Heat a large skillet to medium-high on the stove top. Once hot, add the bacon and cook, flipping every 1 to 2 minutes, until fat has seeped out and bacon has reached desired amount of crisp, about 3 to 5 minutes. Remove bacon from skillet and transfer to a cutting board, leaving the bacon drippings in the skillet. Chop the bacon and set aside until ready to use.

Add the chopped Brussels sprouts to the skillet with the bacon drippings and reduce the heat to medium. Stir the Brussels sprouts well, cover, and cook for 2 to 3 minutes. Uncover, stir, and continue cooking until Brussels sprouts have reached desired done-ness, about another 4 to 5 minutes. Transfer Brussels sprouts to a plate and set aside.

Place the skillet back on the hot stove top and add 1 to 2 tablespoons of olive oil if necessary. Transfer the chopped acorn squash to the skillet, stir well, and cover. Cook 4 to 5 minutes, stir, and remove the cover. Cook an additional 8 to 10 minutes, until acorn squash is golden-brown and cooked through.

Transfer the Brussels sprouts to the skillet with the acorn squash, along with the chopped bacon, cinnamon, sea salt, pure maple syrup, and pecans. Stir well to combine and continue cooking until heated through, about 3 minutes.

Transfer to a serving bowl and serve alongside your favorite entree.