Preheat oven to 400°F (200°C) and line a large rimmed baking sheet with parchment paper. Toss cubed butternut squash with olive oil, salt, pepper, and fresh thyme. Spread into an even single layer with space between cubes.

Roast for 22 to 25 minutes, tossing halfway through, until fork-tender and beautifully caramelized with blistered golden edges. Remove from the oven and let rest warm.

Place chopped kale in a large mixing bowl. Drizzle with 1 tablespoon olive oil and a pinch of salt. Using clean hands, vigorously massage the leaves for 2 to 3 minutes until dark green, silky tender, and reduced in volume by about one-third.

In a small saucepan over low heat (or in a mason jar in the microwave for 25 seconds), whisk together olive oil, apple cider vinegar, pure maple syrup, Dijon mustard, minced garlic, salt, and pepper until warm and emulsified.

Pour half the warm vinaigrette over the massaged kale and toss to coat evenly. Arrange the warm roasted butternut squash, sliced Honeycrisp apples, candied pecans, and dried cranberries over the greens.

Gently crumble the fresh goat cheese across the top, drizzle with the remaining warm maple cider dressing, and finish with a crack of black pepper. Serve warm or at room temperature!