Preheat oven to 350°.
Place the tomatoes, cut sides down, on a foil-lined baking sheet. Brush with 1 tablespoon oil; sprinkle with pepper. Bake at 350° for 50 minutes. Wrap shallots in foil; add to baking sheet. Bake an additional 40 minutes or until tomatoes are lightly charred and shallots are soft. Cool 10 minutes.
Chop tomatoes and shallots; place in a medium bowl. Add remaining 1 tablespoon oil, vinegar, and remaining ingredients to bowl; toss well.