Place squash halves, cut sides down, on a foil-lined baking sheet coated with cooking spray. Bake at 400° for 30 minutes or until tender. Cool. Scoop out pulp; discard peel. Mash pulp. Combine oregano, squash pulp, and butter in a large bowl. Stir in 2 ounces (about 1/2 cup) cheese, 1/4 teaspoon salt, and 1/4 teaspoon pepper. Working with 1 wonton wrapper at a time (cover remaining wrappers with a damp towel to keep them from drying), spoon about 1 1/2 teaspoons squash mixture into center of each wrapper. Moisten edges of wrapper with beaten egg; bring 2 opposite corners together. Pinch edges together to seal, forming a triangle. Repeat procedure with remaining wrappers, squash mixture, and egg. Cover ravioli loosely with a towel to prevent drying.
Place garlic in a food processor, and pulse until finely chopped. Add remaining 1/2 ounce (about 2 tablespoons) cheese, remaining 1/8 teaspoon salt, remaining 1/4 teaspoon pepper, spinach, basil, and 2 tablespoons walnuts. With processor on, slowly pour oil, broth, and juice through food chute. Process until well blended. Place pesto in a large bowl.
Bring 6 quarts water to a boil in a large Dutch oven. Add half of ravioli; cook 3 minutes or until thoroughly cooked. Remove ravioli with a slotted spoon. Repeat procedure with remaining ravioli. Add ravioli to pesto; toss gently to coat. Arrange 6 ravioli on each of 6 plates; sprinkle each serving with 1 teaspoon walnuts.
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It could be that I've never made ravioli or worked with wonton wrappers or really even made fresh pasta before, but this recipe was a nightmare for me. Yes, the ravioli took about 2 hours to fill (I also used all 50 wrappers and still had leftover filling), but I love cooking so I was fine with that. But once filled, the ravioli stuck together. The ones I could separate stuck together when I put them in the pot. The ones of THOSE I could separate stuck together when I set them out to cool. Then, when I tried to "toss" them with the pesto, they stuck together AGAIN, and/or tore open. All in all, I had to throw about half of them away because they stuck and tore open at some point in the process. My boiling water ended up filled with mashed butternut squash. Not super appetizing.If I were to make it again (I won't), I would make a TON of room, maybe get like 5 cookie sheets and 3 assistants, and lay each ravioli out separate from the rest. I would probably only be able to boil 3-4 at a time, and then I would again lay them separated from the rest. Then, I would coat each individual one with pesto (which I'd probably add more olive oil to prevent sticking, though that's no longer cooking light), THEN put them on a plate or in a container to store. All-in-all, just not worth the effort, time, and space.The pesto tasted great, though. I'd probably make that again.
Albeit delicious, I agree with an earlier review, that this is not a weeknight meal. Unless you have another set or two of extra hands to help assemble the raviolis; this took about an hour alone. Definitely a weekend repeat though. Could always assemble and freeze, then it could easily be done on a weeknight.