Preheat the oven to 400℉. Line two baking sheets with parchment paper.

In a medium bowl, stir together cubed butternut and acorn squash, 2 Tbsp olive oil, 3 Tbsp maple syrup, and 1 tsp cinnamon. Place on a large sheet pan. Roast the butternut squash and Acorn Squash for 25 minutes or until softened, turning once half-way through baking.

Once the squash is fork tender, sprinkle with pecans and 2 Tbsp maple syrup and return to the oven for an additional 5 minutes.

While squash is baking, stir together Brussels sprouts, 2 Tbsp olive oil, salt (to taste), and toss to combine. Place on another baking sheet, flat-side down. Roast Brussels sprouts for 15 minutes. Remove from oven, flip Brussels over and drizzle with 2 Tbsp maple syrup. Return to oven for 10 minutes or until golden brown and tender.

Allow squash and Brussels to cool for a few minutes. Toss the roasted butternut squash, roasted acorn squash, and roasted Brussels sprouts, dried cranberries, and pepitas together. Finish with an extra drizzle of 2 Tbsp maple syrup, feta, and thyme.