Preheat oven to 400℉.
Place the seeded spaghetti squash, cut side up, on a baking sheet, and rub with oil.
Bake until tender and just beginning to brown on the edges, about 40 minutes.
Reduce oven temperature to 350℉.
Place tomatoes on the baking sheet. Drizzle with olive oil and season with salt and pepper.
Bake tomatoes until they begin to shrivel and become juicy.
If using home-made pesto, while spaghetti squash and tomatoes are baking, make the pesto (see below).
Once the spaghetti squash has baked, allow it to cool slightly. If liquid has collected in the center, drain off, then scrape out the insides with a fork, and separate into spaghetti strands, and place in a large bowl. In the bowl, add the pesto, and toss until combined.
Top with the roasted tomatoes, and more Parmesan cheese, salt and pepper to taste.