Place milk and dates in a large pot and bring to a boil over medium-high heat. (Watch the milk carefully, so it does not boil over.) Remove from heat and allow to cool slightly, about 5 minutes.
48 fl oz (6 cups) whole milk
⅔ cup medjool dates, pitted
Working in batches to best fit your blender, transfer cooled date-milk to the blender. Add cocoa powder, vanilla, cinnamon, and salt; blend on high until very smooth, about 2 minutes.
¼ cup cocoa powder
½ tsp vanilla extract
¼ tsp cinnamon, ground
⅛ tsp salt
Return hot chocolate mixture to the pot and reheat over medium-high heat to preferred temperature.
To serve, divide hot chocolate between mugs and enjoy!