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We Recreated an It's-It Ice Cream Sandwich at Home — With an Oakland Twist.

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A triptych image with a close up of rocky road ice cream on the left, a tray of oatmeal cookies on the right, and a young bald Filipino man with glasses standing over a chocolate ice cream sandwich in the middle
Josh Decolongon recreates the famous San Francisco It’s-It using homemade rocky road ice cream, a flavor that was invented in Oakland. (Josh Decolongon)

 

A list of things that are very San Francisco are never complete without the It’s-It ice cream sandwich. Invented by Playland-at-the-Beach amusement park owner George Whitney in 1928, an It’s-It is a scoop of ice cream sandwiched by two oatmeal cookies and then dipped into chocolate. In my opinion, the key components are the oatmeal cookies (where there are raisins: I’ve checked!), which provide a soft snap that somehow lightens the load of a regular cookie while also giving me the comfort and warmth of my grandma’s oatmeal cookies — perhaps a reminder that San Francisco is never as warm as an American summer promises. But I’m okay with that.

Any recreation experiment begs the question: why make your own? We’re spoiled with choice and availability in the Bay, so I’d absolutely be able to run blindfolded in any direction for half an hour before bumping into the storied ice cream treat. But, aside from the fact that I like to give myself a challenge, I simply like to create new flavor combinations. It’s-Its come in vanilla, chocolate, mint, and cappuccino, along with seasonal strawberry and pumpkin flavors, but I went off-script to make a version that was even more of an ode to the Bay Area with rocky road ice cream, a flavor that was actually invented in Oakland. In the 1920s, ice cream entrepreneur William Dreyer wanted to raise people’s spirits during the Great Depression and decided the best way to do so was with a combination of chocolate ice cream, nuts, and marshmallows.

First of all, I’m not going to stop you from doing your own thing. You can find your own oatmeal cookie recipe (or buy them), your own ice cream recipe (or buy it), and your own chocolate shell recipe (or buy it) and call it a day, but this is what I did. Many recipes veer fancy in order to get as close to an It’s-It as possible, but again: why recreate it when you can re-interpret it? If the Bay Area has taught me anything, it’s that there’s room for all flavors to exist here.

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You can go up to a cup for each ingredient for the rocky road ice cream, but sometimes the dual textures of the hard almonds and soft marshmallows throws people off. I am not one of those people, obviously.

A triptych image with a close up of rocky road ice cream on the left, a homemade It's-It's ice cream sandwiches on the right, and a a cross-section of both the homemade It's-It and real It's-It in the middle
Recreating the storied It’s-It ice cream sandwich from scratch requires several stages: making the ice cream, making the oatmeal cookies, and dipping them in chocolate. (Josh Decolongon)

Ingredients for the oatmeal cookies:

  • ¾ cup all-purpose flour
  • ½ teaspoon ground cinnamon (preferably Ceylon)
  • ½ teaspoon baking soda
  • ¼ teaspoon baking powder
  • ¼ teaspoon salt
  • ½ cup unsalted butter
  • ¾ cup brown sugar
  • ¼ cup white sugar
  • 1 egg
  • ½ tsp vanilla extract
  • 1 ½ cups quick cook oats (e.g. Quaker Oats Quick 1-Minute Oats)
  • ¼ cup chopped raisins
  1. Preheat oven to 350°F.
  2. In a medium bowl, combine the flour, ground cinnamon, baking soda, baking powder, and salt. Combine well – it always takes longer than you think it does!
  3. In a large bowl, cream together the butter, brown sugar, and white sugar for around 5 minutes. Along with the rising agents, creaming this mixture creates a fluffier and softer cookie — just make sure your butter isn’t too warm, because it’ll be harder to create these micro-pockets of air. Add the egg and vanilla, and continue to beat together until combined. With a spatula, gradually add the flour mixture to the creamed mixture.
  4. Combine the oats and raisins, the latter which, again, are definitely there in the original.
  5. Shape into balls around an inch or so in diameter — you should have roughly enough dough for 22 cookies. Bake for around 12 minutes, and then cool them on wire racks.
  6. Optionally, you can flatten the cookies slightly with a flat kitchen utensil (like a flat spatula), but that’s totally up to you.

Ingredients for the rocky road ice cream:

  • 1 pint (16oz / ~480mL) heavy cream, cold
  • 1 can (14oz / ~400g) sweetened condensed Milk
  • ½ cup cocoa powder
  • ½ cup (or up to 1 cup) crushed almonds 
  • ½ cup (or up to 1 cup) mini marshmallows (or cut up large marshmallows)
  1. Whip heavy cream until there are stiff peaks.
  2. Add sweetened condensed milk and cocoa powder. Beat on low speed until the mixture is homogeneous.
  3. Add the crushed almonds (I like putting them in a ziplock bag and mashing them with the handle of my rolling pin) and mini marshmallows to the mixture. Gentle combine with spatula.
  4. Add the mixture to a container and top with more crushed almonds and mini marshmallows, if you’d like.
  5. Cover and freeze overnight.
  6. Lick spatula.

Ingredients for the chocolate shell:

  • 14 oz bittersweet chocolate (but you can vary the ratio with semisweet chocolate, which I did)
  • ¼ cup coconut oil
  1. Heat up water in a saucepan or pot.
  2. Place both the chocolate and oil into a metal bowl that can fit on top of a saucepan or pot without being able to fall in completely. The water should have contact with most of the bowl.
  3. Stir the mixture occasionally until it is homogeneous.
  4. Let the mixture cool for 20 minutes or so. We want it to be cool enough to coat our homemade It’s-Its without melting the ice cream, but warm enough so that it can cover them easily.

To assemble:

  1. Now that you have all your ingredients, remove the ice cream from the fridge and let it warm up for 10 minutes or so to soften it up slightly.
  2. Scoop ice cream and press onto the flat side of the oatmeal cookie until your heart’s desire. You want around an inch of thickness of ice cream. Sandwich the ice cream with another cookie.
  3. Using an ice cream spatula, or a spoon, take more ice cream and fill the sides of the ice cream sandwich, smoothing out bumps and filling the empty spaces as you rotate it. When you’re happy with it, immediately transfer them to the freezer for around an hour.
  4. Using tongs, dip and flip your ice cream sandwich into the melted chocolate shell mixture and let it briefly rest on a wire rack. You can scrape excess chocolate off if you’d like a thinner shell.
  5. When the chocolate has hardened and takes on a more matte texture, transfer immediately to the freezer.

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Josh Decolongon is a certified sommelier and holds the WSET Level 4 Diploma. He is the host and producer of “No Crumbs,” a new digital video series from KQED. Find it on Instagram @KQEDFood. Follow Josh on Instagram at @sommeligay.

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