Caramel Apple Milkshake

Before getting started, use a small paring knife to peel and slice 2 large apples into about 16 slices each. Then place your milkshake glasses in the freezer so that they're nice and cold for the apple milkshake.
Start by adding the sliced apples, brown sugar, cinnamon and water to a medium saucepan over medium-low heat on the stovetop.
Cook the apples down 'til softened, about 10 minutes. Stir often to avoid scorching the pan.
Use a large colander to drain the water out of the apples, and then let them cool for about 15 minutes before moving on to the next step.
Once the apples are cool, add the milk, ice cream, and cooked apples to your blender.
Blend until everything is broken down and smooth, about 30 seconds on high speed.*
When it has reached the desired consistency, pour your apple shake into your cold milkshake glasses. Top it off with a big dollop of homemade whipped cream, and drizzle on a little caramel sauce. Yum!