Preheat your oven to 425°F (220°C) and line a sheet pan with parchment paper for easy cleanup.
Rub the chicken thighs with a tablespoon of olive oil, salt, pepper, sage, and cinnamon, making sure they’re well coated on all sides.
Arrange the seasoned chicken on one side of the prepared sheet pan, skin side up for crispy skin.
Slice the apples into wedges, then scatter them around the chicken, along with cubed squash.
Sprinkle the minced garlic over the vegetables and drizzle everything with the remaining tablespoon of olive oil.
Transfer the sheet pan to the oven and roast for about 40 minutes, or until the chicken skin is crisp and the vegetables are caramelized and tender.
Once done, remove the pan from the oven, and let the chicken rest for a few minutes before serving to allow the juices to settle.
Serve the crispy chicken thighs with the sweet roasted apples and squash for a cozy, fall-inspired meal.