Apple Pie Cinnamon Rolls With Cream Cheese Frosting

Fall is my season. I've said this before and I'll say it again because repetition is how you build a brand and apparently I have a brand now. Fall in Milwaukee: the leaves turn. The air cools. The beer gets darker. The soup gets thicker. Everything that matters about this city comes into focus between September and November.

The Oktoberfest is back on tap. This year I adjusted the recipe slightly — more Munich malt for a richer bread note, a touch less hop bitterness, longer lagering time. The result is the smoothest Oktoberfest I've made. Tom tasted it and said the thing he says every year: "This is the best one yet." He means it every year. I believe him every year.

Megan and I went apple picking this weekend. Cedarburg, about thirty minutes north of the city. She wore a flannel shirt and boots and looked like a magazine ad for fall and I wore the same jeans I wear every day and looked like a guy who owns a Jeep. We picked Honeycrisp apples — the only apple worth picking, and I will fight anyone who says otherwise — and came home with two bushels that will become apple pie, apple crisp, apple sauce, and the apple cinnamon pierogi I invented last year.

Made apple crisp that night. Simple: sliced apples tossed with cinnamon, sugar, and lemon juice in a baking dish, topped with a crumble of oats, brown sugar, butter, and flour. Baked until the top is golden and the apples are bubbling. Served warm with vanilla ice cream. Megan ate two servings and said, "This is my love language." I said, "I thought your love language was nachos." She threw an apple at me.

Tom called about the deck. He wants to restain it before winter. He asked if I'd help next Saturday. I said yes. We'll spend the day with sandpaper and stain and very few words and it will be perfect.

The apple crisp was gone by morning — Megan saw to that — but we still had nearly two bushels of Honeycrisp left and a Sunday with nowhere to be. Apple crisp is the weeknight move; what I really wanted was something that required a little more patience, something that filled the apartment with that cinnamon-apple smell for a couple of hours while the Oktoberfest conditioned in the basement. These apple pie cinnamon rolls are the answer to that impulse: all the flavors of the apple crisp, wrapped in soft dough and finished with cream cheese frosting that has no business being as good as it is. Make them on a slow fall morning. You’ll thank yourself.

Prep Time: 30 min | Cook Time: 25 min | Total Time: 2 hr 15 min (includes rise time) | Servings: 12

Ingredients

Dough
3/4 cup warm whole milk (about 110°F)
2 1/4 tsp active dry yeast (1 packet)
1/4 cup granulated sugar, divided
2 large eggs, room temperature
1/3 cup unsalted butter, melted
1 tsp kosher salt
4 cups all-purpose flour, plus more for dusting
Apple Pie Filling
3 cups Honeycrisp apples (about 3 medium), peeled and finely diced
1/4 cup unsalted butter
1/2 cup packed brown sugar
2 tsp ground cinnamon
1/4 tsp ground nutmeg
1 tbsp lemon juice
1 tbsp cornstarch
Cream Cheese Frosting
6 oz cream cheese, softened
1 1/2 cups powdered sugar, sifted
3 tbsp whole milk
1 tsp pure vanilla extract
Pinch of salt

Instructions

Activate the yeast. Combine warm milk, yeast, and 1 tbsp of the granulated sugar in the bowl of a stand mixer. Stir gently and let sit 5–10 minutes until foamy and fragrant.
Make the dough. Add eggs, melted butter, remaining sugar, and salt to the yeast mixture. Using the dough hook, mix on low. Add flour one cup at a time, mixing until a soft, slightly tacky dough forms. Increase speed to medium and knead 6–8 minutes until smooth and elastic.
First rise. Shape dough into a ball and place in a lightly greased bowl. Cover with plastic wrap and let rise in a warm spot until doubled in size, about 1 to 1 1/2 hours.
Cook the apple filling. While dough rises, melt butter in a medium skillet over medium heat. Add diced apples, brown sugar, cinnamon, nutmeg, and lemon juice. Cook 5–7 minutes, stirring occasionally, until apples soften. Stir in cornstarch and cook 1 minute more until filling thickens slightly. Remove from heat and let cool completely.
Roll and fill. Punch down risen dough and turn out onto a lightly floured surface. Roll into a 12x18-inch rectangle. Spread cooled apple filling evenly over the dough, leaving a 1/2-inch border along one long edge.
Roll and cut. Starting from the filled long edge, roll the dough tightly into a log. Pinch the seam to seal. Using a sharp knife or unflavored dental floss, cut into 12 equal rolls.
Second rise. Arrange rolls cut-side up in a greased 9x13-inch baking dish. Cover loosely and let rise 30–45 minutes until puffed and touching.
Bake. Preheat oven to 350°F. Bake rolls 22–26 minutes until golden brown on top and set in the center. Do not overbake — they should still look slightly soft.
Make the frosting. Beat softened cream cheese with a hand mixer until smooth. Add powdered sugar, milk, vanilla, and salt; beat until creamy and spreadable, 2–3 minutes.
Frost and serve. Spread cream cheese frosting generously over warm rolls. Serve immediately and watch them disappear.

Nutrition (per serving)

Apple Pie Cinnamon Rolls With Cream Cheese Frosting — When Two Bushels of Honeycrisp Call for Something Extra