In 3 seasons, the Race commenced and ended in the similar town: Season 1 (New York City), time six (Chicago), and year 9 (Denver) only in Season nine was the Starting Line and Finish Line in the very same location: Red Rocks Amphitheater. Rolling Stone. New York City. Most routes in The Amazing Race circumnavigate the world, setting up from 1 American metropolis and ending in one more.