Roast the Squash and Sweet Potato

Preheat the oven to 400 degrees. Cut the acorn squash in half and scoop the seeds into a bowl — set them aside. Cut each half into slices about 3/4 inch thick. No peeling required; the skin is perfectly fine to roast on and the flesh pulls away from it easily once golden brown. Place the squash slices in a single layer on a large baking sheet. Brush both sides with olive oil and season with salt and black pepper.

Wash the sweet potato and cut into small chunks, roughly the same size so they cook evenly. Add them to the large baking sheet with the squash. Drizzle with a little olive oil and toss to coat.

Roast for 20 to 25 minutes, turning once halfway through, until the squash is tender and golden brown at the edges and the sweet potato is cooked through. Remove from the oven and let everything cool for a few minutes before assembling. Placing very hot vegetables straight onto baby kale will wilt it more than you want.

Toast the Squash Seeds

Rinse the squash seeds and pull away as much of the stringy pulp as you can. Pat them dry, then spread in a single layer on a separate small sheet pan. Drizzle with a teaspoon of olive oil and season with salt. Roast at 400 degrees for 10 to 15 minutes, stirring once or twice, until golden brown and crisp. The seeds near the edges of the pan go quickly, so keep an eye on them. If you would rather skip this step, toasted pumpkin seeds, sunflower seeds, or slivered almonds are a great substitute.

Assemble the Salad

Add the baby kale to a large bowl or large serving bowl. Layer the roasted squash slices and sweet potato over the greens in a casual pile. Scatter the shallot, dried cranberries, cheese, and seeds over the top. Drizzle generously with the maple Dijon vinaigrette, or your balsamic reduction just before serving.