Wholesome Cinnamon Rolls with Naturally Sweet Date Filling

Few things compare to the aroma of freshly baked cinnamon rolls wafting through the kitchen. These Whole Wheat Cinnamon Rolls Made with Dates take a classic favorite and give it a wholesome twist—using whole wheat flour, natural date sweetness, and a slow-rise overnight fermentation for enhanced flavor.

This recipe uses rapadura sugar, a minimally processed sweetener that retains its natural minerals, and dates as the primary source of sweetness for the filling. The result? A treat that is not only delicious but also rich in nutrients and fiber. If you're ready to make a batch of soft, naturally sweetened cinnamon rolls, let's get started!

Whole Wheat Cinnamon Rolls with Dates & Warm Spices

Ingredients (Makes 12 Rolls)

For the Dough:

• ½ cup milk

• ¾ cup water

• ½ cup rapadura sugar

• ½ tsp salt

• 4 tbsp butter

• 3¾ cup (465g) whole wheat flour

• 2 room temperature eggs

• 1 tsp vanilla extract

• 2¼ tsp instant yeast

For the Filling:

• 4 tbsp melted butter

• ½ cup whole pitted dates (or ¼ cup date syrup)

• ¼ cup rapadura sugar

• 1 tbsp cinnamon

• ¼ tsp nutmeg

• ¼ tsp cardamom

• Pinch of salt

For the Glaze:

• ½ cup (60g) organic powdered coconut milk

• 2–3 tbsp warm almond milk (as needed to thin)

• ⅛ tsp vanilla extract

  
  

Instructions

Step 1: Prepare the Dough

1. In a medium saucepan, combine milk (dairy or non-dairy), water, rapadura sugar, salt, and butter.

2. If using dairy milk: Heat over medium-high heat until the milk is scalded (just before boiling) and the butter and sugar fully melt. Scalding helps improve gluten formation by denaturing whey proteins.

3. If using non-dairy milk (e.g., soy milk), heat until warm (around 110°F)—no need to scald. This helps dissolve the sugar and butter while maintaining an ideal temperature for yeast activation.

4. Remove from heat and allow the mixture to cool below 110°F before proceeding. This step is crucial, as liquids that are too hot can kill the yeast.

   

   
   

5. Once cooled, pour the mixture into the bowl of a KitchenAid stand mixer.

6. Add whole wheat flour and mix on low until mostly combined.

7. Add eggs and vanilla extract. Mix until a cohesive dough forms. It may look slightly separated at first, but keep mixing until smooth.

8. Let the dough rest for 15 minutes to allow the flour to absorb moisture.

Step 2: Make the Filling

While the dough is resting, prepare the filling:

1. Melt butter in a small saucepan.

2. If using whole dates, blend them into a paste using a food processor with a splash of warm water. Alternatively, use date syrup for easier mixing.

3. If using rapadura sugar, break it down by grating or grinding it into fine granules—it starts as a hard brick but dissolves better when finely processed.

4. Mix melted butter, date paste or syrup, rapadura sugar, cinnamon, nutmeg, cardamom, and salt until the mixture resembles a sticky paste.

Step 3: Activate the Yeast & Knead the Dough

1. After the dough has rested, add the yeast and mix until well incorporated.

2. Increase the mixer speed to level 2 and knead for 8–10 minutes, or until the dough passes the windowpane test (stretching the dough thin without tearing).

3. Cover and let rise in a warm place for 1–2 hours or until doubled in size.

Step 4: Shape the Cinnamon Rolls

1. Once the dough has risen, transfer it to a lightly oiled surface.

2. Roll it out into a 15x17-inch rectangle using a rolling pin.

3. Evenly spread the cinnamon-date filling over the dough, breaking it apart with your hands if needed.

4. Starting from the short side, roll the dough into a tight log.

5. Cut into 12 equal pieces using a sharp knife or dental floss for clean slices.

Step 5: Second Rise (Overnight Refrigeration Option)

1. Place the rolls in a parchment-lined 9×13-inch baking dish.

2. Cover and let rise for 40 minutes at room temperature, or refrigerate overnight for deeper flavor.

If refrigerating overnight:

• In the morning, set the rolls on the counter for 1–2 hours before baking to allow them to reach room temperature.

  

  
  

Step 6: Bake the Cinnamon Rolls

1. Preheat oven to 350°F (175°C).

2. Bake for 18–20 minutes or until golden brown and cooked through.

Step 7: Make the Glaze & Serve

1. In a small bowl, whisk together organic powdered coconut milk, warm almond milk, and vanilla extract until smooth.

2. Drizzle over warm cinnamon rolls before serving.

Helpful Tips & Techniques

How to Work with Rapadura Sugar

Breaking It Down for Easier Use

• Grate it: Use a fine cheese grater or microplane to create small, easily dissolvable granules.

• Blend or process it: A food processor or spice grinder can turn rapadura into a fine powder for smoother mixing.

• Crush it manually: If you don't have a grinder, place it in a Ziplock bag and crush it with a rolling pin.

• Since rapadura sugar doesn't dissolve as quickly as refined sugar, always mix it into warm or hot liquids to help break it down.

What's the Benefit of an Overnight Rise?

Yeast is the key leavening agent in these cinnamon rolls, responsible for their light, airy texture. As the yeast consumes natural sugars from the dough, it undergoes fermentation, producing carbon dioxide gas. This gas gets trapped within the gluten network, causing the dough to expand and rise.

The overnight refrigeration method slows down this fermentation process, allowing for:

• Enhanced flavor development – A more complex, slightly tangy depth to the dough.

• Better texture – A softer, more structured cinnamon roll with improved gluten formation.

• Easier baking in the morning – just bring to room temp and bake!

These Whole Wheat Cinnamon Rolls Made with Dates are the perfect balance of wholesome and indulgent. By swapping processed sugars for rapadura and dates, this recipe provides deep caramel-like sweetness while keeping things naturally nourishing. These cinnamon rolls have all the indulgence of the ones found in the mall but with ingredients you can feel good about!

Have you tried making naturally sweetened cinnamon rolls before? Share your experience in the comments!