This month, Erica invited our cooking club to explore the theme “Quintessential San Francisco” during one of our epic four-hour eating fests. The meal did not disappoint: sourdough bread made from scratch, bay shrimp salad, an Alice Waters-inspired goat cheese souffle, and a hearty cioppino with lots of fresh seafood, including (of course) Dungeness crab.
I signed up for dessert duty and took my inspiration from the classic San Francisco treat I fell in love with when I first moved here years ago. No, I’m not talking about Rice-a-Roni (but wouldn’t that be an interesting dessert challenge?). I’m talking about “It’s It” ice cream sandwiches: vanilla ice cream sandwiched between two oatmeal cookies and dipped in chocolately goodness. Developed in 1928 at Playland-at-the-Beach (San Francisco’s version of Coney Island), and still available at any respectable corner store in SF.
I didn’t want to drift too far from the original combination–why mess with a good thing?–but I did dress it up a bit. This is cooking club after all, which is nothing if not over-the-top. After a little rummaging around in the spice cabinet, I ended up with a creation that was sort of like It’s It‘s sassier granddaughter. And It was good. Damn good. Which is why I feel compelled to share the recipe with you.
I’m not gonna lie. This was an all-weekend commitment. If you’re looking for quick and easy, you’re better off getting your It’s It at the corner store. But if you like an excuse to spend the day making a big mess in your kitchen, and licking all kinds of yummy spoons along the way, It’s totally worth It.
“It’s It” Vanilla Bean Ice Cream Sandwiches with Oatmeal Molasses Spice Cookies, Dipped in Mexican Chocolate
Step 1: Make your ice cream custard (see vanilla bean ice cream recipe below), and stick it in the fridge to chill. I chose to make vanilla bean ice cream, but I have to admit, once it was all said and done, the other flavors kinda stole the spotlight, so I’m not sure it’s worth wasting two expensive vanilla beans for this recipe. You might be better off with a simple vanilla ice cream, made with extract. But I’ll leave that up to you. Vanilla bean certainly sounds fancier, for when that sort of thing matters.
Step 2: Make cookies (see recipe below). I experimented with the cookie recipe. I looked up a bunch of recipes and then more or less decided to do my own thing. I thought that using molasses might help keep the cookies soft when frozen. I’m not really sure if that worked, but I did like the flavor. Kind of like a cross between an oatmeal and a ginger cookie. The dough really spread out a lot on the cookie sheets while baking, so I used a 3″ cookie cutter to trim all the cookies into uniform circles. I can be obsessive compulsive like that sometimes. If you’re going the OCD route, it’s easiest to do while the cookies are still a little warm. And you can save the cookie scraps to munch on or crumble over ice cream. (As if you’ll need any extra calories after devouring a chocolate-dipped ice cream sandwich or two…or three.)
Step 3: Freeze ice cream custard in your ice cream maker. BTW, don’t forget–like I did–to put the bowl of your ice cream maker in the freezer the day before you want to use it. Oops. Any sane person probably would have said “oh well, I guess I’ll use store-bought ice cream.” But not me. My Martha Stewart gene kicked in and I was up until 12:30 am making ice cream sandwiches.
Step 4: Assemble sandwiches. I didn’t measure, but I’d guess that I put about 1/3 cup of ice cream in each sandwich. Next time, I’d put a little more, since I had plenty left over and the proportions of the final sandwich leaned a little too far in the cookie/chocolate direction. Wrap them up in plastic and freeze at least 3 hours, or overnight. I devised a little system to keep the ice cream from oozing out too much that–depending on how you look at it–was either incredibly anal (see Martha Stewart gene above) or incredibly lazy (because it was after midnight and I didn’t want to wait for my soft ice cream to harden up in the freezer). Regardless of your verdict on my motive, it worked incredibly well, and it went a little something like this: I took ramekins that were 3.5″ in diameter and 3″ deep, and lined them with plastic wrap, leaving a generous amount of plastic hanging over the sides. As I assembled each sandwich, I placed it into the ramekin, put a little wax paper in between, and then layered another sandwich on top (2 sandwiches in each ramekin). Then I closed the plastic wrap tightly over the top and stuck the ramekins in the freezer as I filled each one. This allowed me to get the sandwiches into the freezer faster as I worked, and it was also much easier to make room in my freezer than if all the sandwiches were on one tray.
Step 5: Make the Mexican chocolate coating.
20 oz. bittersweet chocolate chips (I used Ghirardelli, of course!)
6 oz. milk chocolate chips
2 tablespoons vegetable shortening
1 teaspoon cinnamon
1/4 teaspoon sea salt
dash cayenne pepper
Melt the chocolate and shortening in a deep saucepan over very low heat, stirring constantly. Add spices and stir. As soon the mixture is smooth and melted, remove from the heat and set aside, letting it slowly come to room temperature.
Step 6: Time to dip! This is the fun/messy part. I looked at a few different references for technique, and the idea of adding shortening to the chocolate, but relied most heavily on Merill’s recipe for Mint Chocolate Harbor Bars on Food52.
Get a baking sheet that will fit in your freezer and line it with wax paper. Working with one sandwich at a time (keep the rest in the freezer), place the sandwich onto a slotted spoon and lower it into the melted chocolate. Turn the sandwich over with your fingers and lower it back into the chocolate to coat the whole sandwich evenly, and then lift it out with the spoon, letting the excess chocolate drip off. Transfer sandwich to the baking sheet and quickly repeat with the remaining sandwiches. Immediately return the sandwiches to the freezer until the chocolate sets, at least 15 minutes.
At this point in the recipe, me and my entire kitchen were covered in chocolate. It wasn’t pretty. All my sandwiches had little white finger prints where the chocolate didn’t cover and the ice cream was peeking out, so as soon as the chocolate covering hardened up a little, I re-dipped the bald spots. They looked pretty goopy gloppy, like a kindergarten art project, and my Martha Stewart side worried that I’d be kicked out of my cooking club. But in the end it didn’t matter. It just made them look legitimately homemade, and they were so damn delicious that nobody seemed to mind the fingerprints. It didn’t hurt that we were in the middle of a glorious mini-heat wave in San Francisco, and ice cream sandwiches seemed just the right thing to do.
Vanilla Bean Ice Cream
Makes about 1 1/2 quarts
2 vanilla beans
3 cups heavy cream
1 cup whole milk
1 1/2 cups sugar
3 large eggs
Cut vanilla beans in half lengthwise. Scrape seeds into a large heavy saucepan and stir in pods, cream, milk, and sugar. Bring mixture just to a boil, stirring occasionally, and remove pan from heat.
In a large bowl lightly beat eggs. Add hot cream mixture to eggs in a slow stream, whisking, and pour into pan. Cook custard over moderately low heat, stirring constantly, until custard is thick enough to coat the back of a wooden spoon. (About 10-15 min.) Pour custard through a sieve into a clean bowl and cool. Chill custard, its surface covered with wax paper, at least 3 hours, or until cold, and up to 1 day.
Freeze custard in an ice-cream maker. Transfer ice cream to an airtight container and put in freezer to harden up slightly (30-60 min)—it will be easiest to assemble sandwiches while ice cream is still slightly soft. But the ice cream can be made up to one week ahead and stored in the freezer in an airtight container (ditto for any leftover ice cream). If you make the ice cream ahead of time, simply remove from the freezer and allow it to soften up a bit before you assemble the sandwiches.
Oatmeal Molasses Spice Cookies
Makes about 3 dozen.
1/2 lb (2 sticks) unsalted butter, softened
1 cup granulated sugar
½ cup molasses
2 large eggs
1-3/4 cups all-purpose flour
1/4 teaspoon salt
1 teaspoon baking soda
1 ½ teaspoon ground cinnamon
1 teaspoon ground cardamom
1 teaspoon ground ginger
1 teaspoon dried ground orange peel (I happened to have this in my spice cabinet, so I threw some in. I’m sure you could use fresh orange zest—I would do ½ tsp.—or skip this ingredient)
½ teaspoon ground nutmeg
½ teaspoon ground allspice
½ teaspoon ground white pepper
3 cups whole rolled oats (old-fashioned)
Pre-heat oven to 350° F. Cream together the butter, sugar, and molasses in a large mixing bowl. Beat in eggs until well blended.
In a small mixing bowl, stir together flour, salt, baking soda, and all the spices. Add dry ingredients to butter mixture and mix until well combined. Fold in oats with a wooden spoon or sturdy rubber spatula.
Line baking sheets with parchment paper. Scoop dough onto the paper in spoonfuls, spacing them about 2 inches apart. They will spread quite a bit while baking.
Bake until cookies are golden but centers are still soft, about 10 minutes. Remove from oven and let them sit on the baking sheet for a few minutes to cool.