Chocolate Cherry Squares Cookies look like they took you a long time to make them, but they are SO easy. A simple shortbread bar cookie, topped with chocolate and cherries. Yum!

Chocolate Cherry Squares Cookies are so pretty on the plate and people love them.
CHOCOLATE CHERRY SQUARES cookies are divine.
Today I’m telling you about Chocolate Cherry Squares, a beautiful bar cookie I have been making annually since the 1980s. It’s one of my all-time favorite cookies. With the holidays just around the corner, I am again posting some of my favorite holiday recipes.
Let me tell you a “funny story” about these cookies. One year I mailed my daughter Erin a box of these cookies along with several other chocolate cookies and candies. Her roommate put the box under the tree without opening the outer box, never thinking it might contain food.
Their two dogs got into the package in the middle of the night, eating most of the goodies. (Did you know dogs can die from eating chocolate?) It took two emergency trips to the vet and cost her about $1,000 to save their lives, and she didn’t get one cookie from the batch!

A pan of Chocolate Cherry Squares before plating.
Even though Erin no longer has any pets, since then, I send any edible goodies to Erin’s office.

Chocolate Cherry Squares, ready for guests.
For Gluten Free
Since I have found I can no longer tolerate gluten, I’ve been making these cookies using gluten-free flour. The bottom layer of this cookie is a simple shortbread bar cookie. You can substitute my Gluten Free Shortbread Cookies for the bar cookie in this recipe. My favorite GF flour is Bob’s Red Mill 1-to-1 Baking Flour.
What You Need
For this recipe, you need measuring cups and spoons, a jelly roll pan, a small knife, a double boiler or a microwaveable bowl, and a butter knife. But what you really want is a fancy espresso machine, right?
Chocolate Cherry Squares Cookies Recipe

Chocolate Cherry Squares
These are easy bar cookies that look very hard to make. At the holidays, they are beautiful served with other Christmas cookies.
Ingredients
Cookie
- 1 cup sifted flour
- 1/4 teaspoon salt
- 1/3 cup brown sugar
- 1/2 cup butter (or margarine)
Topping
- 1 cup chocolate chips
- 1 10-ounce jar of maraschino cherries (drained, each cherry cut in half)
- crushed nuts (optional)
Instructions
- Combine first three cookie ingredients.
- Cut in butter.
- Shape into a ball.
- Press into an 8" x 8" pan.
- Bake at 350F degrees for 20 minutes.
- The cookies will be just slightly brown when they are done.
Cut into 2" squares while still warm (very important).
- Melt chocolate chips.
- Top each cookie square with a dab of melted chocolate.
Put 1/2 a cherry on top of each dab of chocolate.
- With a teaspoon, dab more chocolate over the cherry.
- Sprinkle with crushed nuts.
- Set aside until chocolate is firm.
https://recipeideashop.com/chocolate-cherry-squares/
Recipe Notes
If you double the recipe, use a 9" x 13" pan. For a cookie sheet, multiply the recipe by four.
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Recipe Nutrition Information
The information shown is an estimate provided by an online nutrition calculator. It should not be considered a substitute for a professional nutritionist’s advice.
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