Preheat the oven to 400 degrees F. Line 2 sheet pans with parchment paper.
Arrange the tomatoes in a single layer on the prepared sheet pan. Drizzle with 1 tablespoon olive oil and sprinkle with salt and pepper. Roast for 25-30 minutes until they are wrinkled the edges and are somewhat dried but still juicy in the center. (The tomatoes can be made up to 2 weeks in advance. Store in the refrigerator.)
Drizzle the bread with the remaining olive oil. Spread the the pesto on the bread Arrange the tomatoes on top and sprinkle with the chives and Parmesan before serving.