Apple pie filling and bourbon soaked cranberries are sandwiched in between layers of rich bread dough in this apple pull apart bread.
Before you begin to peel and slice the apples, set the cranberries in the bourbon to soak.
Heat a large pot over medium heat. Add the butter and let it melt. Once it's melted, add the apples, brown sugar, salt, cinnamon, and allspice. Bring the apples to a simmer, then cover the pot, lower the heat to low and let the mixture simmer until the apples are soft and have released their juices, about 10-12 minutes.
Using a slotted spoon scoop out the apples into a bowl. (Alternately use a colander set over the bowl and pour everything into the colander. Then return the juices to the pot.) Drain the cranberries, set them aside, and add the bourbon and apple cider to the pot. Bring to a rolling boil and cook until reduced to 1/4 - 1/3 cup, 6-8 minutes.
Combine the apples, reduced juices, and cranberries in the bowl and set it aside to cool. This takes about 1 hour at which time your dough will be ready too.
In the bowl of a standing mixer, whisk together the warm milk and the sugar by hand. Add the eggs and whisk to combine. Attach the dough hook and add the flour, salt, and yeast. Mix on low for 2 minutes to incorporate the flour and then increase the speed to medium for 1 minute.
With the mixer on medium, add the butter, one tablespoon at a time. Allow each addition to mix in before adding the next, about 30 seconds each time. Once you've added all the butter, continue kneading the dough for 5-6 minutes, until the dough looks soft and smooth.
Grease the bowl of the mixer and the dough with a little butter, cover the bowl with plastic wrap, and set it in a warm corner of the kitchen to let it rise. When the dough has doubled, 1 - 1 1/2 hours later, it is time to punch down the dough and go to the next step.
Get out a 9x5 inch loaf pan and cut off a piece of parchment paper large enough to fill the pan with some overhanging on the sides. Grease the pan so the paper will stick in place and then grease the paper. This bread is sticky!
Set your risen dough on a board and roll it out into a rectangle 12x15 inches in size. Slice the dough into 6 strips, each 3x12 and each strip into 4 squares. Spread out the cooled filling on the dough, leaving two squares alone. Those squares will fill in at the end of the bread.
Begin transferring the apple covered squares of dough into the prepared pan. Place the first two so that the dough side is against the end of the pan. And then add the rest in the same direction. This way you will have equal amounts of dough and apple filling all along the bread. Take the last two squares and slip them into the other end. You will need to scoop up fallen filling as you go and press the squares up against the end of the pan. Once you are done, you can smooth things out a little bit and make sure it is as even as you want it to be. (Remember: rustic.)
Cover the bread with plastic wrap and set it that corner of the kitchen to rise for 1 hour. At the half hour mark, preheat the oven to 350F.
Remove the plastic wrap and bake the bread for 30 minutes. Then cover the top of the bread with aluminum foil and continue baking for 25-35 minutes. Check the center of the bread. Once it reaches 190F, or a skewer comes out clean, take the bread out.
Let the bread rest for 10 minutes, then carefully pull it out of the pan and onto a cooling rack.
While the apple bread is cooling, boil the cider. In a medium saucepan, boil the cider down to 2-3 tablespoons. This will take about 12 minutes. Set it aside to cool completely.
Spoon the glaze over the cooled apple bread and serve.