Cinnamon rolls were in regular rotation when I was growing up. There was no clearer sign of Sunday morning than the hollow clink of the cake tin hitting the stove and the assertive pop of a vacuum-packed canister of cinnamon rolls being split open. Arranged casually in a baking dish, they would swell and snuggle in the oven, their giraffe-like pattern of flaky cinnamon topping melting to cover the rolls in a layer of perfectly-engineered sweet spice. They were really more like biscuits than “rolls”—with a questionable ingredient list and wartime-appropriate expiration date—but these were the cinnamon rolls of my youth. And I loved them.
I’ll admit I dabbled with the ‘Bons, their irresistible scent luring my tween posse toward a random alcove of the mall next to the Mrs. Fields. While most of my pals preferred the cinnamon-soaked interior, I liked the drier outer layers drizzled with gooey frosting. But as I grew older I started to find these industrialized rolls unappealing, the icing too sweet, the size intimidating. But that aroma, even after all these years, is still wholly intoxicating.
I wanted to create a more sophisticated cinnamon roll, something more reasonable, appropriately-sized, dare I say, adult. A sweet treat that would still make the house smell like a food court without sending me into an extended sugar coma.
But where’s the fun in that?
So I split the difference. Yes, I came up with cinnamon rolls of a more manageable size and I swapped some of the sugar for maple syrup and sticky sweet dates which offer a complexity that none of the big-box brands can offer. I lost the icing but went instead with a layer of nutty upside-down-cake-inspired brown sugar and butter topping. Make no mistake, these cinnamon rolls are indulgent, but they’re homemade so it’s cool, right? These aren’t necessarily good for you, but they’re good for you.
Note: For extra credit you can make your own dough for these, but a couple of balls of prepared pizza dough work just fine.
Sticky Toffee Cinnamon Rolls
For homemade dough
1 ½ cups warm water
1 tablespoon granulated sugar
2 ¼-ounce packets active dry yeast
4 cups all-purpose flour, plus more for work surface
2 teaspoons kosher salt
For the topping
½ cup packed light brown sugar
4 tablespoons butter
2 tablespoons maple syrup
½ cup chopped pecans, almonds, or walnuts (or a combination)
For the filling
8 tablespoons unsalted butter
8 ounces medjool dates, pitted and chopped
⅔ cup packed light brown sugar
½ teaspoon kosher salt
4 teaspoons cinnamon
How to Make It
Roll and knead your dough. Combine water and sugar in a medium bowl. Sprinkle yeast over top and set aside until foamy, about 5 minutes. Add 4 cups flour and salt, and stir with a wooden spoon until a shaggy dough forms. Turn out onto a lightly floured surface and knead until dough comes together, about 10 times. Lightly oil a medium-sized bowl. Add dough and turn to coat. Cover with plastic wrap and set aside until doubled in size, about 90 minutes.
Prepare the topping. Meanwhile, combine brown sugar, butter, and maple syrup in a 10-inch skillet, preferably cast-iron. Cook, stirring often, until sugar dissolves and mixture is evenly bubbling across the surface, 2 to 3 minutes. Let cool slightly, then sprinkle with nuts. Set aside. If you don’t have a 10-inch skillet, you can do this in whatever skillet you have and then swiftly transfer the toffee mixture to a 10-inch cake pan.)
Fill and assemble. Preheat oven to 350°F. Combine butter, dates, brown sugar, and salt in a medium saucepan and place over medium-high heat. Cook, stirring often, until butter melts. Continue to cook, stirring and mashing to help break up dates, until mixture comes to a boil and dates are broken down, about 4 minutes. Let cool to room temperature.
Once the dough has doubled in size, turn out onto a lightly floured surface. Divide dough in half (this will make it easier to work with) and working with one at a time, roll each piece into a 12- by 16-inch rectangle. Divide date mixture between the two pieces of dough, spreading all the way to the edges. Sprinkle each piece evenly with 2 teaspoons cinnamon. Starting from the long end, roll up dough and place seam-side down. Cut dough crosswise into 2-inch spirals. Transfer rolls, cut sides down, to prepared skillet or cake pan, arranging snugly to fit. Bake until golden and risen, 30 to 35 minutes. Let cool 5 minutes before inverting onto a rack. Let cool slightly before eating.