These Pumpkin Spice Oatmeal Thumbprint Cookies with Date Caramel feature pumpkin spiced oatmeal cookies made with oat flour and quick oats, real pumpkin puree, and sweetened with coconut sugar and filled with an easy 3-ingredient date caramel for the perfect Fall-flavored cookie that’s naturally sweetened, gluten-free, and vegan!

Thumbprint cookies were one of my favorite holiday traditions growing up. My parents would make them every year at Christmas time and the recipe has been passed down through the generations. I love the simplicity of the cookie dough, and that they don’t take very long to bake. Luckily they are easily made gluten-free and vegan as well, so I can keep the tradition going. 🥹

Although typically we put jam in the middle of these oatmeal thumbprint cookies, I started experimenting with different fillings in the middle. In my baking book, The Beginner’s Guide To Gluten-Free Vegan Baking, I created a Turtle Thumbprint cookie. For the holidays last year I created these Oatmeal Gingerbread Thumbprint Cookies with White Chocolate Nog Ganache which are soooo good! And because we all go crazy over pumpkin spice when Fall rolls around, I thought I’d make these Pumpkin Spice Oatmeal Thumbprint Cookies with Date Caramel to fit the season. 🎃

The Pumpkin Spice Oatmeal Cookie Ingredients

As I mentioned, the oatmeal cookie dough is really simple to make. Here’s what you’ll need:

Vegan butter. My go-to butter brand is Miyoko’s. I like the European Style Cultured Vegan Butter Block for these cookies.

Coconut sugar. To keep these cookies naturally sweetened without the use of refined sugars, I am using coconut sugar. Don’t worry, if you’re not a coconut lover, they don’t give these cookies a coconut flavor.

Pumpkin puree. You’ll need a can of pure pumpkin puree for these cookies. Not pumpkin pie mix.

Pure vanilla extract. Make sure it’s pure and NOT imitation vanilla, which is not gluten-free.

Oat flour. Be sure to use gluten-free oat flour. I used Bob’s Red Mill.

Pumpkin pie spice. I use Spice Islands Pumpkin Pie Spice, but you can use another brand or certainly make your own pumpkin spice blend.

Cinnamon. There is probably cinnamon in the pumpkin pie spice, but you’ll be adding an additional 1/2 teaspoon of ground cinnamon. Trust me… 👌🏻

Baking soda. Baking soda helps the cookies to spread a little when baking.

Salt. Helps to bring out the sweetness of the cookies and compliments the caramel so well.

Plant milk. I used oat milk, but you can use whatever plant milk you like… almond, soy, coconut, etc.

Quick oats. Make sure you use gluten-free quick oats. I used the One Degree Organics sprouted, glyphosate free quick oats.

Preheat the oven to 350 degrees F. Beat the butter until smooth, then add the sugar and molasses, beat until well combined. In a separate bowl combine the oat flour, pumpkin pie spice, cinnamon, baking soda, and salt and then slowly add it to the butter mixture beating it until well combined. Turn the beater/mixer off, and stir in the plant milk and quick oats. Using a cookie scoop (I used a D24 approximately 2 tablespoons) scoop the cookie dough and then roll them into balls. Place them two inches apart on a parchment-lined baking sheet.

Next, press down in the center of each cookie with your thumb or the back of a measuring spoon and bake for 10-12 minutes, 10 minutes if you like softer cookies, 12 if you like a bit crunchier of a cookie. Remove from the oven and let them cool. You may need to gently press the center down again with the back of a measuring spoon to ensure the well is deep enough to fill.

The Date Caramel Filling

While the cookies are baking and cooling, make the date caramel. This date caramel is also super simple to make with just 3 ingredients. I have a whole separate blog post on this 3-Ingredient Vanilla Date Caramel because it was so popular on Instagram!

You will need 10 large medjool dates, 1/4 cup of coconut cream (the solid part of a can of coconut milk) and 1 teaspoon of pure vanilla extract.

Pit the dates and add them to a microwave safe bowl/measuring cup. Cover with water and microwave for 2 minutes. Drain and add to a food processor or high speed blender. Add the vanilla and coconut cream and blend until til smooth, stopping to scrape down the sides, until creamy. Set aside.

Once the cookies are completely cool, gently spoon some of the date caramel into the middle of each cookie. Store leftover cookies covered on your counter for up to 3 days.

If you’re a pumpkin spice lover, an oatmeal cookie lover, a caramel lover- I think these cookies check all the boxes! 🤗 Be sure to check out the video in this post to see how easy it is to make these delicious cookies!

Let me know how you like these Pumpkin Spice Oatmeal Thumbprint Cookies with Date Caramel down below in the comments section, as well as giving it a rating ⭐️⭐️⭐️⭐️⭐️ so that others can discover this delicious Fall cookie recipe! Tag me on Instagram, Facebook, or save for later on Pinterest!