Cherry Cinnamon Rolls with Homemade Filling

There’s something magical about the aroma of freshly baked cinnamon rolls wafting through the kitchen. It’s one of those scents that instantly creates a feeling of warmth and comfort, bringing everyone to the table with eager anticipation. As a busy parent, I’ve found that few breakfast treats earn quite as many smiles as homemade cinnamon rolls, especially when they’re elevated with the sweet-tart punch of cherries.

Today, I’m sharing my absolute favorite twist on the classic cinnamon roll—Cherry Cinnamon Rolls with completely homemade filling. These aren’t your ordinary breakfast pastries. The addition of cherries creates a gorgeous ruby swirl throughout each roll, balancing the warm spice of cinnamon and adding a fruity brightness that makes these rolls truly special.

While they might seem intimidating at first glance, I promise these cherry-studded beauties are completely doable, even on a weekend morning with little ones underfoot. The dough is forgiving, the filling comes together in minutes, and the end result is so worth the effort. Plus, there’s something deeply satisfying about creating these from scratch that just can’t be matched by anything from a can.

Perfect for Special Occasions

These cherry cinnamon rolls have become my go-to for holiday mornings, weekend brunches when friends come over, and those rare quiet Sunday mornings when we have nowhere to be. They’re special enough for celebrations but comforting enough for everyday indulgence when you need a little something extra to brighten your week.

What makes these rolls truly special is the homemade cherry filling. Rather than using canned pie filling (though that works in a pinch!), I’ll show you how to create a quick cherry filling that’s bursting with fresh flavor. We’ll fold this into a classic cinnamon-sugar mixture to create a filling that’s both familiar and excitingly different.

Ingredients You’ll Need

For the Dough:

• 4 cups all-purpose flour
• 1/3 cup granulated sugar
• 2 1/4 teaspoons (1 packet) active dry yeast
• 1 teaspoon salt
• 1 cup whole milk
• 1/3 cup unsalted butter
• 2 large eggs, room temperature
• 1 teaspoon vanilla extract

For the Cherry Filling:

• 2 cups fresh or frozen cherries, pitted and halved
• 1/3 cup granulated sugar
• 1 tablespoon lemon juice
• 1 tablespoon cornstarch
• 1 tablespoon water

For the Cinnamon Filling:

• 1/2 cup unsalted butter, softened
• 3/4 cup brown sugar, packed
• 2 tablespoons ground cinnamon
• 1/4 teaspoon salt

For the Cream Cheese Glaze:

• 4 ounces cream cheese, softened
• 2 tablespoons unsalted butter, softened
• 1 cup powdered sugar
• 1-2 tablespoons milk
• 1/2 teaspoon vanilla extract
• Pinch of salt

Essential Equipment

Step-by-Step Instructions

Making the Dough

1. In the bowl of your stand mixer, combine 2 cups of flour, sugar, yeast, and salt. Mix briefly to combine.
2. In a small saucepan, heat the milk and butter over medium-low heat until the butter is melted and the mixture reaches about 110°F (warm but not hot). If it gets too hot, let it cool slightly—we don’t want to kill the yeast!
3. Pour the warm milk mixture into the flour mixture. Add the eggs and vanilla.
4. With the paddle attachment, mix on low speed until combined, then increase to medium speed and beat for 2 minutes.
5. Switch to the dough hook and gradually add the remaining 2 cups of flour, 1/2 cup at a time, until the dough forms a soft ball and pulls away from the sides of the bowl. You might not need all the flour—the dough should be soft and slightly tacky, but not sticky.
6. Knead on medium-low speed for 5-6 minutes until the dough is smooth and elastic.
7. Place the dough in a large greased bowl, turning once to coat the top. Cover with plastic wrap or a clean kitchen towel and let rise in a warm place for about 1 hour, or until doubled in size.

Preparing the Cherry Filling

While the dough rises, let’s make the cherry filling:

1. In a medium saucepan, combine the cherries, sugar, and lemon juice. Bring to a simmer over medium heat.
2. Cook for about 5 minutes, until the cherries begin to break down and release their juices.
3. In a small bowl, whisk together the cornstarch and water to create a slurry.
4. Stir the cornstarch slurry into the simmering cherries and cook for an additional 1-2 minutes, until the mixture thickens.
5. Remove from heat and allow to cool completely. (You can speed this up by transferring to a bowl and refrigerating.)

Making the Cinnamon Filling

1. In a medium bowl, mix together the softened butter, brown sugar, cinnamon, and salt until well combined and smooth. Set aside.

Assembly

1. Once the dough has doubled in size, punch it down gently and turn it out onto a lightly floured surface.
2. Roll the dough into a large rectangle, approximately 18×14 inches. The dough should be about 1/4 inch thick.
3. Spread the cinnamon filling evenly over the surface of the dough, leaving a 1/2-inch border along one long edge.
4. Spoon the cooled cherry filling over the cinnamon mixture, spreading it as evenly as possible.
5. Starting with the long edge (opposite from the one with the border), tightly roll the dough into a log shape.
6. Using a sharp knife or dental floss, cut the log into 12 equal pieces, each about 1.5 inches thick.
7. Arrange the rolls in a greased 9×13 inch baking dish, leaving a little space between each for rising.
8. Cover with plastic wrap or a kitchen towel and let rise again for about 30-45 minutes, until puffy and nearly doubled.

Baking

1. Preheat your oven to 350°F (175°C) during the final 15 minutes of rising time.
2. Once the rolls have risen, bake for 25-30 minutes, until golden brown on top and cooked through. If they start to brown too quickly, tent loosely with aluminum foil.
3. Remove from the oven and allow to cool slightly while you prepare the glaze.

Making the Cream Cheese Glaze

1. In a medium bowl, beat together the cream cheese and butter until smooth and creamy.
2. Gradually add the powdered sugar, mixing well after each addition.
3. Stir in the vanilla extract and salt.
4. Add milk, 1 tablespoon at a time, until you reach your desired consistency. For a drizzle, you’ll want it a bit thinner; for a frosting, keep it thicker.
5. Spread or drizzle the glaze over the slightly warm rolls.

Serving Suggestions

Serve these delicious cherry cinnamon rolls warm from the oven for maximum enjoyment. They pair beautifully with:

• A steaming mug of coffee or hot chocolate
• Fresh fruit on the side
• A dollop of vanilla yogurt for a tangy contrast
• A sprinkle of toasted almonds for crunch
• For special occasions, add some fresh cherries on top as a garnish

Make-Ahead Options

I know mornings can be chaotic, especially with kids, so here are some ways to prepare these rolls in advance:

Overnight Method

1. Prepare the rolls through the cutting and arranging in the baking dish step.
2. Cover tightly with plastic wrap and refrigerate overnight (up to 12 hours).
3. In the morning, remove from the refrigerator and let stand at room temperature for 30-45 minutes before baking as directed.

Freezer Method

1. Prepare and bake the rolls completely, but don’t add the glaze.
2. Allow to cool completely, then wrap tightly in plastic wrap and aluminum foil.
3. Freeze for up to 2 months.
4. Thaw overnight in the refrigerator, then reheat in a 300°F oven for about 10-15 minutes until warmed through.
5. Prepare the glaze fresh and add just before serving.

Troubleshooting Tips

Variations to Try

While these cherry cinnamon rolls are absolutely divine as written, don’t be afraid to experiment with these delicious variations:

Mixed Berry

Substitute a mixture of blueberries, raspberries, and blackberries for the cherries. The combination creates a gorgeous purple-hued filling.

Cherry Almond

Add 1/2 teaspoon of almond extract to the dough and sprinkle 1/4 cup of sliced almonds over the filling before rolling.

Orange Cherry

Add the zest of one orange to the dough and a tablespoon of orange juice to the glaze for a citrusy twist.

Dark Chocolate Cherry

Sprinkle 1/2 cup of mini dark chocolate chips over the cherry filling before rolling for an indulgent chocolate-cherry combination.

Whole Wheat Option

Replace up to half the all-purpose flour with whole wheat flour for a slightly nuttier, more wholesome roll. You may need to add a bit more liquid.

Storage and Reheating

These cherry cinnamon rolls are best enjoyed fresh on the day they’re baked, but if you have leftovers:

• Store at room temperature in an airtight container for up to 2 days.
• Refrigerate for up to 5 days (they will firm up in the fridge).
• To reheat, microwave individual rolls for 20-30 seconds, or place multiple rolls in a 300°F oven for 10 minutes until warmed through.

Nutritional Information

Note: Nutritional values are estimates and may vary based on specific ingredients used.

Why This Recipe Works

What makes these cherry cinnamon rolls so special comes down to a few key factors:

1. The Dough: This dough has the perfect ratio of fat to flour, creating a tender roll that stays soft even the next day.
2. Homemade Cherry Filling: By making our own cherry filling, we control the sweetness and consistency, avoiding the cloying sweetness and artificial flavor that can come with canned fillings.
3. The Cinnamon-Cherry Combination: The warmth of cinnamon perfectly balances the bright, fruity notes of the cherries for a flavor profile that’s complex and satisfying.
4. The Tanginess: Both the cherries and the cream cheese glaze provide tangy notes that cut through the sweetness, creating a balanced treat that isn’t overwhelmingly sugary.

Frequently Asked Questions

Q: Can I use canned cherry pie filling instead of making my own?

A: Absolutely! If you’re short on time, you can substitute about 1 1/2 cups of canned cherry pie filling. Just be aware that it will be sweeter and not quite as fresh-tasting.

Q: What if cherries aren’t in season?

A: Frozen cherries work beautifully in this recipe and are often more convenient since they’re already pitted. Just thaw and drain them before using.

Q: Can I make these without a stand mixer?

A: Yes! You can mix the dough with a wooden spoon and then knead by hand on a floured surface for about 8-10 minutes until smooth and elastic.

Q: How do I know when the rolls are done baking?

A: The tops should be golden brown, and if you insert a thermometer into the center of a roll, it should read about 190°F. Another way to check is to gently pull at the center roll—if it still looks doughy and raw, they need more time.

Q: Can I halve this recipe?

A: Yes, you can make a half batch in an 8×8 or 9×9 inch pan. All ingredient amounts can be halved directly, though you may want to still use a whole egg for the dough.

Q: What’s the best way to cut the rolls?

A: Unflavored dental floss works amazingly well! Slide it under the roll, cross it on top, and pull—you’ll get a clean cut without squishing the roll. A very sharp knife works too.

Q: Can I make these gluten-free?

A: While I haven’t tested this recipe with gluten-free flour, readers have reported success using a 1:1 gluten-free flour blend. The texture may be slightly different, and you might need to adjust the liquid slightly.

Final Thoughts

There’s something truly special about taking the time to create something like these Cherry Cinnamon Rolls from scratch. In our busy lives, slowing down to knead dough, create a filling, and wait patiently through rising times can feel like a small act of rebellion against the constant rush.

When I pull these rolls from the oven and see my family’s faces light up, I’m reminded that these kitchen moments—hands dusted with flour, the rhythmic motion of rolling dough, the anticipation of something wonderful—are creating memories that will last far longer than the rolls themselves (which, let’s be honest, disappear pretty quickly!).

I hope these cherry-studded cinnamon rolls bring as much joy to your kitchen as they have to mine. There’s nothing quite like watching someone take that first bite and seeing their eyes close in appreciation of something made with love.

Happy baking!