Caramel Stuffed Oatmeal Pumpkin Cookies

 Super soft and chewy Oatmeal Pumpkin Cookies stuffed with Caramel. Fall baking doesn’t get much better!


Welcome to another week! Did you have a good weekend? Mine is pretty much summarized by these cookies. Cookies are my ultimate comfort food, especially when they come with plenty of chocolate chips, caramel and the awesomeness of pumpkin. I worked hard on these, friends.

I have had my fair share of cakey pumpkin cookies, which isn’t necessarily a negative thing. While they can be just as delicious, I wanted a pumpkin cookie that tastes just like a cookie should. Complete with crispy edges, ultimate chewiness and zero disappointment.


And after perfecting THE pumpkin cookie recipe, I couldn’t help but add ooey gooey caramel to each one. I thought it couldn’t get much better, but the addition of caramel definitely stepped things up.

Once you go caramel stuffed there’s no going back. I may never make “regular” cookies again.


Even though we’re just getting started with the fall recipes, I can confidently say that if I had to choose only one thing to make this season, this recipe would be it. I could eat these cookies week after week and never grow tired of them. On the contrary, the more I eat these cookies, the harder it is to stay away from the cookie jar.


And that’s precisely the reason why.

The dough does require some chill time in the fridge before baking the cookies. It’s essential for enveloping the caramels with the dough and making sure that it doesn’t leak while baking, i.e. to avoid a caramelly mess on your baking sheets.

If you’re short on time, you could skip the caramel step (and therefore the chill time) and simply make amazing Oatmeal Pumpkin Cookies. They’re filled with chocolate chips and toffee, btw. This makes for an excellent base recipe and they’re still extremely delicious.


This is why I love fall so much. Good thing we’re just getting started, I need all the time I can get to chow down on these.


 Yep, you should most definitely give them a go! Have an amazing start to your week!

Caramel Stuffed Oatmeal Pumpkin Cookies
Yields 24
These cookies have it all. Fall into fall with these scrumptious cookies. You won't be sorry!
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  1. 1 cup (2 sticks) unsalted butter, softened
  2. 3/4 cup granulated sugar
  3. 3/4 cup brown sugar
  4. 1 large egg
  5. 1 teaspoon vanilla extract
  6. 1 cup pumpkin puree
  7. 1 teaspoon baking soda
  8. 1 teaspoon salt
  9. 1 teaspoon pumpkin pie spice
  10. 2 1/2 cups all-purpose flour
  11. 1 1/2 cups old-fashioned oats
  12. 1 cup semisweet chocolate chips
  13. 1/2 cup toffee bits
  14. 24 Rolo candies
  1. 1. In the bowl of your stand mixer, cream together butter and sugars until light and fluffy. Mix in egg, vanilla, and pumpkin. Add baking soda, salt, and pumpkin pie spice and stir until incorporated. Finally add flour and oats and stir until combined. Fold in chocolate chips and toffee bits. Cover bowl and refrigerate for 2 hours or until ready to use.
  2. 2. Line a baking sheet with parchment paper. Preheat oven to 350 degrees F and unroll Rolo candies from their wrappers. Using a large cookies scoop (about 3 tablespoons), scoop cookie dough onto prepared baking sheet. Enclose one Rolo candy with one dough ball and cover completely. Roll into a ball and return to the baking sheet. Repeat. Bake for 12-14 minutes or until lightly browned. Let cool on baking sheet for 10 minutes before moving to wire racks to cool completely.
  1. Cookies will keep up to 5 days stored in an airtight container or up to 4 weeks in the freezer.
Deliciously Yum!

24 thoughts on “Caramel Stuffed Oatmeal Pumpkin Cookies

    • Thanks, Kelly! I am glad I can send you some MN love from my blog. It looks like you’re having a great time getting acclimated to your new NYC home ;). XOXO!

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