When I was younger, I always thought that a cookie without chocolate chips was a lost opportunity. Even worse – cookies with raisins instead of chocolate chips! But, as I aged and grew wiser I came to realize how much I adored oatmeal cookies sans chocolate. I also developed a love of date squares (partly because they remind me of my dad). So why not combine these delicious treats for the ultimate cookie? I present you with vegan and gluten-free Oatmeal Date Sandwich Cookies. Mmm.

Picture of Oatmeal Date Sandwich Cookies, vegan and gluten-free

To all my Canadian friends, I hope you had a nice long weekend and ate delicious vegan food! In Manitoba, where I live, there was a really bad winter storm over Thanksgiving weekend. I love a good and cozy winter storm, but this one was terrible. Tens of thousands of people lost power — and some still don’t have power! The damage was also significant. We lost so many trees. I have never seen anything quite like it, and I think it’s only a sign of what’s to come. 

Picture of Oatmeal Date Sandwich Cookies, vegan and gluten-free

Oatmeal Date Sandwich Cookies

The Oatmeal Cookies

The oatmeal cookie used in this recipe is loosely based off my very popular Crispy Maple Oatmeal Cookies. I cut the sweetness of the cookies in half so that the sweetness from the dates could really shine through. I also removed the maple flakes and the coconut, but I have no doubt in my mind that these would still be lovely additions! The cookies are crunchy, but that’s done so they don’t get too soft overtime. 

Picture of Oatmeal Date Sandwich Cookies, vegan and gluten-free

The Date Filling

To amp up the date filling, I decided to cook my dates in bourbon. I love the smell of bourbon and cinnamon in the Fall. The addition of the orange juice and zest brings it to the next level. It’s almost like you’re cooking the dates in an Old Fashioned. Don’t worry — the bourbon will get boiled and it doesn’t leave a strong, overpowering flavour. That being said, you can most definitely sub water (or do half booze and half water) and these cookies will still be A+ delicious. I also can’t afford to put 3/4 cup of bourbon in all my desserts so I have definitely made these babies using water.

Picture of cookies in a tin

These Oatmeal Date Sandwich Cookies pair perfectly well with a cup of coffee or tea for a late morning or afternoon snack. As the days get gloomier and cooler, it’s important to make sure that you’re cozy! And what’s more cozy than the smell of cookies and wafts of cinnamon coming from the oven? 

picture of cookies

More vegan and gluten-free treats for the autumn

  • Apple Tart
  • Pumpkin Spice Muffins
  • Jumbo, Bakery-Style Cookies
5 from 4 votes
Oatmeal Date Sandwich Cookies
Prep Time
15 mins
Cook Time
28 mins
Cooling Time
1 hr
Total Time
1 hr 43 mins

Perfectly spiced oatmeal cookies are filled with a bourbon spiked date spread to make the ultimate vegan and gluten-free Oatmeal Date Sandwich Cookies.

Course: Dessert, Snack, Sweets
Keyword: Cookies, Dessert, Gluten Free, Vegan
Servings: 12 sandwich cookies
For the Oatmeal Cookies
  • 1 1/2 cups rolled oats (certified gf if required)
  • 1 cup + 2 tbsp Bob's Red Mill All Purpose Gluten-Free Flour
  • 1 tsp cinnamon
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1/2 cup vegan butter (I used vegan becel)
  • 1/2 cup brown sugar
  • 1 tbsp maple syrup
For the Date Filling
  • 2 cups chopped dates (not fresh), loosely packed* (about 325-350 grams)
  • 3/4 cup bourbon or whiskey (can sub water, or do half and half)
  • 1 tbsp fresh squeezed orange
  • zest of one small orange
  • 1/4 tsp salt
For the Oatmeal Cookies
  1. Preheat the oven to 350 degrees Farenheit and line a baking sheet with parchement.

  2. In a small bowl, combine the oats, flour, cinnamon, baking soda, and salt.

  3. In a large bowl, beat together the vegan butter, sugar, and maple syrup until for 2 minutes.

  4. Add the dry ingredients to the wet ingredients, and mix well. You will probably need to get your hands in there!

  5. Roll the cookie dough into 1 tbsp balls – you should get 24 cookies (and then 12 cookie sandwiches).

  6. Place on the parchment line cookie and flaten the balls with the palm of your hand. If any pieces crumble out a bit, gently squeeze them back in.

  7. Bake for 12-14 minutes. Let cool on the cookie sheet for a couple of minutes before moving to a cooling rack. Let the cookies cool completely before making into sandwiches.

Make the Date Filling
  1. Place the dates, bourbon or water, orange juice and zest, and salt into a small saucepan.

  2. Over medium high heat, bring to a boil.

  3. After it's come to a boil, turn the heat to low and simmer, uncovered, for about 12-15 minutes, stiring ocassionaly. It will start to thicken pretty fast (and then stop "simmering" due to lack of liquid). But keep cooking it, as you want it to be a thick enough to be sandwiched in between cookies without oozing out everywhere! It will, of course, firm up a bit when it is cool.

  4. When it is done, let cool compltely before using.

Assemble the Oatmeal Date Sandwich Cookies
  1. After everything has cooled, spread a generous amount of date filling on a cookie and then top with another cookie.

  2. Store in an airtight container and let the cookies sit for a few hours, or overnight. This time lets the flavour meld, while also alowing the filling to soften the cookies a bit.

  3. Enjoy! (you can totally eat them right away too, I do)

Recipe Notes

*When I say not fresh, I mean not the super fresh soft, buttery dates. You want to use (at least slightly) dried dates, or your filling will be too thin. I used the variety that comes in a block for baking.