Preheat oven to 400 Fahrenheit. Line the baking sheet with parchment paper.
Cut the squash in 2 halves, scrape out the seeds and the fiber out of each half. Repeat with a second squash.
Drizzle olive oil over the cut sides and inside of the squash. Generously season with salt and pepper.
Place the 4 squash halves on the prepared baking sheet cut side down.
Bake for about 30 or 40 minutes on the middle rack. Remove it from the oven when it's cooked through and soft.
Make the stuffing while the spaghetti squash is roasted in the oven. Heat 1 tablespoon of olive oil on medium heat in a large, high-sided skillet.
Add crumbled sausage and sliced mushrooms and cook on medium heat for about 5 minutes or until the sausage is cooked.
Add minced garlic, Italian seasoning, red pepper flakes, and chopped tomatoes (reserving some for later use).
Add fresh spinach in batches to the sausage mixture and cook until the spinach wilts.
Remove the spaghetti squash from the oven and turn cooked squash halves cut sides up.
Let it cool slightly. Divide the Italian sausage mixture among the 4 halves and stuff the squash until the mixture is leveled.
Top with the remaining sliced cherry tomatoes and the shredded Parmesan cheese.
Return stuffed spaghetti squash to the preheated oven and roast at 400 F for 15 more minutes until the cheese mixture melts.
When serving, top with fresh thyme.
