that would taste “normal” even with gluten free flour. You are so right. We can’t interchange flours randomly. I wish I knew the true chemical culinary secret, but without that info all I can do is play and experiment. At least I am having fun!

      Reply
  2. Ashley says

    October 8, 2014 at 7:32 pm

    Whoa that is a lot of flour! But so cool! And these cookies look fantastic! I’m all about the pumpkin / chocolate combo – it’s such a good one!

    Reply
    • themondaybox says

      October 10, 2014 at 9:47 am

      Thanks, Ashley! Even scarier than the amount of flour I started with (and don’t even look in my chocolate chip cabinet!!), is the fact that I am baking my way through all of that flour! 🙂 My husband’s employees (the recipients of much of my baking experiments) are demanding gym memberships as part of their salary package!

      Reply
  3. Pure Grace Farms says

    October 9, 2014 at 10:21 am

    Love the tutorial and the option of different types of flour. You can’t go wrong with Bob’s Red Mill. btw the cookies look fantastic.
    Blessings,
    Shari

    Reply
    • themondaybox says

      October 10, 2014 at 9:44 am

      Thanks, Shari! I was amazed that all three flours tasted equally wonderful in this recipe! Chocolate covered wonderful! 🙂

      Reply
  4. Angi @ SchneiderPeeps says

    October 10, 2014 at 9:34 am

    These look wonderful! One thing I’m excited about cookie month is finding some sweets that I can confidently make for guests who are gluten free. I’ve always struggled with that.

    Reply
    • themondaybox says

      October 10, 2014 at 9:43 am

      Thanks, Angi! Living with my gluten sensitive daughter, I am excited about finding recipes for sweets that taste so good, you can make gluten free for everyone. Making separate of everything is too time consuming!!

      Reply
  5. Melissa Ringstaff says

    October 10, 2014 at 9:51 am

    Looks delicious!

    Reply
    • themondaybox says

      October 10, 2014 at 9:57 am

      Thanks, Melissa!

      Reply
  6. Erin says

    October 10, 2014 at 10:46 am

    Oh my goodness these look GOOD! My kids would be over the moon excited about these…. hmmm. Perhaps I know our plans for the weekend?

    Reply
    • themondaybox says

      October 10, 2014 at 11:11 am

      Thanks, Erin! Be prepared to eat the whole batch in one sitting! But pumpkin is a veggie so its ok. 😉

      Reply
  7. selfproclaimedfoodie2014 says

    October 10, 2014 at 12:06 pm

    These look fantastic! I can’t wait to make them for my kids. Who doesn’t love pumpkin and chocolate?!?

    Reply
    • themondaybox says

      October 10, 2014 at 12:09 pm

      Thanks, Krissy! They were fun to make and even more fun to eat! I hope your kids love them!

      Reply
  8. bree west says

    October 10, 2014 at 1:04 pm

    15 lbs of flour!! That’s crazy, I’m jealous of everyone who’s getting to try all the treats you’ll be making! These look so good, I’m going to have to give them a try, I’m a total sucker for the pumpkin and chocolate combo!

    Reply
    • themondaybox says

      October 10, 2014 at 1:55 pm

      Thanks, Bree! The most crazy part is that I am baking enough to use it all up! A care package here, a care package there and before you know it dozens of cookies have made their way out the door. 🙂 These pumpkin cookies were a big hit once they reached their care package recipients!

      Reply
  9. Candi Elm says

    October 10, 2014 at 8:24 pm

    What a fun recipe, I love anything pumpkin and these look so good.

    Reply
    • themondaybox says

      October 10, 2014 at 8:40 pm

      Thanks, Candi! The chocolate and pumpkin are a great combination!

      Reply
  10. chrisscheuer says

    October 12, 2014 at 4:17 pm

    These are so cheerful looking Wendy. They made me smile at the first look. And it’s wonderful that you found a recipe that will work well and have great results with all these different types of flour. BRAVO!

    Reply
    • themondaybox says

      October 16, 2014 at 7:29 pm

      Thanks, Chris! I think the sprinkles definitely added some cheer to these. Working with chocolate is always a work in progress for me, but I take it as a kitchen challenge. 🙂 There is so much chemistry in baking that I still don’t understand. So my flour experiments were a learning experience!

      Reply
  11. shannon says

    October 13, 2014 at 7:10 am

    i love your comparison chart for these cookies! always interesting to see how different types of flour work in the same recipe (at least to geeks like me). 🙂 love these little cookies, too.

    Reply
    • themondaybox says

      October 16, 2014 at 7:24 pm

      Thank you, Shannon, but no one does a chart quite as artistically as you! Your pie charts are a thing of wonder. 🙂 Truthfully, I was amazed that all three versions of this cookie were almost indistinguishable! Good for those trying to use whole grains and good for those who are gluten free.

      Reply
  12. Lysha @ Magnolia Mom says

    October 13, 2014 at 10:57 am

    These look really good and super cute for fall! Pinning!

    Reply
    • themondaybox says

      October 16, 2014 at 7:21 pm

      Thank you, Lysha for the kind words and for the pin! Pumpkin tastes like fall to me. These cookies are chocolate covered fall!

      Reply
  13. April J Harris says

    November 14, 2016 at 9:03 am

    How lovely to have 15 pounds of flour to play with – especially from Bob’s Red Mill! Love these Pumpkin Chocolate Chip Cookies – as well as the variety of different ways you have glazed them. Pinned! Thank you for sharing with us at Hearth and Soul.

    Reply
    • April J Harris says

      September 25, 2017 at 7:07 am

      Sharing on the Hearth and Soul Facebook page today, Wendy 🙂 I’ve also pinned these again. I’m so pleased to see how similar the results of the versions of the recipe are, even with the different types of flour. This is definitely a keeper 🙂 Thank you so much for your support of the Hearth and Soul Link Party!

      Reply
      • The Monday Box says

        September 25, 2017 at 9:24 pm

        Oh my, April! I have been enjoying Hearth and Soul for over a year! Thank you for all of your kindness; hosting, pinning, and your sweet comments! Have a great week!

        Reply
  14. Sue from Sizzling Towards 60 & Beyond says

    September 25, 2017 at 1:23 am

    I’ve just done a boxing workout and could eat the whole plate of these cookies! Of course, I would then undo all my hard work in exercising LOL:) Thanks for sharing with us at #overthemoon link party.

    Reply
    • The Monday Box says

      September 25, 2017 at 9:21 pm

      Good for you, Sue! Don’t you dare undo all that hard work!! I suggest 1 cookie as a reward and the rest you can use to reward others. 😉 Thank you for hosting Over the Moon!

      Reply

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