Roll and Cut Oatmeal Cookies with Pumpkin Filling

| cookies, filled cookies, oatmeal, pumpkin cookies, recipes, rolled cookies

Soft and chewy oatmeal & molasses cookies filled with sweet pumpkin and topped with a sugary crunch, these cookies are uniquely amazing!

Roll and Cut Oatmeal Cookies with Pumpkin Filling |

I think Betty Crocker was on to something with these cookies.  I’ve never seen, tasted or made anything quite like these roll and cut oatmeal cookies with pumpkin filling before.  The recipe comes from my favorite cookie cookbook…  Betty Crocker’s Cooky Book circa 1963.  I’ve made cookies from this book so many times, I’ve even blogged about this book before… but the recipes I’ve made have been ones I grew making, the recipes my Mom loved.

Not this time.

This time I took an adventure and I looked on every page of this cookbook until I found a cookie recipe that fit the current season in appearance and flavor… and more importantly I wanted something unique.  A cookie I had never seen before on Pinterest or other blogs. Roll and Cut Oatmeal Cookies with Pumpkin Filling | I’m certain I found just that with these cookies.  These cookies are so unique, they jumped off the page when I saw them in the book. What makes these cookies unique are that they’re a rolled and cut cookie AND they’re filled! Woah.  Rolled and cut oatmeal cookie dough?

Yup.  You read that correctly.

Have you ever rolled and cut oatmeal cookie dough before?  Because I certainly haven’t.  Surprisingly, this dough rolled very easily,  just needed a lot of flour on the counter so it didn’t stick. Roll and Cut Oatmeal Cookies with Pumpkin Filling | The original recipe didn’t call for this, but I topped the cookies with a sprinkling of Sugar in the Raw to add a sweet crunch to the cookie.  It turned out to be the perfect addition to the recipe and really rounded out the flavors and textures.

These roll and cut oatmeal cookies with pumpkin filling are sure to WOW and impress your family and friends with their unique shape and appearance and their flavor.

Try them, you won’t be disappointed!


Roll and Cut Oatmeal Cookies with Pumpkin Filling
Prep time

Cook time


Serves: 18-20 cookies

  • 2 cups all-purpose flour
  • 1 tsp salt
  • ½ tsp baking soda
  • ½ cup light brown sugar, packed
  • ¾ cup shortening, cubed
  • 1 egg
  • ¼ cup molasses
  • 1 cup quick oats
  • ¼ cup Sugar in the Raw, for garnish
Pumpkin Filling
  • 1 cup pumpkin puree (NOT pumpkin pie mix)
  • ½ cup sugar
  • 1 tsp pumpkin pie spice

Pumpkin Filling
  1. In a bowl, whisk together the pumpkin puree, sugar and pumpkin pie spice.
  1. Preheat oven to 375 F degrees. Line cookie sheet with parchment paper.
  2. In the bowl of your stand mixer, combine the flour, salt and baking soda.
  3. Add the cubed shortening and mix on medium speed until the dough has a coarse meal consistency.
  4. Mix in the sugar, egg and molasses until combined. Scrape the sides of the bowl to make sure everything has been incorporated.
  5. Add the oats and mix until evenly distributed.
  6. Roll dough out ⅛” thick onto a lightly floured board. Cut with 2⅝” round cutter. Place half the rounds on the prepared cookie sheet.
  7. Put 1 heaping teaspoon of pumpkin pie filling in the center of each round on the cookie sheet and spread just to the edges. NOTE: You do not want the filling to go to the edges or off the side.
  8. Using a small star cutter, cut the center of the remaining discs out. Place the cut disc on top of a filled disc on the prepared cookie sheet.
  9. Using your index finger, press the edges closed to seal.
  10. Brush a very light layer of water onto each cookie and sprinkle Sugar in the Raw over just the dough, not the filling. The water will help the sugar stick to the dough.
  11. Bake for 11-13 minutes or until the bottom edges and tops begin to turn golden brown. At about 11 minutes, gently lift up one of the cookies and check the bottom… if it’s golden, they are done.
  12. Immediately remove the cookies to a wire rack to cool.
  1. The cookies are hard the first day and are great to dunk in tea. They will be come softer and actually taste better on day 2.
  2. Store in an air tight container for up to 4 days.

Original recipe from Betty Crocker’s Cooky Book.


5 Comments on Roll and Cut Oatmeal Cookies with Pumpkin Filling

  1. grandbabycakes
    November 14, 2013 at 3:36 pm (1 year ago)

    Those are beautiful and fun cookies! I am so glad we got each other in the blogger cookie exchange.

    • Betsy Eves
      November 15, 2013 at 10:00 am (1 year ago)

      Thank you! I’m excited! I can’t wait to BAKE! <3

  2. Mallory @ Total Noms
    November 16, 2013 at 2:02 am (1 year ago)

    I have never seen cookies like this before! They look like cute little hand pies!

    • Betsy Eves
      November 16, 2013 at 11:22 am (1 year ago)

      I hadn’t either. But they were SO GOOD! Especially the second day when the pumpkin soaked into the cookie and they got soft. PERFECT with coffee or tea! YUM!


1Pingbacks & Trackbacks on Roll and Cut Oatmeal Cookies with Pumpkin Filling

  1. […] Rolled & Cut Oatmeal Cookies with Pumpkin Filling […]

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>

Rate this recipe: