Cinnamon It’s-It Ice Cream Sandwiches

Hi Bakers!

The crew was sitting around the backyard after dinner, as we do during these deliciously mild summer days and someone, perhaps one of my parents, mentioned It’s-Its. I don’t even know what the conversation was about, but the reference to the ice cream treat piqued my interest. My mind quickly went into “Ooo! How can I make that at home?” mode - typical. Like, wouldn’t those be so satisfying to bake yourself? And thus, that is how most things get done around here.

I made these cinnamon ice cream-filled oatmeal cookie sandwiches on a Task Saturday. With the conclusion of summer baseball behind us and a few weeks until our fall activities resume, we are trying not to waste any free weekends. That includes ticking things off the chore chart, because what better feeling is it to put in some work, build something with your own hands, and cross things off a list?

Of course I’m partially joking about making chores fun and, okay, my “chore” was baking cookies, but it got me thinking about where we spend our time. In the age of DoorDash, ChatGPT, and other promises to streamline, add convenience, and unburden us, what are we even doing with that extra time? Surely it’s not to gain another hour of TikTok or Love Island, right?

Instead, get out and make something. Whether that’s finally repairing and painting the posts outside like my husband did, or encouraging your pre-teen to wash and restore all his baseball hats with his uncle, or making ice cream sandwiches from scratch, I’m pretty sure you’ll end the day with satisfaction. AI still can’t unload a dishwasher, but don’t let it steal the little joys and accomplishments of completing a task actually worth your time. Just something to think about as you enjoy these cookie sandwiches…

What’s an It’s-It, you ask? It’s a legendary ice cream sandwich from 1920’s San Francisco. It all began when George Whitney scooped vanilla ice cream between two old-fashioned oatmeal cookies and dipped it in chocolate. The brand grew over the next several decades, expanding to multiple flavors and accessibility west of the Rockies (now shipping across the US).

For this recipe, I landed on cinnamon ice cream. I love cinnamon in my oatmeal cookies! And while I was making the custard base, I subbed maple syrup for part of the sugar. The ice cream itself tastes like French Toast.

The cookies are giant and chewy. Some might say a little too large for ice cream sandwiches, but I think that’s impossible. They are stuffed with rolled oats, plump raisins, and chocolate chips. Instead of dunking the whole thing in chocolate, I dipped an edge of the cookies before assembling.

• I intended for the cookies to remain soft and fresh. Ice cream sandwiches get so fussy once the cookies freeze and are difficult to eat.

• Instead, scoop and serve right away. The homemade ice cream will melt much faster than stabilized commercial ice cream.

• The ice cream and cookies can both be made in advance but just wait until putting them all together.

1 cup (240ml) milk
5 cinnamon sticks, broken into large pieces
2 cups (480ml) heavy cream, divided
½ cup (120ml) maple syrup
¼ cup (50g) granulated sugar
4 egg yolks
2 tsp vanilla bean paste or extract
Pinch salt

• Bring the milk to a slow simmer over medium heat. Remove from the heat and add the cinnamon sticks. Cover and let rest for about 1 hour.

• Strain the milk through a mesh sieve. Discard the cinnamon sticks.

• Warm the cinnamon milk along with 1 cup (240ml) heavy cream, maple syrup, and sugar over medium heat. Add the egg yolks to a large, heat-safe bowl.

• Once the milk mixture begins to steam and slightly simmer around the edges of the pan, remove from the heat. While whisking, slowly pour the milk mixture into the egg yolks. Keep whisking until combined.

• Pour the new egg mixture back into the saucepan and set over medium-low heat. Gently cook, while stirring, until the mixture thickens enough to coat the back of a spoon (170 to 175°F).

• Pour the custard through a mesh sieve into a clean bowl. Whisk in the remaining cream, vanilla, and salt to the custard.

• Chill the custard in the refrigerator until completely cool, at least 2 hours.

• Churn the ice cream custard according to the manufacturer’s directions. Freeze until ready to serve.

2 cups (250g) all-purpose flour
1 tsp baking soda
1 tsp ground cinnamon
½ tsp baking powder
½ tsp salt
1 cup (227g) unsalted butter, softened
¾ cup (150g) granulated sugar
¾ cup (150g) brown sugar
2 eggs
2 cups rolled oats (175g)
1 cup (150g) raisins
1 cup (170g) chocolate chips

4 ounces (113g) dark chocolate, chopped
2 tsp coconut oil

• Preheat the oven to 350°F. Line cookie sheet pans with parchment paper and set aside.

• In a medium bowl, combine the flour, baking soda, cinnamon, baking powder and salt. Set aside.

• Using an electric mixer, beat together the butter, granulated sugar, and brown sugar for 2 to 3 minutes. Add the eggs and mix until blended.

• Add the flour mixture and mix just until combined. Add the oats, raisins, and chocolate chips and mix until combined.

• Using a large cookie scoop, form the dough into large balls (I used two scoops per cookie). Place 5 to 6 cookies on each sheet pan and gently flatten.

• Bake for 12 to 14 minutes, or until slightly golden brown around the edges and nearly set on top (it’s okay if they are still soft in the middle).

• Cool on the baking sheet on a wire rack for 10 minutes before transferring.

• Once the cookies are cool, melt together the chopped chocolate and coconut oil over a double-boiler.

• Pour the melted chocolate into a small bowl. Divide the cookies in half. Dip a portion of half of the cookies in the melted chocolate and set on a clean piece of parchment to dry. You can speed up the drying by placing them in the refrigerator.

• When ready to serve, scoop the ice cream onto the bottom halves and sandwich together with the chocolate-dipped cookies. Eat immediately.

• This recipe makes 6 to 7 large ice cream sandwiches. They are best served right after assembling so that the cookies remain soft.

• Be aware that the homemade ice cream melts very quickly, so scoop only when ready to serve.