Recipe: Squash Stuffed with Bread, Cheese, and Bacon

We have Dorie Greenspan to thank for this recipe. Last year, we wrote about her Pumpkin Filled with Bread and Cheese, a recipe we've since seen updated in Fine Cooking. Thing is, we'd rather eat squash than pumpkin—and we only needed to feed two people. So we swapped in some acorn squash and made a few changes (including an all-important step for getting that delicious, caramelized crust on top).
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Acorn squash was perfect for downsizing Dorie's recipe. With its nice bowl shape, the squash-to-filling ratio would be about right (as opposed to with a butternut squash, where you have a bowl at one end and then a long stem of squash flesh).

The problem was that Dorie put the cap back on her pumpkin after filling it with bread, cheese, and cream, so she had a little oven-within-an-oven to get everything cooked through. We were slicing a squash in half and leaving the stuffing exposed.

The first time we made this dish, we baked it for almost two hours, covered, before we finally figured out this trick: You need to bake the squash upside-down. Just like you would if you were roasting it. The heat gets trapped and the hard squash cooks much, much faster. The bonus? The filling, which is smashed down against the bottom of the dish, caramelizes on its surface to form a crunchy, brown crust—the perfect texture to go with the soft squash and gooey cheese.

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Acorn Squash Stuffed with Bread, Cheese, and Bacon adapted from Dorie Greenspan; serves two

2 slices bacon
1 small shallot, sliced thin
1 clove garlic, minced
2 teaspoons chopped sage (about 3 to 4 leaves)
1 1/2 cups of bread cubes (from a crusty loaf or baguette, cut into dice-sized pieces)
3/4 cup mixed grated cheeses (We used gruyere, fresh mozzarella, and cheddar. This would be a great time to use up little odds and ends.)
3 tablespoons heavy cream
1 medium acorn squash, sliced lengthwise and seeded*
olive oil
salt and pepper

Heat oven to 400 degrees.

Cook the bacon in a skillet over medium heat until crispy. Remove, crumble, and set aside. In the same pan, cook the shallot until beginning to brown, about 4 to 5 minutes. Add the garlic and sage and cook just until fragrant, about one minute (don't burn the garlic).

In a medium bowl, combine the shallot mixture, bread cubes, cheeses, and bacon. Pour in the cream and stir until everything is moistened. Add a pinch of salt and a few grinds of pepper.

Rub a drizzle of olive oil over the squash, coating the sliced edges and the cavity. Sprinkle over some salt and pepper. Divide the stuffing between the halves, packing it in so that the squash can still lie flat when turned upside-down.

Carefully place the squash halves upside-down in a baking dish. Bake for about one hour, until the flesh of the squash can be easily pierced with a knife. If the juices and cheeses start to burn after 30 or 45 minutes, add a few tablespoons of water to the dish. Once the squashes are cooked, use a spatula (or two) to flip them over. Serve as is or slice down the middle.

*The size of the seed pocket is different with each squash. Ours was quite small, so we scooped out a little extra flesh to make room for all of the stuffing.

Related: How to Eat Half a Squash for Dinner

(Images: Elizabeth Passarella)

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