Chocolate-Cherry Roll Cookies

The Chocolate Cherry Roll. It has been the delectable must-have of every holiday and every birthday in our extended family for years!

Light and fluffy cherry-coconut filling rolled up in a soft, moist chocolate cake, drizzled with smooth chocolate glaze, and garnished with maraschino cherries and the occasional dusting of powdered sugar and/or coconut flakes.

Mmmm... my mouth is watering just writing about it!

The absolute most sought-after heirloom recipe in the pool of our family's greatest traditions.

But the joy and beauty of passed-down family traditions is watching how they are tweaked and developed through the years, marking the different tastes and styles of each unique family under the bigger family umbrella.

Something our family wanted to do with this recipe is put our own mark on the traditional roll.

Could we develop a COOKIE that is just as delicious and passing-on-able as the original roll?

This, is the moment of truth! Can we make a mark on history, too?

Well, as long as we do it TOGETHER, it will be a beautiful adventure...That's what FAMILY is all about...

*Note: I used the basic recipe from Bunsen Burner Bakery here to get a basis for my pinwheel cookies. Then I tweaked it to make it my own.*

Supplies

Chocolate-Cherry Pinwheel Cookies:

3 cups all-purpose flour

1/2 teaspoon baking powder

1/2 teaspoon salt

1 cup butter, room temperature

1 1/3 cup sugar

2 large eggs

2 teaspoons vanilla

1/4 cup semi-sweet chocolate chips

1/4 cup maraschino cherries, finely chopped

OPTIONAL: 10 (or more) drops of red food coloring

Cherry Coconut Filling:

1 cup heavy whipping cream

3 Tablespoons powdered (confectioner) sugar

1/3 cup maraschino cherries, well drained and chopped

1/2 cup sweetened coconut flakes (you can opt out of the coconut if you don't like it)

Baking Supplies

Plastic Wrap

Parchment Paper

2 large mixing bowls

1 small microwaveable bowl (or a double boiler or 2 pots) for melting chocolate

Whisk, spoon, and/or fork

Electric hand mixer (or standing mixer) with adjustable speeds

Bench scraper, spatula, or use the back of a knife

Knife (for cutting the dough)

Step 1: Making Memories

It is important for me to preface this Instructable with a little note of encouragement.

Part of the fun and beauty of family traditions is spending time being TOGETHER and making memories.

We don't have a lot of time on planet earth, and our time can be taken away in a moment's notice, so it's important to make every moment--every breath in our lungs--count!

I enjoyed making these cookies with my kids! It was fun making messes, figuring out how to correct mistakes, and taking chances on a crazy idea together. It will forever be memorable not because the food tasted great, or because everything went along smoothly with no imperfections, but because the struggles make the successes even greater, and the imperfections make our family even better! It's because LOVE is irreplaceable and that means more to us than a "perfectness" that is truly unattainable.

So, I encourage you (if you can or want to) to make this a fun getting-together moment with someone you love or some of your favorite friends! The memories (whether you succeed or fail) are ALWAYS worth it! :D

Step 2: Sift

I chose to do a pinwheel design for the outside cookies to pay homage to the original roll. The chocolate and cherry swirled dough of the pinwheel cookies gives the finished sandwich cookie the look and taste of our beloved heirloom recipe!

In a medium to large bowl, sift in the flour, baking powder, and salt.

Step 3: Beat

In the second bowl, use an electric mixer on medium speed to beat the butter until it is light and fluffy.

About 3 minutes.

Step 4: Add Sugar

Add in the sugar and beat an additional 2 minutes.

Step 5: Add the Eggs

Add in the eggs one at a time. Beat after each addition.

Step 6: Add Vanilla & Flour

Add in vanilla and the flour mixture from the first bowl, then using a whisk, fork, or the electric mixer on low speed, mix it all together until just combined.

Step 7: Divide the Dough

Divide the dough in half. Set aside one half in plastic wrap and leave the other half in the mixing bowl.

We put some plastic wrap over the dough in the mixing bowl to keep it from drying out while we completed the next step.

Step 8: Melt the Chocolate

Place the chocolate chips in a microwaveable bowl (or you can use the double boiler method).

On very low power (I alternated between 30-50% power levels), heat the chocolate chips for 30 seconds. Then take out and stir. Then heat for another 30 seconds, and take out and stir.

Continue this process until the chocolate is beautifully smooth.

DO NOT OVERHEAT THE CHOCOLATE. Take your time to get it right.

Step 9: Make Chocolate Dough

Mix the melted chocolate into the dough until just combined.

And don't forget to lick out the melted chocolate bowl afterwards! Very important!!

Step 10: Refrigerate

Form the chocolate dough into roughly a 4" x 4" square, wrap it in plastic wrap, and put it in the refrigerator.

Step 11: Clean & Dry the Bowl

Clean and dry the bowl (at least one of the two of them) to get it ready for the cherry dough.

Step 12: Finely Chop Cherries

Finely chop the cherries.

Be careful going out in public for a few hours...someone might think you were part of a murder scene when they see your hands!

Step 13: Make Cherry Dough

Add the second half of the dough to the clean bowl.

Add in the chopped cherries and an optional 10 drops (give or take depending on how red you want the dough to be) of red food coloring. Then mix until just combined.

NOTE: Be careful adding in juice (for flavor) from the maraschino cherry jar. I originally tried this and it watered down the dough to a too-sticky consistency that was unusable. :( You can attempt it if you want, and play around with it until it forms the correct consistency. But just a fair warning of what to expect adding it as-is to this recipe.

Step 14: Refrigerate

Form the cherry dough into roughly a 4" x 4" square, wrap it in plastic wrap, and put it in the refrigerator.

Put on a timer for at least 30 minutes. You can leave the dough in the refrigerator for up to 3 days if needed.

You want to keep the dough in the refrigerator until it firms up and is easier to use.

Step 15: Cut Dough

Remove the chocolate dough from the refrigerator.

Lay out a piece of parchment paper onto your work surface and turn the dough out onto it.

Cut the dough into four even strips, cutting lengthwise.

Leave one strip of dough on the parchment paper, and return the other strips to the fridge to keep them cold, wrapped up in separate pieces of plastic wrap.

NOTE: It isn't necessarily required to return the remaining strips to the fridge, but I found it easiest to work with cold dough, and I wasn't taking any chances of leaving it out.

Step 16: Roll the Chocolate Dough Strip

NOTE: You need to work quickly for these next few steps. Any dough left out of the refrigerator for too long will start to get too soft (and therefore too sticky) and you will have to return it to the refrigerator to wait for it to firm up again before continuing. Extra hands make this process that much easier! :)

I highly recommend working with only ONE chocolate dough strip and ONE cherry dough strip at a time.

Put another piece of parchment paper over this strip of chocolate dough.

Roll out the dough to only about 6-7 inches long in a mostly rectangular shape.

Step 17: Cut & Roll the Cherry Dough Strip

NOTE: You will be using A LOT of parchment paper and plastic wrap sheets for these steps. It is important to use new, fresh sheets every time there's a change.

Put a different sheet of parchment paper down on the work surface.

Turn out the cherry dough on to it. Cut the dough into 4 equal strips, cutting lengthwise. Save the extra strips in separately wrapped plastic sheets in the refrigerator.

Roll out the cherry dough strip that remains on the parchment paper, like you did the chocolate dough strip.

I found it was easiest (because my cherry dough was a little softer than the chocolate dough) to use a plastic sheet over the cherry dough for rolling it (instead of parchment paper). The parchment paper on top seemed to make a sticky mess with the dough.

ALTERNATIVELY: You can turn out the cherry dough strip directly on top of the flattened chocolate dough before rolling it. This worked OK.

Step 18: Combine Dough

Remove the parchment paper top of the chocolate dough and the plastic wrap top of the cherry dough, and carefully but quickly flip the cherry dough on top of the chocolate dough.

It may squirm and miss the mark a bit, but IT'S ALL GOOD! That's part of the fun!

Lightly roll or press with your hands over the parchment paper covered cherry dough (the original bottom sheet under the dough) to combine the cherry and chocolate dough.

Step 19: Cut Out a Rectangle

Trim the edges of the combined dough into a rectangle.

(Sorry! I had started to do the next step before taking a picture of the trimmed rectangle.)

Step 20: Roll Up the Dough

Using a bench scraper, or the back of the knife, start rolling up the dough. First from the middle, then working toward each end until you have a line of rolled over dough.

Use your hand (and/or the metal scraper if the dough is slightly sticky) to continue rolling the dough up into a log.

NOTE: If you want smaller cookies but more of them, roll it from the long side up (like I did). If you want bigger cookies with less of them, roll it from the short side up.

Step 21: Wrap and Refrigerate

Wrap the log in plastic wrap and refrigerate.

REPEAT FOR ALL FOUR LOGS.

Refrigerate all logs for 1 hour.

Step 22: Keep 'Em Round & Freeze

After 1 hour, take out each log and roll them gently on the countertop or a work surface to keep them round (instead of going flat on the bottom).

Transfer the logs to the freezer. Freeze for 2 hours, or up to 3 months.

*IMPORTANT NOTE: Keep the logs frozen until or unless you are ready to slice and bake them. You can add the plastic-wrapped logs to sealable freezer bags (to keep them from getting a freezer-burnt taste) should you wish to use them at a much later date.

Step 23: Slice & Bake

Preheat the oven to 350°F.

Line a baking sheet with parchment paper.

Take a log out of the freezer (or all 4 logs depending on how many cookies you want to make at once).

Using a sharp knife, cut 1/4" thick slices and place them 1" to 1 1/2" apart on the baking sheet.

Bake for 7-9 minutes for small cookies, or 9-11 minutes for larger cookies. Depending on your oven or size of your logs, it might take more or less time. Just watch them to make sure they don't burn.

NOTE: My logs made roughly 32 cookies each. But yours may make more or less depending on how you rolled up your dough, and the width and length of the logs you created.

Step 24: Make the Cherry Coconut Filling

While the cookies are baking, use this time to make the absolutely divine cherry coconut filling! The recipe for this filling is directly from the original chocolate cherry roll. Mmmmm!!!! Bringing the two together!

In a medium bowl, beat cream until slightly thickened.

Add sugar and beat until stiff.

Fold in cherries and coconut.

OPTIONAL: If you so desire, you can add red (or whatever color) food coloring to the filling.

Keep in the refrigerator with plastic wrap over it until ready to use.

Don't forget to clean up the beaters! ;)

Step 25: Cool the Cookies

Remove the cookies from the oven and cool on a wire rack.

If you don't have a wire rack, remove the parchment paper from the baking sheet and cool them on that.

Cool completely before proceeding. The wait may prove exceedingly difficult...

Step 26: Assemble the Finished Cookie

Melt a little bowl of chocolate chips the way you did previously.

On a pinwheel cookie, add a scoop of the filling.

Then dunk the top of the second pinwheel cookie in melted chocolate.

Press the chocolate-covered pinwheel cookie (chocolate side up) on top of the filling-covered pinwheel cookie to complete the assembled cookie.

ALTERNATIVE: If you want to show off the swirls on the pinwheel cookies, assemble as follows...

• On the inner sides of the top and bottom pinwheel cookies, dip them in the melted chocolate.
• Add filling on top of the bottom chocolate-covered pinwheel cookie.
• Add the top pinwheel cookie with the chocolate facing into the filling. (Both chocolate sides should be touching the filling.)
• Now the pinwheel on top will show. Garnish as desired, or add no garnish.

Step 27: Garnish

Add a beautiful garnish to the tops of the finished cookies.

Garnish options include, but are not limited to:

• Chocolate drizzle
• Powdered sugar
• Maraschino cherry chunks
• Coconut flakes

Step 28: It's WORTH IT!

It's finally time to devour (I mean, enjoy) these oh-so-yummy cookies! Mmmmm....

The chocolate-cherry cookies are soft and chewy...Yummmm....

The filling is light and fluffy and packed with delicious cherry-coconut flavor...Yes, please!!

The decadent chocolate coating on the assembled cookie amplifies the entire cookie experience! Gotta...have...just...one...more...

These are so addicting that my kids kept eating them up before I could plate them for the final pictures!

So, what's my kids' verdict? Do these measure up to the original roll?

Drum roll please (MOM, STOP READING HERE)....

They thought they were *better* than the original roll!

Whoa! Didn't see that coming!! A feat for sure!!

So, what unique family traditions will you make this year?

Remember, you don't need a special holiday to make special memories together...throw on an apron and let the fun begin! There's always adventures to be had in a kitchen (the heart of the home)!