Making ravioli from scratch is so much fun because you can fill it with whatever you want! This squash and herb ravioli is certainly among my favorites. A simple sauce of orange juice and brown sugar complements the sweetness of the squash filling perfectly. For a more deluxe treat, try making a shallot and sage cream sauce instead. Although it is not required for this recipe, you may want to consider purchasing a ravioli cutter because they really help make your ravioli the right size and evenly shaped. Ravioli do take some extra effort to make but you can spend a weekend day making several batches and then freeze some for an easy weeknight meal later on.
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Winter Squash Ravioli
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Warm, Whole-Grain Bread

Ingredients

for the filling...
1 butternut squash (about 1-1/2 pounds)
2 tablespoons olive oil
salt and pepper
1 clove of garlic, minced
about 5 sage leaves, minced
pinch of nutmeg
2 to 3 tablespoons grated pecorino-romano cheese
1 tablespoon chopped fresh parsley

for the ravioli dough...
2 cups unbleached all-purpose flour
1/2 teaspoon salt
3 large eggs
1 tablespoon olive oil

for the sauce...
3/4 cup freshly squeezed orange juice
2 tablespoons brown sugar
1 tablespoon balsamic vinegar
2 tablespoons butter
1/4 cup toasted hazelnuts, coarsely chopped

Cooking Instructions

Preheat the oven to 375 degrees. Cut the squash in half lengthwise, scoop out the seeds, and brush the entire surface with about 1 tablespoon of olive oil. Season with salt and pepper and bake, cut side down, until completely soft (about 1 hour). When cool enough to handle, scoop the soft flesh out into a bowl, mash lightly with a fork and set aside.

Heat the remaining tablespoon of olive oil in a large skillet over medium heat. Add the garlic and sage and cook until warm and fragrant without letting the garlic brown. Add the butternut squash and cook, stirring frequently, until the squash has dried out some (about 10 minutes). Remove from heat and season with the nutmeg, cheese, parsley and salt and pepper to taste. Cool to room temperature before using in the ravioli.

Sift the flour and the salt together into a large mixing bowl and make a well or shallow pit in the center. In a separate bowl, whisk together the eggs and the olive oil. Pour the eggs into the well and start incorporating the flour into it with a fork. Once enough of the flour has been incorporated to keep the liquid from being too runny, transfer the contents from the bowl to a clean work surface or counter dusted with flour. Start kneading the mixture to finish blending it all together. Knead for another 5 to 10 minutes, dusting the counter with more flour, if necessary, as you go. At this point, the dough should be satiny and elastic in texture. Wrap the dough lightly in plastic wrap and let rest for 30 minutes to 1 hour at room temperature.

Using a pasta machine, follow the manufacturer's instructions and roll the pasta dough out to one of the thinnest settings. Cut the strips into lengths that are easy to handle (about 12 to 16 inches long), lightly dust each with flour, and set the strips on top of one another. Work with one strip at a time and keep the others covered with a kitchen towel. Dust the counter and sheet of dough with flour. Drop tablespoons of the filling onto the bottom half of the pasta sheet, about 2-inches apart. Fold the top half over the filling. With your fingers, gently press out air pockets around each mound of filling. Use a sharp knife to cut each mound into squares and crimp the edges of each with a fork to make a tight seal. Dust the ravioli and a sheet pan with flour to prevent the pasta from sticking and lay them out to dry slightly while assembling the rest.

To make the sauce, combine the orange juice, brown sugar, and balsamic vinegar in a small pot and simmer over medium heat until slightly reduced. Season with salt and pepper as needed. Melt the butter into the sauce and keep warm over low heat as you cook the ravioli.

Cook the ravioli in plenty of boiling salted water for 3 to 4 minutes (they'll float to the top when ready). Lift the ravioli from the water with a large strainer or slotted spoon. In a large warm bowl, gently toss the ravioli with the orange sauce and serve garnished with the chopped hazelnuts and minced parsley.

Makes 4 to 6 servings

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Always use plenty of flour when working with the pasta dough, especially once the ravioli have been cut. They have a real tendency to stick together. You can always shake off additional flour before cooking the ravioli and any flour that you don't shake off will come off in the water during cooking.

To make life easier, buy yourself a ravioli cutter. You can find them in any kitchen store and there are several different kinds to choose from, from square or round to single or multiple. They're great for making perfectly shaped ravioli, although there is certainly something to be said for rustic, hand-cut ravioli as well.

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