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Homemade IT’S-IT Ice Cream Sandwiches

Before summer ends, it’s time for one final homemade dessert to send the season off with a cool and creamy salute.

We’ve already tackled strawberry shortcake ice cream bars and Drumstick cones, so I think we’re all up for a new challenge: homemade IT’S-IT ice cream sandwiches.

If you haven’t heard of this iconic San Francisco ice cream treat, let me enlighten you.

stack of mint and chocolate its-it ice cream sandwiches
Photo: Casey Barber

IT’S-IT ice cream sandwiches have been a cult favorite in the Bay Area since 1928, originally sold at the amusement park Playland-at-the-Beach and growing in popularity over the past century.

What’s an IT’S-IT ice cream sandwich?

There are a few things that set IT’S-IT ice cream sandwiches apart from a Chipwich or other cookie-based ice cream sandwich.

The most obvious difference is that the entire sandwich is dipped in a thin layer of chocolate shell, Klondike bar-style.

The other difference—and the most crucial element, in my professional opinion—is that IT’S-IT sandwiches are made with oatmeal raisin cookies.

stack of strawberry, chocolate and mint its-it ice cream sandwiches
Photo: Casey Barber

Not chocolate chip cookies. Not cakey chocolate cookies. Oatmeal raisin cookies!

Yes, there are raisins in there. Unlike other people who can’t be bothered to read ingredient lists, I can assure you that it’s not an authentic IT’S-IT without raisins.

As an avid raisin hater, I can also assure you they are too small to be detectable here, but add an important level of moisture to the cookie. Let me explain.

The original It’s-It cookie recipe, according to the ingredients on the package, is simple. It only includes:

  • flour
  • brown sugar
  • palm oil
  • oats
  • raisins
  • baking soda
  • baking powder
  • salt
  • cinnamon

Based on this, it was easy for me to reverse engineer a homemade oatmeal raisin cookie.

The Secret to Perfect Oatmeal Raisin Cookies

I stuck to the package ingredient list as much as possible when making my IT’S-IT cookies.

I simply substituted shortening for palm oil and added a little extra liquid to make the dough a bit more pliable.

It's-It ice cream sandwiches both whole and sliced in half
Photo: Casey Barber

The real key to making these cookies as close in taste and texture to the authentic IT’S-IT cookies is to use a food processor.

The raisins and the oats should not be chunky here—the cookies should be thin and soft, but not cakey and molasses-y like a Little Debbie.

If you do want the recipe for a Little Debbie-style oatmeal cream pie, by the way, you can find that in my cookbook Classic Snacks Made from Scratch.

So by grinding the raisins and oats with the flour and other dry ingredients, I was able to achieve the ideal textural balance.

oatmeal cookies on a baking sheet
Photo: Casey Barber

And by incorporating the raisins this way, the cookie gets just about enough moisture to bind the dough together without other typical ingredients like butter or eggs.

Keeping the cookie ingredients simple really is best here.

Shaping the dough into discs on the baking sheet and then (gently) smashing them with a spatula immediately after they come out of the oven will give you the flat shape that’s ideal for these ice cream sandwiches.

Assembling the IT’S-IT

And these wouldn’t be ice cream sandwiches without the ice cream! IT’S-ITs have a lot of choices when it comes to ice cream flavors.

The company offers traditional vanilla and chocolate, but also branches out with mint, strawberry, cappuccino, and sometimes pumpkin and green tea.

So it’s up to you if you want to go classic or creative with the flavor of ice cream you put between your oatmeal raisin cookies.

stack of mint and chocolate its-it ice cream sandwiches
Photo: Casey Barber

My personal favorite is a mint IT’S-IT, but I have a soft spot for strawberry too.

To make the ice cream discs, slightly soften the ice cream enough to make it spreadable, then freeze into a slab.

With a 3-inch cookie cutter, you can stamp out rounds of ice cream, then assemble the cookie sandwich and freeze again until firm.

After that, all you need to do is dip the ice cream sandwiches in luscious two-ingredient chocolate shell.

The recipe below makes about 16 homemade IT’S-IT ice cream sandwiches, which is enough to stock your freezer for a few months.

stack of mint and chocolate its-it ice cream sandwiches

And here’s my pro tip: I like to cut each IT’S-IT in half after the chocolate shell has hardened.

That way, I can mix and match my ice cream flavors and double my fun.

Mint and chocolate? Vanilla and strawberry? It’s whatever IT’S-IT combination you want it to be this way.

It's-It ice cream sandwiches both whole and sliced in half

Homemade It's-It Ice Cream Sandwiches

Yield: 16 sandwiches
Prep Time: 1 hour
Cook Time: 45 minutes
Additional Time: 6 hours
Total Time: 7 hours 45 minutes

Homemade IT'S-IT ice cream sandwiches pay homage to the classic San Francisco treat with oatmeal cookies, ice cream and chocolate shell.

Ingredients

Cookies

  • 2 cups (160 grams) rolled oats
  • 1 cup (160 grams) raisins
  • 2 cups (240 grams) all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon kosher salt
  • 1/2 teaspoon cinnamon
  • 1 1/4 cups (263 grams) dark brown sugar
  • 1 cup shortening (regular or vegan)
  • 2 tablespoons milk (regular or non-dairy)

Ice Cream Sandwiches

  • 3 pints or 1 (1.5-quart) tub of ice cream, any flavors
  • 3 cups (18 ounces; 504 grams) semisweet chocolate chips
  • 5 tablespoons (140 grams) refined coconut oil

Instructions

Make the cookies:

  1. Preheat the oven to 350 degrees F and line two large baking sheets with parchment paper.
  2. Add the oats, raisins, flour, baking soda, baking powder, salt, and cinnamon to a food processor.
  3. Process for 10-15 seconds, until the raisins are chopped into small pieces—about the size of a whole oat flake.
  4. Set aside.
  5. In the bowl of a stand mixer fitted with the paddle attachment, beat the sugar and shortening together for 2 minutes on medium speed until light and fluffy.
  6. Scrape down the sides of the bowl.
  7. Stir in the dry ingredients on low speed in 1/4-cup increments until incorporated.
  8. Drizzle in the milk until incorporated. The dough will be soft and just a little crumbly.
  9. Scoop the dough onto the prepared baking sheets in heaping tablespoons.
  10. Shape each tablespoon mound with your hands into a slightly flattened disc on the baking sheet.
  11. Bake for 15-18 minutes, until the cookies are cooked through but not browning.
  12. Remove from the oven.
  13. Immediately press each cookie with a metal spatula to flatten it.
  14. Let the cookies rest on the baking sheet for 5 minutes, then transfer to a wire cooling rack and let cool completely.
  15. Repeat with the remaining dough. You should have about 32 cookies total.

Make the ice cream discs and assemble the sandwiches:

  1. If you're making different flavors of ice cream sandwiches, prepare each pint separately according to these instructions.
  2. Line a rimmed baking sheet with a silicone mat or parchment paper.
  3. Scoop the ice cream out of its cardboard container into a large mixing bowl.
  4. Gently smash and stir the ice cream with a silicone spatula just until it's soft enough to spread.
  5. With the spatula, spread the ice cream onto the prepared baking sheet into a rectangle approximately 1 inch thick.
  6. Place in the freezer and let freeze for 2-3 hours, until very firm.
  7. Remove from the freezer and use a 3-inch round cookie cutter to stamp out discs of ice cream. You should get about 6 discs from each pint or 18 total from a 1.5-quart container.
  8. Return the entire baking sheet to the freezer for about 30 minutes, just long enough to firm it up again.
  9. While the ice cream freezes, line half the cookies up on a cutting board or clean work surface to create an ice cream sandwich assembly line.
  10. Remove the baking sheet from the freezer and use an offset spatula to lift and transfer the ice cream discs to each cookie. You may need to use the cookie cutter again to separate the edges.
  11. Top each ice cream disc with a second cookie and place on a clean rimmed baking sheet.
  12. Transfer the ice cream sandwiches to the freezer and let them harden for at least 2 hours. It's the cook's reward to quickly eat the remaining pieces of ice cream too.

Finally, it's time for the chocolate dip:

  1. Place the chocolate chips and coconut oil in the top of a double boiler or in a heatproof bowl that will fit snugly over a small pot of water. Set aside.
  2. Add water to the bottom of a double boiler or to a small pot that can be snugly covered by the heatproof bowl and bring to a bare simmer over medium-low heat.
  3. Place the bowl of chocolate on top and stir constantly until the chocolate is mostly melted.
  4. Remove the bowl from the heat and stir to melt the last little bits of chocolate.
  5. Line a large baking sheet with waxed paper.
  6. One at a time, dip the ice cream sandwiches in the melted chocolate. Use a small spatula to help scrape excess chocolate off the cookies so that the layer of chocolate isn't too thick.
  7. Place on the waxed paper and repeat.
  8. After dipping about 8 sandwiches, transfer the baking sheet to the freezer and let the ice cream sandwiches chill.
  9. Repeat with a fresh baking sheet and the remaining ice cream sandwiches.
  10. Ice cream sandwiches will keep for about 3 months in a sealed freezer-safe container.
Nutrition Information:
Yield: 16 Serving Size: 1
Amount Per Serving: Calories: 303Total Fat: 22gSaturated Fat: 11gTrans Fat: 0gUnsaturated Fat: 9gCholesterol: 15mgSodium: 149mgCarbohydrates: 25gFiber: 2gSugar: 8gProtein: 3g

The nutritional information above is computer-generated and only an estimate.

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