Date Filled Oatmeal Cookies

Soft, chewy and filled with a sweetened date filling, this handed down vintage recipe for Date Filled Oatmeal Cookies is easy to make and the cookies are delicious with a cup of coffee or tea.

If you love cookie recipes, add my Monster Cookies, Laura Bush’s Cowboy Cookies and Lofthouse Sugar Cookies to the baking list too!

this recipe!

What are trilby’s or trilbies cookies?

Trilby’s or trilbies is a one hundred year old cookie name for making an oatmeal filled cookie or oatmeal turnover cookie filled with dates.

Were these trilby cookies so named after the Trilby hat? Nobody seems to know but it is a fun history attached to these delicious date filled oatmeal sandwich cookies.

If you’ve never experienced Date-Filled Oatmeal Cookies, you’ve gotta try them. The sweetened dates are a perfect pairing, sandwiched between two delicious soft oatmeal cookies.

This oatmeal date turnover cookies recipe takes a bit more work with the date filling, but the filling is quick and easy to make with basic steps and takes only about five minutes.

My husband kept buying these oatmeal filled with dates cookies at the grocery store, so I asked my mom for her recipe of my grandma’s and I made them for him. He has never bought them at the store again!!

Ingredients and notes for old fashioned date filled oatmeal cookies

• Butter and eggs should be at room temperature
• I use the quick oats in this recipe
• Dates can readily be found in the grocery stores. My favourite brand is the Jaffa dates

Substitutions for old fashioned date cookies recipe

I have made these date filled cookies many times and my mom before me and they always come out perfect.

This is one of the tried and true recipes with dates and oats that I do not recommend substituting any ingredients, besides what oats you want to use in this date recipe.

If you’re going to use old-fashioned oats, give them a few quick pulses in the food processor first.

Why you’ll love this date oatmeal cookie recipe

• Easy to make tried-and-true, passed down for generations old-fashioned date filled cookies with oatmeal
• Classic nostalgic date filled oatmeal cookie for your holiday baking platter
• Comfort food cookie that delivers a lot of flavor

Step by step instructions for how to make easy date filled oatmeal cookies

You can find a full printable recipe card by scrolling to the bottom of this post.

This is a basic cookie recipe.

STEP ONE – You start by combining the butter and both sugars.

I like to use a stand mixer with the paddle attachment or you can also use a hand mixer. In a pinch, you can mix these cookies by hand. The key to mixing by hand is to ensure that the mixture is light and fluffy which will require a good arm workout!

STEP TWO – Add in the eggs and vanilla and mix until well-combined.

STEP THREE – In a separate bowl, combine the all-purpose flour, baking soda, baking powder, cinnamon and salt.

STEP FOUR – Add the dry ingredients to the butter mixture and stir just until combined.

STEP FIVE – Next, add in the rolled oats and stir until combined. At this point, it might be easier to mix in with a wooden spoon, or with clean hands because the mixture will be quite thick.

STEP SIX – Scoop up a heaping tablespoon of cookie dough and roll it into a ball, then flatten to about 2 and 1/2 inches across. The cookies will spread a little, so leave a few inches between them on an ungreased or parchment paper-lined baking sheet.

STEP SEVEN – Bake in 350°F oven for 10 to 12 minutes. The baked oatmeal cookies will still be slightly soft in the middle.

STEP EIGHT – Allow the cookies to cool before spreading with the date filling.

Making the date filling for oatmeal cookies:

STEP NINE – Combine chopped dates, water and sugar in a saucepan. Bring to a boil. The mixture is cooked when it has thickened. This happens quickly, so keep a close eye on the mixture and continue to stir as it comes to a boil.

STEP TEN – Spread the date filling onto the flat side of the cookie, then sandwich with another cookie, flat side down. Think of it as making a date filled sandwich cookie.

Variations for oatmeal date filled cookies

You can sprinkle a little turbinado sugar on top of these date sweetened cookies. I find these delicious soft cookies plenty sweet enough all ready but I know add the sugar to the tops is liked by many.

Chopped walnuts or pecans can be added to the date filling or oatmeal cookie dough to make date-walnut oatmeal cookies.

Sandra’s top tips for making the best date filled oatmeal cookies

• Room temperature butter and eggs is a must for baking these oatmeal cookies with dates
• Measure ingredients properly and use the scoop and level method for measuring the flour, as too much flour can dry out the cookie
• Make sure your mixture is light and fluffy. That is why I like to use the stand mixer
• Know your oven adjust temperature accordingly, an oven that does not reach the correct temperature can cause the cookies to spread too much
• Cookies must cool before adding date filling
• You can add a thicker amount of date filling but I find that to be too sweet and overpowering but find what thickness works for you

How to keep my oatmeal cookies soft?

It is important to use an airtight container to store them and throw in a piece of white bread in the container or zippered bag to help keep them moist and soft.

The cookies will absorb the moisture from the bread helping to keep them soft.

Storage and freezing instructions for oatmeal date cookies

Storing date oatmeal cookies

Store in an airtight container for up to 5 days or for 7 days in the fridge. Parchment paper between the layers is a good idea so the old fashioned date filled cookies do not sick together.

Can you freeze oatmeal date filled cookies?

Yes you can! Freeze with using parchment paper between any cookie layers in a freezer-safe container for 2 to 3 months.

Thaw in the fridge or at room temperature before serving.