Dates are nature’s sweet, sticky treat—perfect for baking but equally delightful in salads, appetizers and more. One of my favorite small bites is a simple bacon-wrapped date stuffed with a pecan; salty, sweet and crunchy. Inspired by that same contrast of flavors, I developed these Date, Walnut and Bourbon Cinnamon Rolls finished with a boozy cream cheese icing. The combination of caramel-like dates, toasted walnuts and a splash of bourbon gives the filling an irresistible depth.
While pre-chopped date pieces from the baking aisle are convenient, whole Medjool dates are far superior in texture and flavor. If you use whole dates, remove the pits by slicing the fruit and pulling the seed out before processing or chopping. The difference is worth a few extra seconds of prep.
The idea for these rolls came after a cinnamon roll run to a local bakery—one taste and I wanted to recreate something similar with dates and nuts. I added bourbon to both the filling and the cream cheese icing, which elevates the flavors and gives the rolls an adult-friendly finish. The dough is a straightforward enriched roll dough, and the filling is essentially a supersized cinnamon-sugar mixture studded with dates, toasted walnuts and a touch of bourbon.
The original cinnamon roll dough recipe I used came from a neighbor; it yields soft, pliable dough that bakes up tender and rich. One note from my first batch: I used a baking dish that was slightly too large, which caused the rolls to spread rather than rise tall. For best results use a 9×13-inch pan so the rolls have room to puff up and stay nicely rounded.
Yes, I used bourbon. A little in the filling and a little in the cream cheese icing makes a noticeable difference—warm, boozy notes pair wonderfully with dates and walnuts. The cream cheese icing is silky and just sweet enough; you can add a teaspoon of bourbon if you like a pronounced boozy flavor.
I like these best warm from the oven. If you need to hold them briefly, cover them to keep them soft—dry climates will dry them out quickly. Reheat gently in the oven or microwave if serving later. The end result is beautifully sticky, cinnamon-forward rolls with rich pockets of date and walnut and a finishing tang from the bourbon cream cheese icing.
Date, Walnut and Bourbon Cinnamon Rolls with Cream Cheese Frosting
Creative Culinary
1 hr
30 mins
1 hr 30 mins
Ingredients
For the Dough:
- ¼ ounce dry yeast
- ¼ Cup + 1/2 teaspoon sugar
- ¼ cup water
- ½ cup milk (room temp)
- 2 tablespoons brown sugar
- 1 egg
- 1 egg yolk
- ½ teaspoon vanilla
- 1 teaspoon salt
- 8 tablespoons unsalted butter (soft)
- 3 cups all-purpose flour
For the Date Filling:
- ½ cup sugar
- ½ cup brown sugar
- 1 cup dates
- ½ cup toasted walnuts (toast first for better flavor)
- 1 tablespoon cinnamon
- ½ teaspoon salt
- 2 Tbsps bourbon
- 4 tablespoons unsalted butter (melted)
For the Cream Cheese Icing:
- 3 oz softened cream cheese
- 1 Tbsp softened butter
- 1½ cups powdered sugar
- 2 Tbsp milk
- 1 tsp bourbon (optional)
- Finely ground walnuts for garnish (optional)
Instructions
To Make the Dough:
- Put yeast, 1/2 teaspoon sugar and water into a mixing bowl. Let sit 10 minutes until foamy.
- Stir in milk, brown sugar, sugar, eggs, vanilla and salt until combined.
- Add flour one cup at a time.
- Mix with a dough hook 4–5 minutes until soft and combined.
- Add softened butter and beat into the dough; the dough will be pliable and slightly sticky—avoid adding extra flour.
- Beat with the dough hook another 4–5 minutes.
- Lightly flour a counter, turn out the dough and dust the surface of the dough with flour.
- Place dough in a clean bowl, cover and let rise about two hours until doubled (a warmed oven at roughly 90–95°F speeds this to about 90 minutes).
To Make the Filling:
- Cut dates in half and remove pits.
- In a food processor combine sugar, brown sugar, dates, toasted walnuts, cinnamon, salt and bourbon. Pulse until combined but still slightly chunky.
- Cut cold butter into chunks, add to the processor and pulse until just combined.
To Assemble Cinnamon Rolls:
- Roll the dough on a floured surface into a rectangle about 12″ x 24″.
- Spread the date filling evenly over the dough.
- Starting at the short end, roll the dough tightly into a cylinder roughly 12–14″ long.
- Cut the roll into 8 even pieces, place each cut-side up in a buttered 9×13″ baking dish.
- Cover and let rise 1 hour.
- Preheat oven to 375°F about 15 minutes before rising is complete.
- Bake 15 minutes, rotate the pan, then bake another 10–15 minutes until lightly browned.
- Let rolls cool 20 minutes before icing.
To Make the Icing:
- Cream together the softened cream cheese and butter.
- Add powdered sugar ½ cup at a time until incorporated.
- Blend in bourbon and enough milk to reach a smooth, pourable consistency.
- Drizzle the icing over warm rolls and garnish with finely ground walnuts if desired.
Notes
I sometimes prepare these the night before. After cutting the rolls and placing them in the baking dish, cover and refrigerate. In the morning, warm the oven briefly to about 90°F, turn it off and let the rolls proof in the warm oven for an hour before baking. Another method is to proof the pieces first, then cover and refrigerate overnight; they’ll be ready to bake first thing in the morning. Serve warm; reheat in the oven or microwave if not serving immediately.
Tried this recipe?
Let us know how it was!