Heat the oil a large pan over medium-high heat, and add the shallots. Cook for about 5 minutes, until the shallots begins to turn brown.
Add the garlic and mushrooms and cook for 5-10 more minutes, until the mushrooms begin to turn brown and fragrant.
Add the kale to the pan and cook for about 3 more minutes, until it begins to wilt and turn bright green. Stir in the salt and pepper.
Add the red wine to the pan. Allow the vegetables to continue to cook until the wine evaporates, about 3 more minutes.
While the shallots and mushrooms are cooking, steam the squash using a steam insert in a large pot or an electric steamer. Steam for about 10 minutes, until the pieces are fork tender.
While the vegetables are cooking, bring the balsamic vinegar to a boil in small pot. Reduce heat to a simmer, and continue cooking for about 15 minutes. It should reduce down to about ¼ cup.
Heat the oven to 350° and line a baking sheet with parchment paper.
Unroll both cans of crescent roll dough and separate the dough into 8 rectangles. (4 per can.) Arrange the dough rectangles in ring so that the short sides of the dough rectangles form a 5-inch circle in center. The dough pieces should overlap.
Place the squash, and mushroom mixture into the dough, close to the center. The vegetables should cover about ⅓ to ½ of the dough.
Carefully bring the outer edge of each dough rectangle up over filling, tucking it under bottom layer of dough to secure it. Repeat this around ring until you’ve wrapped all of the filling in the dough. Some of the filling will show. Gently separate the some of dough perforations on top of the ring until a little filling peeks through.
Brush the dough with the balsamic glaze. If you have any left, you can drizzle it over the ring when you serve it.
Bake for 25-30 minutes, or until the dough is golden brown. Let cool for 10 minutes before slicing.