Stuffed Acorn Squash

by Mark Ladner, Executive Chef Del Posto



Serves 6 people

For the squash:

9 small acorn squash


For the filling:

1 (28 ounce) can pureed Italian plum tomatoes

1 (250 gram) bag Taralli Savory Cookies

2 tablespoons unsalted butter

4 links sweet Italian sausage

4 links hot Italian sausage

1 package young kale, pre-washed

Extra-virgin olive oil, as needed

1 large red onion, cut into ¼ inch dice

1 bulb fennel, cut into¼ inch dice

1 large zucchini, cored and cut into¼ inch dice

1 clove elephant garlic, minced

Salt, to taste

Sugar, to taste

Pepper, to taste

Chili flake, to taste

Parmigiano-Reggiano cut into nice sized chunk

Breadcrumbs, as needed


For the squash:

Pre-heat the oven to 350 degrees F.


Cut each acorn squash in half lengthwise. Scoop out seeds, and roast cut-side down in an oven safe baking dish until fork tender. Stab the flesh of each squash no fewer than 25 times to release the interior heat, and let cool.


Leave the oven on.


For the filling: 

In a small covered sauce pot, over medium heat, reduce the tomato puree by half. Set aside.


Smash the cookies into bits inside their bag using a blunt object; a rolling pin or full bottle of wine will do nicely. You may want to wrap the bag in a kitchen towel before smashing. In a medium sauté pan, over medium-high heat, melt the butter, and add the smashed cookies. Sauté the cookies until they are nicely browned, about five minutes. Set aside.


Remove the meat from the sausage casings, and sauté over medium-high heat in a large sauté pan with two tablespoons of olive oil until nicely browned. Transfer the cooked sausage to a large bowl, and let cool until you can break apart the sausage chucks into pieces with your (impossibly) clean hands. Next, roughly chop the kale, using a mezzaluna if possible (so it feels Italian) and add the chopped kale to the sausage.


In sauté pan, over medium-high heat, heat two tablespoons of extra-virgin olive oil. Add the diced onion and cook for five minutes. Add the fennel, and additional olive oil if needed, and cook for five minutes more. Add the zucchini, two more tablespoons of olive oil, and cook for another five minutes. Finally, add the minced elephant garlic, season generously with salt, sugar, pepper, and chili flake. Add the cooked vegetable to the sausage and kale.


Combine the tomato reduction with the sausage and vegetables, and tumble contents of the bowl well. Adjust seasoning, set aside.


Grate the entirety of the Parmigiano-Reggiano and set aside.


Over-stuff the perforated squashes with tumbled veggie sausage mixture, and sprinkle with breadcrumbs and grated Parmigiano. Allow juices to settle into riddled squashes, and bake in the already pre-heated oven again until the cheese and breadcrumbs are nicely browned.


Serve immediately.

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