Preheat your oven to 400°F (200°C).
Rinse cherry tomatoes under cold water and pat dry. Place in a large mixing bowl.
Slice off the top of the head of garlic to expose the cloves.
Drizzle 2 tablespoons of olive oil over the tomatoes, add salt, pepper, and red pepper flakes. Toss gently.
Line a baking sheet with parchment paper. Spread tomatoes in a single layer and place garlic cut side up. Drizzle with olive oil and sprinkle with salt. Roast for 25-30 minutes.
Bring a large pot of salted water to a boil. Add pasta and cook according to package instructions until al dente.
Squeeze roasted garlic into a large mixing bowl, add tomatoes and juices, mash together, then add olive oil, balsamic vinegar, salt, and pepper.