Make the whipped cream cheese filling: Add the cream cheese, heavy cream, and honey in a bowl. Using an electric mixer, beat on high speed until light and fluffy. Gently fold in the strawberries until just combined.
Make the custard: In large a pan (I used a large pyrex pan that fits 6 slices of bread), whisk the eggs, milk, honey, cinnamon, vanilla, and salt until well combined.
Cut the challah loaf into 1 1/2 inch slices (about 6 slices total). Carefully, cut pockets on the top edge of each slice for the filling. Stuff in the cream cheese mixture to your liking, being careful not to overstuff it. You don't want it to break apart. Repeat with the remaining slices.
Soak the prepared challah bread slices in the custard mixture for about 5 minutes, turning halfway through. If not enough room in the pan for all the slices, transfer some of custard mixture and bread slices into another pan.
Heat about 1-2 tablespoons of butter in a griddle over medium heat. Cook each slice for about 3 minutes per side, or until golden brown.
Serve warm with maple syrup, fresh berries, and dust with confectioners sugar.