Preheat your oven to 350 degrees and grease a 9”x13” deep baking dish or use a 12” deep oven safe skillet
Slice the loaf of bread into 1 inch cubes, spread the cubes over a large baking sheet and bake the bread for about 15 minutes to dry it out and then set the bread aside for now (leave the oven set to 350 degrees)
Add 2 tablespoons of butter into a large skillet placed over medium heat
Add the minced garlic, diced yellow onion and diced celery into the skillet and cook for about 5 minutes or until they have softened a bit
Season with a large pinch of salt and black pepper
Add 6 tablespoons of butter into the skillet and once the butter has melted, add 2 cups of broth and bring to simmer and transfer the skillet off of the heat
In a large bowl, whisk 1 1/2 cups of heavy cream with 2 large eggs
Add the dried bread cubes, chestnuts, herbs and another pinch of salt and black pepper into the bowl
Pour the broth mixture over the bread and gently mix until everything is evenly distributed
Transfer the dressing into the prepared dish and press any exposed chestnuts down a bit (they can get tough if exposed too much during the bake)
Bake in a 350 degree oven for about 40-45 minutes or until golden brown and set in the center.