Recipe: Milk Chocolate Ice Cream Sandwiches

Before I moved to Maine, I’d never lived such a seasonal life. I grew up in Central California, where we argued that the seasons were obvious for those that didn’t need to be hit over the head with plagues of insects or bad weather. My mom was from upstate New York, and remained diplomatically silent while my California-born siblings and I celebrated the first day of spring by getting a sunburn at the beach, and bemoaned winter because we had to wear a raincoat. 

When my husband Steve and I were planning our move to Maine, people who knew told me about the snow and the ice and the mosquitos and the lobsters and the foliage. But they never mentioned how much my household and my habits would shift because of these things. That I would change out my entire closet of clothes two times a year. That I would bank my house with spruce boughs in the fall. That there was an actual thing called a mud room. And that my summers would be spent hosting hordes of family and friends, and giving directions to passing tourists. 

We went into the chocolate business because we needed a way to make a living in one of the east coast’s more remote outposts. Paid wintertime work is pretty scarce on a fishing island 7 miles off the coast of Maine, but our research showed that the busiest time for chocolate makers was between Halloween and New Year’s. Our research also said that the slowest time for chocolate sales was the summer, and having fallen in love with this perfect, fleeting season, that suited us just fine. 

After ten years in the biz, I can tell you with some authority, that the people who came up with those theories were not from Maine. While many small chocolatiers stop shipping in the summer, and some even shut their doors altogether in the dog days of July and August, Maine chocolatiers celebrate their anomaly status by fueling the tourist population with sweet treats and coveted gifts for the cat sitters and neighbors back home.  

As a featured ingredient, chocolate is always in season. It’s a universal truth employed by restaurant chefs and home entertainers alike. A successful menu, no matter how inspired by what’s in the farmers’ markets, will  include a chocolate dessert. Not only is it universally appealing, but chocolate is almost always attached to some kind of happy nostalgia.

Each summer, I plan my own menu; three days worth of meals that I can serve weekend after weekend, to the rotating posse of out of state house guests and friends vacationing in the area. This frees me up from weekly menu planning, and gives me more time to visit and enjoy my own summer. The meals aren’t necessarily simple—after all, I like to cook—but they must be universally appealing, repeatable, and interesting enough that I don’t get bored. And they must of course include chocolate.

These  Milk Chocolate Ice Cream Sandwiches are meant to be made ahead of time, and enjoyed around a backyard fire pit, perhaps along with roasted marshmallows. Or taken from a cooler at a Fourth of July block party. The rich shortbread will soften slightly once it is sandwiched and frozen with the ice cream center, and that’s what you want—a gourmet-esque dessert subtly reminiscent of the convenience store freezer treats of childhood.

Milk Chocolate Ice Cream Sandwiches

Makes 9 sandwiches

These ice cream sandwiches look delightfully old school and carefree, but they do require a plan. Here it is: 

1. Make the ice cream custard before you go to bed, so that you can allow it to chill overnight in the refrigerator. This strategy is great if you’re like me and tend to jump the gun when you want ice cream NOW. Chilling the custard completely while you sleep, allows for 100% obsessive-free wait time. 
2. Freeze the ice cream in your ice cream maker the next morning, and allow it to harden in the freezer while you make your shortbread. By the time the shortbread is baked, cooled, and ready to fill, your ice cream will likely be at exactly the right consistency. 
3. If you’re taking these guys on an (insulated) adventure, you’re going to need another overnight freeze for your wrapped ice cream sandwiches to harden. 
4. Here’s another helpful tip: if you want 18 sandwiches, just double the shortbread recipe. 

For the ice cream:

1-1/2 cups heavy cream

1-1/2 cups whole milk

½ cup granulated sugar

2 large eggs

8 ounces good quality milk chocolate, chopped

½ teaspoon vanilla extract

For the shortbread:

1 cup butter, softened

1 teaspoon salt

¾ cup granulated sugar

1 tablespoon instant espresso powder, like Medaglia D’Oro (optional)

1-3/4 cups all-purpose flour

¼ cup cocoa powder

To make the ice cream:

1. Place the cream and milk into a medium-sized sauce pan, and bring to a boil over a medium flame. 
2. While the cream is heating, crack the eggs into a heat proof bowl and whisk them thoroughly with the sugar. 
3. Place the chopped chocolate into a separate heat proof bowl.
4. When the cream comes to a boil, remove the pan from the heat, and pour very slowly into the egg mixture, while whisking. 
5. Next, pour the hot cream/egg mixture through a sieve over the chopped chocolate. Allow this to sit for a minute or two, then whisk until perfectly smooth. Stir in the vanilla extract. 
6. Cover the bowl with plastic wrap and chill the custard thoroughly. 
7. When the custard is chilled, freeze in an ice cream maker according to the manufacturer’s instructions. 
8. When the ice cream is frozen, scrape it into a container, cover with plastic wrap, pressing the plastic directly to the surface of the ice cream (this will prevent ice crystals from forming), then place the cover on the container, or cover with one more layer of plastic wrap. Place in the freezer. 

To make the shortbread:

1. Heat your oven to 350 degrees.
2. In a stand mixer with the paddle attachment, or with an electric hand-held beater, cream the butter with the salt and sugar until it is very smooth and homogenous. Beat in the espresso powder, if using. Then add the flour and cocoa powder all at once. 
3. Beat until the mixture is cohesive, and no dry flour remains. The dough should be very soft. Divide the dough equally in two. 
4. Line an 11” x 18” cookie sheet with parchment.  Press each ball of dough into a rough 9” x 6” rectangle on the cookie sheet. They don’t have to look perfect. Prick the dough all over with a fork. 
5. Bake for 15 minutes, or until the cookie is dry, but not too hard. Remove from the oven and allow to cool completely. 

To assemble the ice cream sandwiches:

1. When the ice cream is slightly more frozen than when it came out of the ice cream maker, but not hard, remove it from the freezer (depending on your freezer, this may take anywhere from an hour to several hours). 
2. Turn over one sheet of your cooled shortbread so that the flat side faces up. Spread roughly half of the ice cream onto the surface of the shortbread, spreading it to about ½ inch from the edges. Place the other rectangle of shortbread, flat side down, on top of the ice cream. Wrap the entire thing tightly in plastic wrap and freeze until hard. The ice cream will squeeze out to the edges, and that’s what you want it to do. 
3. When ready to serve or pack up for later, remove this ginormous ice cream sandwich from the freezer, unwrap, and with a large, sharp chef’s knife, cut into 9 3” x 2” bricks. Serve immediately. Or, to serve later, wrap in parchment, securing the paper with twine or tape, and store in the freezer, or take them wherever you’re going in a well-insulated ice chest.