Arrange the tomatoes and garlic in a large baking dish. Drizzle with olive oil and toss with oregano, basil, red pepper flakes, ½ teaspoon salt, and ½ teaspoon black pepper.
Bake at 400 degrees for about 30 minutes.
Meanwhile, cook the pasta to al dente according to package directions. Drain, reserving ½ cup of pasta water and set aside.
When tomatoes are finished, remove them from the oven and toss with the pasta, adding small amounts of the pasta water if needed, or a drizzle of olive oil. Top with fresh basil and fresh grated Parmesan cheese if desired.
Storage: Place leftover pasta in an airtight container and keep it in the fridge for 3-4 days.Freezing: Pasta can be hit or miss in the fridge. It can get a little mushy so proceed with caution. Place in an airtight container and freeze for 4-6 months.Reheating: If frozen, thaw completely first. Reheat on the stovetop or in the microwave.