Scoop cream cheese spread into frosting bag (fitted with small round tip). Place the round tip into the hole of the pitted date and squeeze cream cheese into date. Repeat process with all the dates.
Take a small strip of bacon and wrap it around each date, securing it with a toothpick through the center.
Lightly sprinkle all sides of the dates with brown sugar and place on a foil lined baking sheet. Drizzle with maple syrup and bake for 10 minutes. Flip each date over and bake for an additional 10 minutes, until bacon is browned and crispy.