1Fill a large pot with lightly salted water and bring to a rolling boil; stir in tortellini. Cook uncovered, stirring occasionally, until the tortellini float to the top, 5 to 6 minutes. Drain and rinse with cold water.
2Place tortellini, cherry tomatoes, and pesto in a large bowl; toss until evenly coated.
3Skewer one tortellini and one tomato on each toothpick. Arrange on a tray. Keep refrigerated until serving.