Delicata Squash with Caramelized Shallots
1 Red Dog delicata squash
2 Tbsp. olive oil
1/4 cup dry sherry (such as fino)
Kosher salt and freshly ground black pepper
1 Tbs. unsalted butter
1 cup thinly sliced Red Dog shallots (2 to 3 large)
4 tsp. finely chopped fresh sage
Heat the oven to 350°F. Trim the ends of the squash, cut in half lengthwise and scoop out the seeds. (No need to peel it—the skin is tender enough to eat.) Slice the halves crosswise 1/2 inch thick.
Heat 1 Tbsp. of the oil in a 10-inch skillet over medium-high heat. Add half of the squash in a single layer and cook without moving until the slices begin to brown, about 2 minutes. Flip and cook until the second side begins to brown, 1 to 2 minutes. Transfer to a 9×13-inch baking dish. Repeat with the remaining squash. Arrange the squash in a single layer in the dish. Sprinkle with 2 Tbs. of the sherry, 1/2 tsp. salt, and a few grinds of pepper.
Heat the remaining 1 Tbs. olive oil and the butter in the skillet over medium heat. Add the shallots and a pinch of salt and cook, stirring frequently, until the shallots turn deep golden brown on the edges, 3 to 5 minutes. Take the pan off the heat and immediately add the sage and the remaining 2 Tbsp. sherry, scraping up the browned bits on the bottom of pan. Scatter the shallots over the squash.
Cover the pan with foil and bake until the squash is tender when pierced with a fork, 25 to 30 minutes. Season to taste with salt and pepper.