Slice and cut the bread into 1-inch cubes. You should have around 12 cups of cubed bread—a little more or less is fine. For best results, let the bread cubes sit uncovered at room temperature for a few hours (or up to 1 day) to dry out. If you don’t have the time for that, spread the chunks of bread on a lined baking sheet and toast in a 300°F (149°C) oven for 10 minutes.
Grease a 9×13-inch or any 3–4-quart oven-safe dish with nonstick spray. Spread half of the bread cubes into the prepared baking pan.
Using a handheld or stand mixer fitted with a whisk attachment, beat the room-temperature cream cheese on medium-high speed until completely smooth. Beat in the confectioners’ sugar and ¼ teaspoon vanilla extract until combined. Drop random spoonfuls of cream cheese mixture on top of the bread. Top with most of the berries (reserve a few berries for the top, for looks) and then the remaining bread cubes. Place any reserved berries on top. Set aside.
Whisk the eggs, milk, cinnamon, brown sugar, and remaining vanilla extract together until combined. Pour evenly over the bread. Cover the pan tightly with plastic wrap and refrigerate for at least 3–4 hours and up to 24 hours. Overnight is best.
Preheat oven to 350°F (177°C). Remove pan from the refrigerator.
Bake uncovered for 45–55 minutes or until golden brown on top. Dust with confectioners’ sugar, top with strawberry topping, and/or drizzle with maple syrup. Serve warm.
Cover leftovers tightly and store in the refrigerator for 2–3 days.
