Apple Pear Cinnamon Rolls with Bourbon Glaze (Gluten-Free Option)
Originally posted October 2021. Updated August 2026.
Cinnamon rolls hold an incredibly special place in my heart because my mom always made them for Christmas morning. She’d start them a day or two ahead. And then we’d wake up and open presents, while the cinnamon rolls baked in the oven. After presents, we’d eat warm, fluffy cinnamon rolls for breakfast or early brunch. Soooo, freaking good and always brings back those warm memories. It’s memories like that, that inspired this recipe for Apple Pear Cinnamon Rolls with Bourbon Glaze.
These bad boys are pure fall flavors. Good for the whole family (if you leave the bourbon out of the glaze) but quite honestly, they are adult flavors. Apples and pears rolled up in a fluffy yeasty dough and baked until they are crispy tender and golden brown. Then topped while warm with an ooey gooey Brown Sugar and Bourbon glaze, crunchy candied pecans, and fennel seeds. YES, PLEASE! I’m drooling right now.
So, why bourbon? Because nothing speaks of fall like bourbon. And bourbon in baked goods combined with fall fruits and nuts, even better, which is why you also don’t want to miss my recipe for Bourbon Pumpkin Gingerbread Bundt Cake.
Picking the Right Apples and Pears for these Cinnamon Rolls
Crunchy, slightly tart apples and firm, not soft, pears are a MUST for this recipe. Sweet apples are a no go for these rolls. Same with the pears. If they are ripe and soft then they overcook to mush during baking. You want them to hold shape.
Personally, my favorite apple is the Honeycrisp or Winesap (hard to find but amazing heirloom apple variety). They are crunchy, slightly tart, and just perfect for these cinnamon rolls. Pink Ladies and Galas also work. I used Galas in this recipe because they just came into season. And of course you could use the Granny Smith. I know it’s a favorite for a lot of people, but not mine. It’s a bit tart and acidic without a balance of sweet to balance the taste. Avoid any apple that is soft and mealy.
On the pears, most any will do as long as they aren’t ripe. This is one recipe when you want them still to be hard and crunchy. The baking turns them into perfectly soft, still holding their shape. The key is one that has a nice flavor when they are ripe. Some pears are mostly tasteless. Tasteless is not what we’re looking for these Apple Pear Cinnamon Rolls with Bourbon Glaze.
What are the Best Nuts for Apple Pear Cinnamon Rolls with Bourbon Glaze
Pecans are the way to go for the best flavor combination on these cinnamon rolls. These cinnamon rolls are based entirely on Southern flavors. It’s my Southern US roots showing up. And pecans are a natural pairing for bourbon and brown sugar. They’re my first choice with the fennel seed. But bitter walnuts also work nicely in this combo.
Toasted pine nuts could also work or pistachios. Almonds or peanuts aren’t quite the right flavor for this one.
Apple and Pear Cinnamon Rolls Gluten-Free Option
If you’re using Bob’s Red Mill All-Purpose Gluten-Free Flour, you can substitute equal amounts for the all-purpose flour in this recipe. As far, as other gluten-free flours, I’m not sure. You’ll have to evaluate and trial it out to see. But Bob’s version works beautifully in this recipe for all my gluten-free friends to bring a similar texture and taste.
Additions
Two additions I want to try for this recipe are to add red pepper chili flakes and crispy BACON (can you ever go wrong with bacon, bourbon and brown sugar together?). Just cook the bacon crispy and then crumble the chili flakes and bacon in with the candied pecans and fennel seeds. They’ll both be absolutely delicious with the Brown Sugar Bourbon Glaze.
Make-Ahead and Storage
The best part about cinnamon rolls is pulling them warm from the oven — and the second-best part is doing all the work the night before so you actually can. These are made for a holiday morning.
To make ahead: assemble the rolls all the way through shaping and their second rise, then cover and refrigerate overnight. In the morning, pull them out, let them come to room temperature and finish rising for 30 to 45 minutes, and bake. Fresh, warm rolls without the 5 a.m. dough wrangling — exactly what you want on Christmas morning or Thanksgiving.
To store leftovers: keep them covered at room temperature for a couple of days, or in the fridge for up to five. A quick 10 to 15 seconds in the microwave brings them right back to ooey-gooey.
To freeze: freeze them shaped but unbaked (thaw overnight in the fridge, then rise and bake), or freeze them fully baked with the glaze kept separate and drizzled after warming. Baked-and-frozen rolls keep about a month.
Fall fruits and spices just make for beautiful flavors in cinnamon rolls. Pears and apples in these, and if you fancy pumpkin ones, try my recipe for Pumpkin Ginger Cinnamon Rolls another fall cinnamon roll worth the weekend (use the extra pumpkin to make a ginger forward pumpkin pie).
What’s your favorite topping for cinnamon rolls? Are you a traditional fan for a powdered sugar or cream cheese topping with just cinnamon on the inside? Or do you like something else?
Let me know in the comments. And if you have questions, please let me know.
RECOMMENDED INGREDIENTS & TOOLS
- Active Dry Yeast — Fresh yeast is the whole game. Old yeast makes dense rolls. Check the date.
- Whole Pecans — Buy whole and chop your own for the candied topping; pre-chopped go stale and lose the crunch.
- Whole Fennel Seed — The unexpected star of the topping. Worth keeping in the pantry.
- Bob’s Red Mill 1-to-1 Gluten-Free Flour — Your named GF sub that works; link it.
- Stand Mixer with Dough Hook — This enriched dough is sticky; the hook does the kneading.
- 9-inch pie plate — Classic size for the full batch.
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FAQ
- Do I have to use bourbon in the glaze? No. Hard apple or pear cider will work nicely. Or you can make the alcohol free by swapping in apple cider or milk plus a splash of vanilla. You lose the caramel-bourbon depth but still have a lovely glaze that goes well with these cinnamon rolls.
- Why fennel seed in the topping? Okay, I wouldn’t skip the fennel seed in this one because that pop of gentle toasted anise note against the bourbon and fall fruits is just amazing. But totally up to you, if you’re not a fan to leave them out.
- Can I make these gluten-free? Absolutely. Bob’s Red Mill 1to 1 gluten-free flour to my go to for making any flour based baked dish gluten free. You can use equal parts with no fancy ingredients needs. I will say the dough is slightly more delicate, but it all comes out nicely. Chill it briefly before rolling if it’s feeling too sticky.
Apple Pear Cinnamon Rolls with Bourbon Glaze (Gluten-Free Option)
Ingredients
Dough Ingredients
- 1 cup lukewarm milk
- 2.5 tsp active dry yeast
- 1 tbsp dark brown sugar
- 4 tsbp butter melted
- 3 large eggs
- 1.5 tsp salt
- 4.5-5 cups all-purpose flour
- 1 tsp fresh ground black pepper
Apple and Pear Filling
- 3 small Honeycrisp or Gala apples sweet tart
- 1 large pear ripe, but not soft
- ½ cup dark brown sugar
- ¼ cup white sugar
- 4 tsp cinnamon
- pinch salt
- 6 tbsp butter room temperature
Candied Pecans and Fennel Seeds
- 1 tbsp whole fennel seeds
- 1 cup pecans roughly chopped
- 1 tsp fresh ground black pepper
- 1 tsp cinnamon
- ½ tsp salt
- 2 tbsp butter melted
- 3 tbsp bourbon
- 3 tbsp dark brown sugar
Brown Sugar Bourbon Icing
- 1 cup cream cheese room temperature
- 4 tbsp butter
- ¼ cup dark brown sugar
- 4 tbsp bourbon
- 2 tsp vanilla
- pinch salt
- 1.5-2 cups powdered sugar
- ½ tsp fresh ground black pepper
Instructions
Dough Ingredients
- Combine lukewarm milk, yeast, and brown sugar in a large bowl and let sit until bubbly – about ten minutes.
- Using a dough hook on a stand mixer or stir by hand melted butter, salt, eggs, and four cups of flour until completely incorporated. Add more flour as needed until dough is tacky and smooth but not sticky – between five and ten minutes.
- Remove dough ball and lightly oil bowl. Then cover with plastic wrap and allow to rise until dough has doubled – about one hour.
- Meanwhile, prepare the Apple and Pear Filling and Candied Pecans and Fennels Seeds
Apple and Pear Filling
- Peel and finely chop apples and pear. Mix and set aside.
- In a small bowl, combine butter, brown and white sugar, cinnamon, black pepper, and salt, until smooth
Candied Pecans and Fennel Seeds
- In a small pot, over medium heat, toast pecans and fennels seeded until lightly toasted, being careful not to burn. Remove from pan.
- Add butter to pan with bourbon, brown sugar, cinnamon, salt, and black pepper. Cook until alcohol has reduced by half – two to three minutes.
- Add toasted pecans and fennel seeds, stirring to coat.
- Pour mixture out onto baking paper to cool. Once cool, crumble and put aside until topping the cinnamon rolls.
Preparing Dough for Baking
- Lightly butter a 9×13 inch baking dish or two smaller dishes.
- Punch the dough down and then roll out on a lightly floured surface, creating a 15 x 21-inch rectangle.
- Using a spatula, evenly spread butter mixture over flour. Sprinkle evenly with chopped apples and pear.
- Starting with the edge closest to you, tightly roll dough up, pinching edges to seal.
- Using a sharp knife or piece of unflavored dental floss, cut the dough into 14 rolls – approximately 1/2-3/4 inch thick.
- Place rolls into prepared baking dishes. Cover with plastic wrap and allow to rise until doubled – 30 to 45 minutes.
- Preheat oven to 350°F (175°C).
- Bake for 25 to 30 minutes, or until golden brown.
- While rolls are baking, prepare Bown Sugar Bourbon Icing
Brown Sugar Bourbon Icing
- In small pan, heat butter over medium heat. Cook until butter is browned and smelling slightly nutty in flavor. Be careful not to burn.
- Add brown sugar and bourbon to browned butter. Cook until bourbon is reduced by half – 3 to 4 minutes.
- Remove from the heat and allow to cool a few minutes. Then add to the cream cheese, vanilla, black pepper, and salt.
- Whisk ingredients together, adding powdered sugar until smooth. Set aside until ready to top rolls.
Preparing Cooked Rolls
- Remove rolls from the oven and set aside for 15 to 20 minutes to slightly cool. Then drizzle with Brown Sugar Bourbon Icing to desired thickness.
- Sprinkle with Candied Pecans and Fennel Seeds and serve cinnamon rolls lightly warm or at room temperature. Serve extra Brown Sugar Bourbon Icing on the side.